Something Better

by: Gingerfred Man

 

Chapter One – Pretty Good

My life lacked spark.

Oh, I had everything most people my age say they want. I had graduated from a pretty good college and had a pretty good job for a 26-year-old guy. I was writing copy for an advertising agency and the best part of that was, there were plenty of young babes around.

My name is Jerry Simmons. I liked women a lot and for the most part, they seemed to like me. I was a pretty good-looking guy, but kind of a runt – five-foot-eight and very slim. That ruled out most of the tall chicks, but even they often thought I was charming enough to see what I was packing in my boxers.

I had a pretty good set of equipment there – a fat, seven-inch cock and big, heavy balls. Word got around among the women and I usually had company when I wanted it.

Still, while I enjoyed the sex, something was missing.

Even though I was an alleged grown-up, with access to pussy, I still liked good porn. Not the flabby, 35-year-old-"teens" looking bored as tattooed stallions with beer guts penetrated them. Not the written-in-five-minutes novels where the kid discovers his mother and sister are both hot for him and he tries to see how long he can make the sentence, IIIIIIIIIIII’MMMMMMMM CCCCCCUUUUUUUMMMMMMIIIIIIIIIIIIINNNNNNNNNNGGGGGGG!!!!!!!!!!.

I liked the stuff that fired my imagination. And filled in the gaps between my fantasies and reality. It was rare, but it was out there.

One day, I was at my local newsstand, perusing the "adult" section as I often did. Hmmm. The latest issue of "Private." I loved those European babes with their gorgeous, beautifully made-up faces and tiny titties. I wasn’t much for the gangbangs they usually got themselves into and they didn’t wear stockings quite as much as I liked, but overall, you can’t lose with a classic. The girls had just enough titty to jiggle when they walked, which I found to be plenty. And they did all the things the girls I knew didn’t do. They looked so happy when the guys ruined their make-up with huge loads of cum. And they took any and all cocks up their asses while smiling prettily right at the camera. I had never fucked a girl’s ass or made cum in a girl’s face. I had only blasted cum into a girl’s mouth once and it made her really angry. Where were all those "Private" girls when you needed them?

Hey! There was the latest "Leg Show." I loved women’s legs in stockings. Not pantyhose. Preferably black stockings. Seams and reinforced heel and toe were big plusses. With sexy, very high heels. Hooked to lacy black garter belts. I was a traditionalist. The feet pictures don’t do much for me, but you can always count on four or five really good stroke pictures of beauties with stockinged legs and gaping pussies in each issue. The women I knew wore pantyhose or sweat socks or kept their legs bare. I had suggested that a couple of them wear stockings and they once again took offense. Why can women tell us what they want, but we can’t tell them?

The "Private" and the "Leg Show" should be enough for an evening’s entertainment, I thought, when I saw a book I hadn’t seen before. It was wrapped in plastic, so all I could see were the covers, front and back. It was a comic book in a large format, published by someone called Spermco. What moron thought that name up? It said it was part of a series called "Young Lovers" and the artist was someone named Teri. Probably some sweaty guy in his basement drawing with one hand and punishing Elvis with the other.

But the artistry was excellent. Although it was only line drawings, the detail was unbelievable. And the people were very good-looking. The book was called, "Hard at Work," (Get it? They were "hard" while they were at work.), a name that suggested a certain lack of subtlety and, perhaps, long-inbred stupidity by the author. Still, as I looked a little more closely, I was drawn in by the characters. An incredibly beautiful young woman, with a world-class figure and wearing a lovely miniskirt and six-inch heels, was standing face-to-face with a 35-ish, good-looking man in a business suit. He appeared to be talking. She was taking notes. His pants were bulging in an obvious erection, which would have been my condition facing that mega-babe. Wow, she was drawn well!

What made it strangely attractive was that, unless I was looking at it wrong, tenting her skirt just a bit, appeared to be the beginnings of her own erection.

It couldn’t be. That was sick. Icky bad. Gay, even. Gay as a carnival! But maybe it was worth the $4.95 cover price just to prove myself wrong. And I could always use it to wrap fish. I flipped to the back cover. Oh, no! The guy was standing there naked with his arm around the girl, who was also naked except for some incredible black lingerie and those sexy shoes. His cock was dripping cum and his whole pubic region was covered with the hot goo. Her face was covered with cum, as well as her big, mouth-watering titties. And she did have a cock! A big one that was also drooling globs of cum.

My knees were weak. I knew I shouldn’t buy the book. I looked around. Had anyone seen me pick it up? I should put it down right then. My cock had other ideas about that. I had a raging erection. I wanted to be alone with that comic book.

Guiltily, I took my "Private," "Leg Show" and "Hard at Work" to the Indian guy who owned the place. Would he glare at me, mark me down as a pervert, and request that I never come back to his newsstand again? He opened his mouth and said, "$34.85, with tax, please."

Whew! I paid him and hurried to my car.

The urge to unwrap "Hard at Work" was strong, but masturbatory proprieties must be observed. I never inspected my pornographic purchases until I had prepared myself properly. I walked into my apartment slowly, even checking my mail and straightening the kitchen a bit. Pleasure delayed is pleasure enhanced, after all.

I took the new purchases to the bedroom, unhooked my phone, and stripped to my undershirt. I opened the night table and removed a half-empty jar of lubricant and a roll of absorbent wipe-ups. Normally, I would read the lesser of my new literature first, stroking myself with lubricated fingers and thumb, exciting myself with wild surmise. If I felt the big event’s early warnings, I would break off, sometimes several times. Then I would approach the "closer" material, which was generally happy, gorgeous, cum-faced girls in stockings. Looking at me. Wanting my cum. Like the kind that would leap from my balls when I made the right conjectures in my mind.

Unless something changed in my life, I would always be like almost any other guy. The only way I would realize my all my sexual fantasies would be from good porn.

Different guys had different fantasies, but there were common themes. That’s why the most common phrase in porn is, "Suck it, Bitch," followed closely by "Take it all, Bitch." Only guys with mullets really call women that nasty name. But what is really being addressed is men’s fantasies that they be in control of women and that women be submissive to them.

That was the biggest fantasy of them all.

Women control sex. Normal, decent men don’t force women to have sex. So women dictate the terms. And they’re tough negotiators. Men want 100% of their fantasies fulfilled. They settle for about 25%. Cumulatively. In their lifetimes. The other 75% they get from good porn. Women have the power to give them almost the entire missing 75%, most of it with little or no effort or discomfort. But they don’t, because it’s all about power. Women have it. When they give guys what they really want, women see that as giving in.

As I opened "Hard at Work," I could see that the girl in the comic book wanted to help her guy reach that fantasy end zone and score several times. In the first panel, she was sitting at a computer desk with her incredible, black-stockinged legs crossed. Her mini was so short, you could see her garter snaps. Her heels were six-inch stilettos and you could see her painted toenails through the straps of her shoes. Her monster boobs were pushing the limits of her soft, tight sweater. She had big, blonde hair and big, blue eyes. Oh, mama, was she pretty. Her girliepole was tenting her skirt just a little, as she gave the good-looking man in her doorway a bedroom look.

What the heck was she doing with a cock? And why did it excite me so?

The caption was:

- Jessica, can you find something in my file, please?

- Yes, Mr. Simms.

In the next drawing, Jessica swayed into Mr. Simms’ office. There was a full-clothed, frontal view of this sex machine in motion.

In the next, Jessica was bent at the waist, tottering on her heels and rummaging though a floor-level file drawer. She was giving Mr. Simms a beautiful vista. Her perfect ass was framed by her stockings and pushed out by her towering heels. Only wispy, transparent bikini panties covered her soft globes and her little pink pucker was quite visible. Mr. Simms, the rogue, had taken this as an invitation and had removed his penis from its confinement.

It struck me that Jessica was doing something I had never done in my life – sexual teasing. Men rarely tease. Women tease, but it’s another thing they don’t do right. Men love to be teased to a happy ending. Men hate teasing without the happy ending. Women usually tease without pleasing or don’t tease at all.

Enough of this philosophy. I wanted my balls drained, so I turned the page. On the left, Mr. Simms was on his knees behind Jessica. She was still standing and bent at the waist. Her panties were down to mid thigh and Mr. Simms was enthusiastically eating out her asshole. His manmeat was rampant. On the right, the view of the same scene from Jessica’s front showed her beautiful face contorted in sweet agony as her clitty erupted its sticky girlie goo. It was flying high and so was mine. I couldn’t believe the intensity of my self-inflicted pleasure. More than any issue of "Private" or "Leg Show." More than my last visit to the real thing.

Breathing hard, I staggered on through the book. I flipped through pages of Mr. Simms’ big, veined, hard pole penetrating Jessica’s tiny pucker pit. Her expressions of love, lust and orgasmic trance were the kind I had always wanted to see on my bed partners. And the cum she spilled! Eruption after eruption. Mamma Mia!

It was a comfort for a man to have such visual evidence that his lover was pleased. You can’t fake sploogee

When Mr. Simms’ balls exploded into Jessica’s perfect tushie, her smile was that of an angel. Oh my, I was hard again, less than five minutes after a complete evacuation of my testicles.

Mr. Simms was stripped naked and Jessica was sitting on his lap. They were kissing as they stroked each other to creamy emissions. That did it for me. Zowie. I was hit by the Cum Tornado yet again.

What the heck was wrong with me? Looking at this "gay" stuff and blowing my goo all over the place from it. The girl had a cock! It was really two guys fucking wasn’t it?

Confused, exhausted and covered with cum, I turned off the light and went to sleep.

 

Chapter Two – Pretty Confused

I avoided looking at "Hard at Work" the next morning, so I managed to get to work on time and only thought about it 90 or 100 times that day.

After work, as I did every Tuesday and Thursday, I went out for a few brewskies with my friends Tony and Mark. They were guys I had known since high school and we always enjoyed each other’s company.

Tony was about my size, but Mark was a big guy, 6’3". Tony was working for a brokerage firm and Mark was a brand new psychologist. We were three young, single, square guys, so naturally we talked about women, our work, women, sports and women.

We ordered our first round of suds and Mark asked, "Remember ‘The Muppet Movie’?"

This appeared to be off-topic, but Tony and I warily said, "Yeah, sure."

Mark went on, "Remember when Fozzy Bear and Kermit sang that song about women?"

"The Muppet Movie" talked about women? We gave Mark blank stares.

He persisted. "Sure. You remember. They sang:

You can’t live with ‘em.

You can’t live without ‘em.

There’s somethin’ irresisti-bullish about ‘em.

She made a monkey out of old King Kong

I hope that somethin’ better comes along."

I did remember. And so did Tony. We said so.

Mark took a big pull on his beer. "I always thought the song was cute, but stupid. How could something better than women come along? And if it did, what would it be?"

We thought about it. Tony said, "They would be mute, and only use their mouths for sucking cocks."

I chipped in with, "They would talk, but only to beg for more cock in their mouths, pussies and asses."

Ah, the hilarity when witty men assemble.

"OK, that’s the first set of ideas," Mark said. "Now what would we really want women to be like?"

Tony offered, "They would be less stingy with sex."

"And willing to give in proportion to what they get," I said.

Mark, ever the psychologist, said, "What do you mean by that, Jerry?"

I said, "Last week, Jill was over for dinner. She wore sweats, sneakers and no bra. We talked after we ate and she seemed ready for sex. We had done it a few times before, but I thought I would be a good guy and ask her what she really wanted. She said she would like me to lick her pussy until her clitty poked out, then suck that little guy until she had a screaming orgasm or two. I’m only so-so about eating pussy, but I eased off her sneakers and sweat pants, pulled down her panties and dove in. I did a hell of a job, if I do say so, and Jill had four screamers. She finally begged me to stop. When she calmed down a little, she pulled me on top of her to fuck her, like we always do. I said, ‘Don’t you want to know what I would like?’

"The truth was, she didn’t. But she asked perfunctorily what I wanted. I said I wanted to cum in her mouth. Now remember, my face is soaked with pussy juice from an hour of eating her out. What do you think she said?"

"I know. I know," Tony said. "She said, ‘Ewwww!’"

We all laughed. Tony had nailed Jill’s comment verbatim.

Mark said, "And how did that make you feel?"

"So Mark," I said, "You’ll do this shrink number on us from now on?"

"Do you think I will?"

"Fuck you, Jerk-off. Anyway, it pissed me off, because it just isn’t fair."

Tony said, "Women aren’t fair. Maybe something better will come along."

We ordered the next round.

 

Chapter Three – Pretty Unlikely?

The next day, I kept asking myself, was a woman like Jessica of "Hard at Work" possible? I had never thought of it before. But suddenly I needed to know.

I’m not much of a computer guy, but I borrowed a laptop from work and took it home. After a few stops and starts, I got onto the Internet and looked up transsexuals in a search engine. My ignorance about the subject was astounding and so was the amount of information available on the net about it.

According to what I learned, Jessica was what was commonly called a she-male. There appeared to be several million pictures of she-males on the Web. I think I saw most of them over those next few days. Many were not the kind of girls one would bring home to mother, but quite a few were gorgeous, feminine lovelies, with all the charm of a girl and a cock and balls as well.

But were they just women with appendages? Did they act like women or something better?

And then there were the crossdressers, who didn’t grow their boobs, slim their waists and flare their hips. They dressed like women, but lived most of their lives as men. There was a lot about them on the Web as well. The hitch was, they dressed like women, but most claimed they only did it for the feel of the clothes. They didn’t want sex with men. They were :male lesbians." And Bill Clinton didn’t inhale.

So confusing. And why did I care?

After two weeks of carpal tunnel syndrome, I saw something that interested me a lot. In a chat room, I discovered that there was a club in our town that catered to TGs (the inclusive term) and their admirers. There was a cover charge, but I was going.

On Friday night, I put on a blue suit and brushed my hair. I got there around eight and there were about forty people in the place. Only three of us were dressed like men, but my guess was, we were all men. I was feeling very out of place and was thinking about bolting when a sweet voice behind me said, "Hi. Are you new here?"

I turned. A very pretty young woman in a blue dress smiled at me. A nice smile. Long, straight, brown hair and gorgeous brown eyes. Best to be wary, though, I thought. This could be a man!

When I stood there staring, the young woman said, "My name’s Gina. I don’t believe we’ve met." And she extended her hand.

I shook it and said, "Jerry, and yes, I am new."

Gina was not shy. "Do you dress?"

I was puzzled at first, then caught on. "No. Never. I mean, not that there’s anything wrong with it."

"Then why are you here?" Gina asked pleasantly.

Good question. "I’m curious," I answered honestly.

Gina eyed me up and down. When she decided I wasn’t here to look at a freak show, she smiled. "Well, I’m glad you are. Can I introduce you around?"

I thanked her, and she did show me to everyone. I met lots of ladies that night. Some were pretty. Some were pretty ugly. But they were all pleasant and charming. And remarkably feminine. Gina giggled at my reactions, then cut me away to talk.

"What did you think?" Gina asked.

"Nice people. Normal."

Gina liked that answer. "Do you think I’m normal?"

"A lot better than normal," I said. It was the right answer.

Gina told me she was 25 and had been dressing since she was 12. She had taken some hormones and had had a few small surgeries here and there, but most of what she had was natural. She had dressed full time since she was 21.

I gathered the guts to ask, "Do you like men?"

"Nice ones," she answered with a pretty smile.

I asked her out for dinner the next night and she accepted.

Maybe something better had come along.

 

Chapter Four – Pretty Girl

I picked Gina up at seven and we had a great date. She was wearing a lovely pink dress with short, pleated skirts, silky stockings and towering heels. She oozed femininity. I couldn’t wait to show her off. I took her to an Italian restaurant in my neighborhood and introduced her to a lot of people I knew. They all gave me the sign like, "You got a good one, there Jerry. Hold on to her."

Gina was delighted that I did that, rather than sneak around dark spots with my TG, so that no one would see her five o’clock shadow. Which she didn’t have, by the way.

We talked a lot about our lives and what we liked and didn’t like. Gina was an accountant for a big firm. Her parents were very supportive of her gender orientation, as was the rest of her family. She had had a few boyfriends, but nothing serious. Just like me.

I took her home hoping for a kiss goodnight, when she surprised me by inviting me in for coffee. She put the coffee on, then excused herself for a moment. When she came back, twelve minutes later, she had lost that pretty dress and slip, had gained some eye shadow and perfume and was standing there in a long, diaphanous peignoir, her bra, garter belt, stockings, heels and very full panties. Oh my. She had an extraordinary cock and whatever she was hiding it in all night was gone. It was standing up and pointing at me. And dripping sticky goo. The thought "You are gay" crossed my mind as my mouth watered at that beautiful sight.

I looked Gina in the eyes and she melted me with a phasers-on-kill smile. My heart was beating rapidly, pumping every drop of blood in my body to my cock. It’s a wonder I didn’t faint.

I guessed I wasn’t getting that coffee.

I was ten times as excited as I had ever been with any girl. Gina sensed that and was very kind and gentle. She sat beside me on the couch and kissed me. With ample tongue.

"You’re a good guy, Jerry." Gina whispered to me. "There aren’t many of you out there."

I was flattered and horribly aroused. I kissed Gina again. Then I told her, "No one in my life has ever excited me as much as you have. You’re incredibly sexy, easy to talk to and intelligent." Darned if I didn’t almost ask her to marry me. Was I losing it?

Gina smiled. She knew I was sincere in my praise and she beamed with pride. "Let’s go in the bedroom, Jerry, and we can do whatever you want."

Whatever I wanted? Did she mean it? My eyes actually filled with happy tears.

Gina’s bedroom was a feminine shrine. Everything about it was ruffled, lacy and girlie. This was what I wanted. A real girl. She shucked off her peignoir, then lay on her back with her stilettos still on. That was a nice touch. Then she wiggled seductively and teased the head of her, I guess you would call it a clitty. She was using her index finger to elongate strings of pre-cum, smiling at me as she did it. Excellent teasing!

I got the picture and removed my clothes from my runty frame. When I pulled off my boxers to expose my fat cock, Gina said, "Yummy!"

Yummy? No girl had ever said anything like that to me. She was a whole new kind of girl.

I lay next to that new kind of girl and kissed her. She purred her appreciation. Wow. I peeled her bra, exposing her fantastic titties. I kissed them all over, licking and worshiping the nipples. She squealed with pleasure. "Tell me what you want," I said.

She groaned, "I want to please you."

My goodness. Was this possible? A woman who wanted to please a man who wasn’t a multiple felon or a porn star?

Gina had a pretty good idea of what I wanted. She got on her knees on the bed, sitting back on her spikes, and skinned my prick. She gasped in appreciation, as if it were the first cock she had ever seen. The pink head of my little friend was turning purple with blood and excitement. Gina held my balls in her other hand, hefting them and exploring them with wonder. She made a thorough inspection as I squirmed with lust and the tiny bit of fear one has when his balls are in the hands of a virtual stranger.

No need to worry. Gina’s intentions were loving. She kissed my cockhead, leaving a little lipstick stain that I vowed never to wash off. Then she licked it. Cowabunga! What a tongue that girl had. She giggled at my reaction, then tongued the lips of my peehole. Ohhhh! I thought she was about to begin sucking in earnest when she stopped. Oh, no. Had reality slain me again?

Not this time. Gina licked the index and middle fingers of her right hand and gently inserted them in my ass!!!! Ahhhhhhh! I arched my back and groaned loudly. I had never had anything in my ass before and it was fantastic! I almost blew my load then when her lacquered nails scraped my prostate. But the show was only beginning. Gina pistoned her fingers in my spasming butt as she capped my cock with her beautiful mouth. I was the ruler of one of Heaven’s larger continents. Everything was going beyond my fantasies. How many of us can say that?

Gina sucked and pistoned. She rubbed her cheeks against my cockhead, wetting them with the drooling stream of pre-cum. She even tickled my balls with her free hand. I warned her that I was cumming. I certainly didn’t want to anger this once-in-a-lifetime angel. She smiled at me with her eyes and kept at her business. I was going to cum in her mouth! And she wanted it. Oh! Oh! That anal stimulation! I thought that was only for gays. Oh! Oh! Who cared? My cum attack built and built and RIPPED my gut. I felt a quart of manly juice evacuate my balls and Gina sucked it down happily. Who was this girl? I did want to marry her. And make love to her forever. Gina sucked up and swallowed the last drop as my ass convulsed on her wiggly fingers. She smiled and moved up for a big kiss. I gave her my tongue and licked some of my own cum from her mouth.

At a minimum, it was time for some rethinking on my part regarding all my ideas about sexuality and gender. But that was for later.

For now, I wanted to make Gina happy. I kissed her with all the love and passion I could muster.

Which was quite a bit.

I peeked at her cock or clitty or whatever it was. It was staring at me. And drooling sticky girlie goo. I wanted to suck it. I looked at my lovely Gina’s face. She wanted me to suck it, I could tell. An epiphany was imminent. I was about to cross a line straight guys believe they will never cross. I wanted to run past that line full speed, thumbing my nose at it.

Gina understood. She asked me to lie on my back. I would have stood on my head for her, so that was easy. She straddled my shoulders and pointed her drippy little girl at my face. The brown foreskin was back and the pink head looked like the most delicious thing on our planet. Her drooling semen was the only thing that could slake my thirst. I opened my mouth eagerly and Gina moved her clitty to my lips. I kissed it and moved onto my life’s better, higher ground. I was giving pleasure freely and eagerly to someone who would do the same for me. I licked the goo from its velvet head. It was scrumptious. Gina squeaked with pleasure. I was fatally excited.

Gina began to push her perfect cock in and out of my mouth, slowly at first, then more rapidly. She whimpered and squealed. Oh, how I loved that. I used my tongue as well as I could, then inspiration struck. I grabbed Gina’s hips and eased her clitty from my mouth. She whimpered a little until I licked two fingers, lathering them up with my saliva and Gina’s precious girl juice. As she did for me, I inserted first one, then two fingers into my dearest’s perfect ass. She quivered with lust and re-inserted her clitty into my willing mouth. I had never entered my own ass with fingers before, let alone a girl’s, and I had obviously never sucked a cock, but I knew what felt good to me, so that’s what I tried to do for Gina. It seemed to be working. I don’t think I had ever seen more appreciation from a girl. I loved the little noises, the gasps, the pants, the squeals. And I loved the sweet looks Gina gave me.

Then her beautiful eyes got very wide, she trembled, clenched her anal vise on my fingers, and came hard. Unskilled as I was, I’m afraid I allowed cum to spray. I swallowed what I could, but most drooled out of my mouth and flooded my cheeks. I loved the taste. I loved the intimacy. I loved the dirtiness of it all. I didn’t even mind that I was now officially a cocksucker. I would suck that sweet girl’s cock any time.

Gina was overjoyed with what we had done. She lay on top of me and kissed my cummy mouth and cheeks. I embraced her and kissed back. My bad boy was getting all naughty again. Then Gina said something that I wished I had heard more often from my bed partners.

"You’re an excellent lover, Jerry."

I was so proud of myself at that moment, I almost cried.

Then Gina said, "Would you like to put that nice poker of yours in my tight little pussy?"

Oh, yes. "Just tell me what I need to do."

"Will you lick me <blush> back there, so it won’t hurt me when you put that big, hot thing in me?"

Any walls you want me to run through, ma’am? "Yes, please. I would love to."

Gina said, "Just lie on your back and I’ll straddle your shoulders and face your feet. Then I’ll just ease my little pink pucker down on your tongue. Aaaaaaaahhh. Very nice. Just lick. Oh, you bad boy. You’re digging in with your tongue. Mmmmmm."

Excavation seemed like the right thing to do for someone who was making me so happy. I loved the feel of Gina’s perfect ass covering my face. It was creamy and smooth. It smelled like flowers in spring. And her little brown hole had become the center of my universe. I tasted it. So good. I licked it again. She liked it a lot. I loved pleasing this woman so much. I went for the gold, digging my tongue into her secret passage. She really liked that. I reached around and caressed her little pink bag of balls. They were very sensitive to my touch and the combination of things I was doing brought my new sweetie to a very powerful cum. Her ass involuntarily clamped on my tongue, but I survived. She actually screamed when she blew her girlie load into the stratosphere. Another first in my experience. I loved that too.

When she regained her faculties, she kissed my chest, licking my nipples and praising my lovemaking. The nipple adoration was another first for me and my big boy was purple once again. I was discovering all kinds of new things that I liked. Gina was a fantastic tour guide.

Gina broke off, moved to the foot of the bed, and lay on her back. She brought her stockinged ankles to her ears and begged me to fuck her NOW! Another fantasy checked off the list.

For the best angle, I stood and presented my cock for its first visit to the servant’s entrance. Gina was crying and begging to be fucked. Wow! I was afraid I would hurt her, but Gina knew a thing or two about anal love. My rampant friend entered her easily, all the way to the hairs on my pubes. Gina moaned loudly and repeated her desires for a good fucking. Yes, ma’am.

I gave Gina what she wanted. She was frantic with sexual heat. I felt like the biggest stud on earth. And the luckiest. Anal fucking was outstanding. Everything I had dreamed about and more. The grip was different and it was drier, but it was so tight and so……dirty.

It seemed like the right thing to skin Gina’s willie as I shagged her, so I did. Her eyes widened with admiration and, I hoped, love, when I did that and darned if she wasn’t naughty again. She sprayed her cream on her sweet tummy and beautiful titties. And the clench of her ass muscles when she came almost snapped my cock off. In a good way.

Two minutes later, I was near my own grand crisis and Gina leaned her head up to kiss me. I leaned down and we swapped tongues. It was …..so…..Oh…….very…..Ah….. erotic. Beyond anything I had ever imagined. I was confused. My balls, however, were not. They followed their instincts by violently spewing a month’s worth of manly seed into my dearest Gina’s pretty bottom. I groaned with joy. Gina squealed as she felt the cum enter her bowels. It was the best 20 seconds of my life.

When Gina’s anal passage involuntarily discharged me, we lay cuddling and kissing for an hour.

I had seen something better and I wanted it forever.

But the evening held a couple of more delightful surprises. I would have stayed there kissing Gina until they pulled our starving carcasses apart, but she had other ideas. She retrieved her discarded silky panties and wrapped them around my re-invigorated charger. Now after a five-star blowjob and a six-star assfuck, you may view this mere handjob as anti-climatic. But it was incredibly erotic.

I had never received such a skilled, loving handjob, even from myself. And the feel of the panties, Gina’s own panties, on my poor, assaulted cock, was fantastic. So this was why women wear panties, I thought idly, as I relished the loving attention. Another advantage they own over us. Mmmmm. That was good.

Gina said, "Do you like the feel of silk on your big, hard clitty, Jerry?"

I didn’t have a clitty, but the idea was correct. I said, quite articulately, "Mmmmmmm."

"You’re a wonderful lover, Jerry. And a good guy. You deserve so much more than life is giving you. You didn’t want much from women. Only femininity. And they wouldn’t give it to you, right?" Rub. Rub.

"Yesssss."

"Do you like the silky, feminine feel of these panties on your best friend, Jerry?"

"Yes. Yes."

"Would you like to have femininity with you all the time? The femininity you love and can’t find."

"I would, Gina. I…..Oh, Gina…..<Groannnnnn>"

Where that third huge load came from, I’ll never know, but it saturated Gina’s panties and almost gave me a stroke. I looked at Gina. She was smiling her pretty smile and seemed very pleased. With me and with herself.

When it was time to get dressed and go home, Gina asked me for a special favor. "Would you wear a pair of my panties every day this week for me, Jerry? It would make me feel we’re together, even when we’re not."

How could I refuse? I slipped on a pair of blue nylon bikinis. They felt cool and incredibly arousing. I was getting another erection. Gina smiled, got on her knees, pulled down my panties and sucked and licked my fourth erection into the annals of history’s greatest orgasms. Her face dripping with cum, she kissed me good night and said, "See. Wearing those panties already paid off for you. And me."

We kissed some more and agreed on another date for Wednesday night. Her four other pairs of panties felt warm in my pocket. My smile was wide as I drove home.

 

Chapter Five – Pretty Good Advice

On Tuesday, I was the first to arrive for the semi-weekly therapy/bonding sessions with Mark, the good friend and trained, but inexperienced psychologist, and Tony, the good listener and better friend. I had a lot to talk about. How much I would say was up in the air.

I had been wearing the panties for three days and I loved them. It’s a wonder all men don’t wear them. They rub so nicely against your cockhead. I felt so excited with them on me.

Mark got there first and I asked for his professional cone of silence.

"Give me a dollar," he said.

"Why?"

"Because if you engage me as your psychologist, everything we discuss is privileged, even in court."

"Oh. OK." A bit severe, but I was OK with it.

"Now, what’s on your mind, Mr. Simmons?"

"Well, Dr. Asswipe, it has to do with the most fabulous woman I ever met. We went out on Saturday. Then we went back to her place and we did everything I’ve always dreamed of sexually. She’s gorgeous, funny and intelligent. She sucked my cock and swallowed my cum. I fucked her up the ass and she squealed with joy. She wears stockings and garter belts and extremely high heels. She’s the femmiest person in this state."

"I heard that from Joe Malloy. He saw you at Luigi’s with a babe way too good for you. But there’s a problem?"

"Well, I also sucked HER cock and swallowed HER cum."

Mark blinked in a very un-Freudian way at that one. "Oh my! And how did you feel about that?"

"I loved it! I love her. She’s everything I’ve always wanted in a woman. Who cares about the extras?"

"Do you think you’ve thought this through? You sound as if you want to marry her."

"That’s a possibility."

"After one date?"

"I’ve never felt this way before."

"Hmmmm," the young Freud disciple said.

Just then, Tony blasted in, so Mark and I stopped talking about my issues. Tony had spoken to Bigmouth Joe Malloy too, so he asked me all about Gina. I told him a lot, but not about the specifics of our sexual encounters or about Gina’s extra girlie bits.

"You’re a lucky guy, Jerry," Tony said. "Don’t let Gina get away."

I had no intention of doing so. I saw a look of quiet interest on Mark’s face. Maybe he and I could talk about it Thursday, I thought. That next night, I would be visiting my angel again.

 

Chapter Six – Pretty Things

Had I found everything I really wanted in Gina? That was what I believed when I knocked on her door that Wednesday night. The darling, dishy delight greeted me wearing a tight, little black dress with black stockings and five-inch-stiletto fuck-me pumps. She looked and smelled like a dream come true and her smile would have melted reinforced steel.

I wanted to fuck her right there on her front steps, but settled for a lipsticky, tonguey kiss that erected me fiercely. Down boy. Later.

For dinner that time, we went Chinese, in Gina’s old neighborhood. Like me, she knew a lot of people and they all stopped by to say hi.

I asked, "Are these people who knew you growing up? As a boy?"

Gina smiled. "I was never a boy, Honey. I only dressed like one for a while. People I grew up with have been wonderful. I was good to them and they accepted me for who I really am."

This girl was very easy to love. I opened my fortune cookie. "You will find your heart’s desire," it said. I read it aloud to Gina and added, "That’s you. I’ve found you."

She smiled again. "Yes you have. But am I really your heart’s desire?"

Why wouldn’t she be? What did she mean? I asked her.

"Maybe I’m just a way for you to find your heart’s desire," she said cryptically. "I really don’t know, but I want to help you find out."

That was odd. Oh well, I thought. Nobody’s perfect. Even Gina, I guess.

As we drove to her place, Gina asked me, "Are you wearing my panties?"

"I am"

"Which ones?"

"The pink, nylon, translucent g-string."

"And do you like them?"

"I do," I admitted honestly. "I prefer them to men’s undies very much."

"Hmmmm," my darling said.

When we got to Gina’s, I was ready for more of the best sex I had ever had. Gina asked me into the bedroom. No pretense of coffee this time.

"Please unzip me, Jerry."

I did so, with gusto. Gina peeled off her dress and shimmied out of her slip. I hoped I wasn’t drooling. She removed her bra and her warm puppies breathed free. Wow. I removed my clothes, peeling off my panties to reveal little Jerry standing at attention. Gina licked her lips. It didn’t get any better.

But before we dove in, Gina asked for a small favor. "Since you liked my panties, would you wear a pair of my stockings? I’ve always wanted to know what stocking-to-stocking felt like during sex. Please? For me?"

Strangely, the idea of wearing stockings during a hot sex session sounded wildly appealing. As long as, you know, it was Gina’s and my little secret. I agreed immediately, then hoped Gina didn’t think I was some nancy-boy.

She kissed me and said, "You don’t know how happy it makes me that you want to please me. Now let’s just go in the bathroom and shave off all that nasty hair."

I looked puzzled and reluctant. Gina said, "You can’t wear stockings with hairy legs, Silly."

Of course not. What was I thinking?

Gina sexually teased me unmercifully as she shaved my legs. She would stop frequently to suck my cockhead, then back off when I appeared close to eruption. She tickled my balls and kissed my mouth too. As she was shaving my thighs, she had two wiggly fingers up my ass and that almost did me in. She knew it was torture because she giggled the whole time. Still, I must admit, I enjoyed the intimate attention she gave to the shaving as much as I did having my cock sucked. I loved being all smooth from the top of my thighs to my toes.

I was frightfully warm when Gina handed me two doughnut-rolled stockings to slide up my legs. She kept talking as I eased the right stocking up, telling me how good my legs looked and how much fun we would have rubbing our legs together when we made love. Oh, Baby, that was hot. When I got the second stocking up, I was trembling with sexual fury.

Gina said, "Those stockings will roll down if you don’t wear this pretty garter belt." And she hooked me to it. Then she walked to her full-length mirror and beckoned me to see myself.

Oh my goodness! I saw a full frontal view of myself in stockings and a garter belt and my cock twitched. It was pouring out sticky pre-goo.

Gina stood behind me and we looked at ourselves in the mirror. She reached around my right hip and pulled my foreskin back ever so gently.

"You look fantastic, Jerry. With a little bit of make-up, you would be a stunner. I’m more attracted to you than I ever was." Skin. Rub. My hips jerked and I felt the first big warning.

"Just think how you would look," Gina continued, "In a pretty nightie. All that silk and lace. Rubbing against you."

Oooooohhhhh! My hips bucked. Gina stroked me harder. SPURT! A huge glob of hot cum hit the mirror.

"Let it out, Jerry! Good girl!"

Girl? I…Ohhhhhh! ANOTHER HUGE SPURT. My knees buckled. AND ANOTHER. Gina squealed happily. AND ONE MORE. My whole lower body vibrated in delicious agony.

And then the unthinkable happened.

I squealed.

And it felt really good.

 

Chapter Seven – Pretty New at This

As good as I thought my first date with sweet Gina had been, my second was even better. I loved wearing those stockings to make love. It didn’t mean I was gay or anything. I just liked the clothes.

The stockings allowed me to give Gina a treat that I had often imagined. We sat on opposite sides of her couch and I rolled Gina’s clitty between my warm, stockinged feet until she came hot gooey buckets on my nyloned tootsies. It was good messy fun and Gina enjoyed it so much that she returned the favor. <Shudder> What a ball-evacuator!

The feel of the nylon on my bare legs was addictive. In fact, I decided that I would wear stockings and a garter belt under my guy clothes for a while, just to see if I liked them. And the panties of course. You know. Just to see. If I liked them. The panties. And the stockings. And garter belt.

I wore them to work the next day and was in a constant low state of panic that I would be "caught" and a constant medium state of arousal as I thought of how sexy my naughty little secret was. I began to wonder if I was the only guy wearing pretty pink panties and seamed black stockings with a lacy garter belt. I found myself checking out my co-workers’ pants, which I thought I had done subtly until I got an odd stare from my boss, Brian Callison.

Brian was a good guy for a boss. Very creative himself and supportive of our creativity. And interested in the welfare and development of his subordinates. He was about 35, good-looking, and had girl friends, but was still single.

"Everything all right, Jerry?" Brian asked that day.

I must have looked really spaced. "Oh, sure, Brian. I’m just thinking through the copy for the Fudgie Wudgie campaign."

"OK. I just thought you looked pre-occupied. Please let me know if I can help."

What a good guy. "Thanks, boss."

That night was our regular attitude adjustment Thursday and I showed up early again, hoping to catch Mark before Tony arrived. I was there about five minutes when the bartender told me that Tony was sick and couldn’t come that night. I would have Mark to myself. All right!

The young shrink arrived moments later and seemed happy that we could talk by ourselves. I think he was beginning to view me as an interesting subject as well as his friend.

"So what’s new, Jerry?" he asked.

"I’m wearing stockings and a garter belt as well as panties, Mark," I announced.

Mark looked fascinated. "How did that happen?"

I told him.

"How do you feel about that?"

I considered my answer. "Liberated. I feel that the old rules are dead and I like where the new ones are taking me. I’m having great sex and I’m exploring places I never thought I would go."

"Um hmm. Any reservations?"

"I don’t want to be caught, because most people wouldn’t understand. They would think I was gay or something."

"Are you gay or something?"

Two weeks ago, I would have smacked my friend for that question. That night, I gave it a serious answer. "I don’t think so. I have no interest that I know of in men, but I’m wearing women’s lingerie and I’ve been sucking a pretty girl’s cock every chance I get."

"Would you want to get dressed completely in women’s clothes?"

I hadn’t thought of that and said so. Then I added, "It would be interesting, I think."

"Um hmm. Why do you think Gina is dressing you like she is?"

"Good question. I think she wants me to be happy and she knows what made her happy. So she could be projecting her own preferences onto me. Or maybe she just wants me to see the world before I settle on where I want to live in it."

"Those are very mature answers, Jerry. You’ve changed a lot in the last few days."

"Thank you, doctor. Now let me buy you a beer and you can tell me what you think I should do."

"You know better, Jerry. All I can do is help you solve your own issues. What do YOU want to do?"

"I want to see where this is going, one step at a time."

"Um hmm," my non-directive counselor opined.

 

Chapter Eight – Pretty in Pink

My next date with sweet Gina wasn’t until Saturday, so on Friday night I was home alone. I got home from work around six-forty-five, checked my mail, and microwaved a Lean Cuisine. I wanted to stay slim for my Gina.

Then I went to my bedroom and took off my work clothes, leaving only my undershirt, panties, garter belt and black stockings. I shucked my undershirt and put on a pastel blue tank top that I hadn’t worn much. Then I dared a look in the full-length mirror. Man, was I hot! I didn’t look like a man or a woman, but I looked like someone anyone would want sex with. My poor prick was very agitated and bulged my panties in fiery expectation of relief. It was fully my intention to relieve him often that evening.

I wondered how I would look in high heels. The kind Gina wore. I turned my ass toward the mirror and stood on my tiptoes. Wow! My ass stuck out in lewd invitation and my legs toned beautifully. I considered my ass, framed by garter belt and stockings, and my cock twitched. I was being ignited by my own butt. My cock was insistent, so I teased the head with my thumb and two fingers, thinking all the while how hot I looked and conjecturing wildly about where all this was taking me. Oh. My cock knew its agenda. My balls were boiling over. I grunted manfully, then squealed like a little girl as cum blasted from my pee lips. I squealed again and tears filled my eyes as successive blasts erupted and pleasure saturated my loins. I was acting like a girl. Like that girl in the mirror. The shame of it. The raw, sexual excitement of it.

I lay on my bed gasping and panting. After a bit, I reached for my nightstand and extracted three things – paper towels, personal lubricant and my cum-stained copy of the culprit behind all the changes in my life, "Hard at Work."

My perspective had changed since I bought it just a couple of weeks ago. I wanted to see what that meant when I looked at it again. Plus, I wanted to blow a few more nuclear explosions before I passed out.

I turned to a page where Mr. Simms had Jessica on her back. Her ankles were on Mr. Simms’ shoulders and the expression on her beautiful face was blissful. Mr. Simms had his big cock in her pretty pussy hole and he was in full orgasm. The sweet strain on his face was so charming. Cum was oozing from Jessica’s stretched rosebud. Jessica was engaged in her own orgasm and her girlie cream was sprayed all over her flat tummy and garter belt.

I had lived Mr. Simms’ experience during my two fabulous dates with Gina. I wondered what it would be like to be Jessica, with that big cock up my ass. I put down the book, gooed up two fingers of my left hand and eased them into my tight, virgin ass. Aaaaaahhhhh. What if that were Mr. Simms’ cock and he were on top of me, kissing me, loving me? Making me his girl? Ready to send his seed up my tiny butt? My cock was rampant and jerking. I touched my clitty’s boiling head. I moved my fingers in and out of my clenching "pussy." In and out. I was just a little girl and Mr. Simms was dominating me. Fucking me. I couldn’t get away. I didn’t want to. I was in paradise. I …..Oh….my juice was boiling. My balls wrenched. My toes exploded. Thick ropes of hot cum flew two feet, all over my tank top. Oh, Mr. Simms!!!!! Oh, Jerry. What the heck was happening to me?

The next day, all I could think of was my date with Gina. She asked me to come by at around two, so we could make a day and a night of it. I was all for it.

I shaved my legs. Who wanted that ugly stubble? And I put on a pink garter belt and stocking set that Gina had let me borrow. I was going to have to get to the store soon and get my own things. I looked at my butt and legs in the mirror. Not bad, but I really needed pink mules.

I slipped on khakis and a polo shirt and drove to Gina’s. As usual, she was incredibly happy to see me, kissing me desperately, hungrily.

We went inside and kissed some more. "I have some surprises for you this weekend," Gina gasped between kisses.

This weekend? That must have meant I was staying over. Excellent!

"Let me see you," she said. I stripped to my pink things and Gina gave a little gasp of appreciation. "Oh, you look beautiful, Sweetie. How do you like wearing those things?"

I hung my head a little and said, "I didn’t think I would, but I love it. It feels so sexy to me. I worry about being gay, though. But I’m wickedly attracted to you, so I know I can’t be gay. Right?"

"Of course, Jerry. I knew you would love the clothes. I didn’t want to deny you the opportunity to find that side of yourself. Anyway, gay, schmay. Who cares? You’re having fun, right?"

"The most ever. Are we going to have fun today?"

"All the fun you want, Honey. And you can stay over if you like."

I was quivering with desire for this lovely woman.

"Remember, Jerry. Surprises and new things, and here’s the first."

Gina reached into a department store bag and pulled out a wispy little pink nightie. "Can I see you in this, Sweetie?"

I couldn’t believe how excited that prospect made me. I accepted her thoughtful gift and slipped it over my head. I padded over to the mirror in my pink-stockinged feet and gasped when I saw how hot I looked. It was barely long enough to cover my goodie bag. The silky material rubbed against my erect nipples. Oh, my. Mr. Johnson was very angry down there. He was about to spit.

Gina had stripped off her dress and was now wearing a nightie that matched mine in design, but was black like her lingerie. She glowed with pleasure at my reaction to the femmy clothes I wore. "You’re a major hottie, Jerry. We’re going to love each other within an inch of our lives this weekend. But look how excited you are. That must be very uncomfortable. Let me help you."

Gina got on her black-stockinged knees, peeled my panties down and took me in her mouth. As I looked in the mirror, admiring myself in full narcissistic rapture, Gina gave me four luscious swirls around my clitty head. Why was I calling it that? I squeaked and panted, then made a deep-throated girlie scream when she sucked a quart of cum from my loins. Oh, my goodness, that was a cum storm! With 30-knot cummy winds. And a cum-boil factor of 98.6 degrees.

Gina was the most beautiful when my cum was all over her pretty face. I licked it off and told her how grateful I was to her and how much I loved her.

"I love you too, Jerry. You’re the best thing that’s happened to me in a long time. I have more surprises."

"Great." What was that number again? Nine-one-something?

Gina extracted a pair of pink mules from her bag. Oh, they were darling. I hoped they would fit. They did! I had some trouble with the three-inch stiletto heels, but after about 20 minutes, I got the hang of it.

"Go, ahead, Honey," Gina said. "Look at yourself in the mirror."

I did. And got another erection. I still needed make-up and a better hairstyle, but I was very girlie-looking. And sexy as heck. It made my cock twitch again as it does when I’m approaching naughtiness. Gina stood behind me, smiling once again. Then she startled me by entering my tiny butt with two greased, very talented fingers.

She found my prostate and gave it her full attention. I began to breathe very hard. Panting almost. I was so pretty. I loved being pretty. Gina reached under my nightie and tweaked my right nipple. I adored it. I breathed harder. My legs looked spectacular. And my ass looked so <blush> fuckable. Oh, those fingers in my tiny pooper. Oh, this girlie stuff. I wobbled on my heels and felt my balls simmering to a boil. Gina kissed my neck. She was so beautiful. Her fingers. Aaaaaah. My butt clenched her fingers and my balls evicted four greasy globs of my special reserve. Gina held me up. She was better in her five-inch stilettos than I was in my threes.

Mercilessly, Gina kept frigging my poopie hole. Even after I had abandoned hope of ever cumming again. And her industry paid off in yet another erection for me. I wanted to help my Gina cum. She suddenly maneuvered me, fingers still buried, to the side of the bed. Following her lead, I got on my knees on the floor and lay from the waist up on the bed. Now what? I thought.

Gina pulled her fingers from my butt. I whimpered a little. I loved her fingers there. I didn’t look behind me right away, but I could tell that Gina was doing something with her clitty. Why was she whacking herself, I thought. I would bring her off gladly. Unless… Would she? Could she? Was that all right?

A wave of fear ran through me. I felt Gina’s stiff little girl between my ass cheeks. She wouldn’t! I said, "Gina, are you…I mean I’m not sure if…."

"It’s OK, Jerry. You’re ready. You’ll love it, I promise."

I whimpered with fear. Gina spoke to me reassuringly. I felt her large mushroom at my minuscule sphincter. It would never……Aaaaaaahhhhh. Gina’s clitty head popped in. I squeaked. I was being fucked. My eyes filled with tears. It was wonderful. I pushed back for more of Gina’s hot, hard clitty. She grunted with pleasure. I squealed like the girl I appeared to be. She got it all in up to her pubic hairs. I felt no pain, only intimacy, sexual excitement and a strong urge to poop. I could deal with the last one later. I was enjoying the first two very much.

Gina seemed to be very skilled in every aspect of lovemaking. Even this surprising one. I guessed tgirls did those things with each other.

Despite my previous hard work, I was nearing another hard cum. Where was all this stuff coming from? Maybe all those Flintstones Vitamins were paying off.

But my first priority was to give Gina pleasure. I worked my ass muscles on her cocklet, just as she had done several times for me. She squeaked in appreciation.

"So good," she said. "Your ass is so hot inside. And so pretty. I can’t hold back. I have to cum. Eh-heh. Eh-heh. Eh-heh. Eh-heh. Aaaaaaahhhh."

I felt a flood in my bowels. Then I really had to poop. Gina was in ecstasy. She was wheezing with gratification. Despite imminent catatonia, she had the wherewithal to reach around my hip and bring me to a creamy conclusion.

Would I live through the weekend? It was touch and go.

As we lay side by side, kissing and cooing, I decided that I really needed Gina’s pricklet back in my lonely ass. The fact that it was covered with my own poopie didn’t deter me a bit from giving it the licking of its life. Gina was ragingly erect once again in minutes and had my tushie properly plugged in the spoon position soon after that. This time our coupling lasted a good half hour, although I could have stayed like that forever. When she screamed her joy and deluged my bowels. I cried uncontrollably with love and sexual excitement. Either I passed out or we took a nap. Or both.

We came to a couple of hours later and kissed some more. Gina said it was time for some food and a make-up lesson. Then she wanted to be fucked like the bad little girl she was.

I wasn’t sure I wanted the make-up lesson, but I really wanted the fucking.

Gina was a patient, excellent teacher. I learned about foundation and blusher, mascara, eye shadow and eyeliner, lipstick, lip-gloss and lip liner. It was an art as much as a science and Gina was an artist.

In all those TG stories I had read when I was doing my research, the new "girl" stares at the mirror in surprise and delight at how pretty she looks made up for the first time. I thought that was baloney until my moment came. I got a big boner just staring at myself in the mirror. Had I ever looked that good in my life? No. Too bad it was as a babe.

My hair was short, but my face was three-and-a-half stars pretty. My eyes were large and liquid. My lips were full, red and pouting for soft kisses.

I realized that this was getting out of hand. I opened my mouth to tell Gina that when she placed and fitted a long, brown wig on my head. My heart seized up. I was astonished at my now four-star beauty.

"You’re prettier than I am, Jerry," sweet Gina said.

I poo-pooed it, but she was right. I was most babish.

But I was a guy, wasn’t I? Or is that just a dumb label.

"What do you think, Jerry?"

I looked at the mirror, then looked at Gina.

Gina said, "You’re scared, aren’t you?"

I nodded.

"It’s OK, Honey," Gina said. "I understand. You had no idea about this side of you. Now here it is."

Gina was exactly right. I said, "Why did you bring me to this? Couldn’t I have just been your boyfriend?"

Gina looked sad. "I would have loved that, Jerry. But you wouldn’t. You would be restless and would have ended up where you are today, only a few years later and a lot angrier at the world. I suspected you were a TG the first night I met you. Being around me would have brought out the desire. I just decided to see if it was true as quickly as I could. If it weren’t true, I would have been happy to be your girlfriend."

My heart sank. "Is it over between us?"

Gina giggled. "Of course not, Honey. I love you very much. I’ll be your girlfriend for as long as you like. And you’ll be mine."

That sank in. "So we’ll be like a lesbian couple."

"Yes, but we won’t be exclusive. I like men and I’m going to have sex with some nice ones whenever I meet them."

The roller-coaster went down again. Gina didn’t consider me a man.

She saw my soul and said, "You’re one of us. Not a man or really a woman. Something better. But I need men. And I think you do too."

I was horrified. "Gina, I could never have sex with a man. Even kissing one…..<Shudder>"

Gina smirked, "OK, Sweetie. If you say so. Do you have a girl’s name you would want to use when you’re dressing, or just Jeri, like the woman who played Seven of Nine on Star Trek Voyager?"

"I like Brooke," I surprised myself by saying.

"Brooke it is," Gina said. "Now how about showing me a good time? I want my pooper porked by the prettiest tgirl in the state."

I happily obliged her. Three times.

 

 

Chapter Nine -- Pretty as a Picture

For the next few weeks, my life settled into a pattern. An odd pattern, but a pattern. On Wednesdays and weekends, I was "Brooke," Gina’s lesbian girlfriend. I sissied myself up to the max and we exchanged every bodily fluid we could muster. On Tuesdays and Thursdays, I was good old Jerry, swilling the brewskies with my buds. On Mondays, I went to see one of those buds, Mark, as my shrink, in an effort to make sense of what was happening to me. On Fridays, I went to bed early to rest my faculties for the cum-drenched weekend ahead.

During the weekdays, I tried not to let my volcanic private life affect my work. It seemed to be going well there. In my annual evaluation, Brian, my boss, told me I was developing well ahead of schedule and that he expected great things from me. What a good guy! And when I thought about it, kind of cute. Although I really never had those gay thoughts. Cause I’m not gay. At all.

Anyway, Gina wanted me to come to the Friday meetings of the tgirls, where I had met her. I had never been outside dressed, didn’t have the energy and told her so as politely as I could. Gina wasn’t dommy at all. She pushed me a bit to see if I was a tgirl, but no further. She did suggest, however that I have some pictures done by a professional photographer of me in my feminine persona. She said all the girls did it and it’s something I would always treasure. When I asked Mark in therapy if that was a good idea, he said yes…. eagerly. Could he want to see me dressed? Or undressed? Life was so complicated.

I took Gina’s suggestion, made the photography appointment, took a personal day from work, and dressed at my apartment for the first time. I had gotten very good with the make-up. I donned the wig and breast forms. Then I put on my lingerie and a tight pink sweater and black mini, with black stockings and five-inch fuck-me pumps.

I said to myself, "Too hot to handle" would be the caption on the pictures I would take that day. I also brought along some lingerie for part of the shoot if I was up to it. Speaking of up to it, I tucked little Jerry away in a tricky little device that Gina let me borrow. No use showing him off, although looking in the mirror was getting him all hot and bothered.

Very self-consciously, I drove myself to Jim Sanford’s studio. I parked as close as I could, two blocks away, and walked through a gauntlet of construction workers taking their mid-morning break. I was mercilessly sexually harassed. I appeared to ignore it, but I heard every word. It was wonderful! They thought I was a hot babe! I was enormously flattered. I certainly didn’t want to have sex with any of them, but it would be nice if they were there on a break when I walked back. Maybe I did give them an extra wiggle or two and I probably didn’t need to drop my bag and then slowly pick it up.

I entered the studio and Jim Sanford greeted me. He was a pleasant enough man. I paid my deposit and he led me to the area where I would pose. He took around fifty shots of me in my street clothes from all angles. I liked the way he talked to me as if I were a real model. I had high hopes for the results. Then he asked if I wanted to do the lingerie shots. He was very encouraging and professional, so I agreed.

I went into the dressing room and took off my skirt, slip and sweater, changing into a black teddy and a silky peignoir over my stockings, garter belt and heels. When I emerged, Jim gave a very unprofessional low whistle and sported an ungentlemanly bulge in his khakis. I frowned at him and he busied himself with his lights and lenses.

Was the effect I had on those construction workers and Jim typical of how men would react to Brooke? And if so, what did I want to do about it?

The session went well, but Jim was even more solicitous than he had been during the miniskirt session. He acted smitten. He knew I was a man. Why was he acting that way? Was I really too hot to handle?

I changed back into my mini and sweater and was getting ready to leave when Jim grabbed my arm and tried to kiss me. What was wrong with him? At the same time, he reached under my skirt and grabbed my pantied ass. He was snorting sexual heat. He was snorting pain when I kneed his nuts. It wasn’t subtle, but it was effective. As he was writhing on the floor, I tossed a card on his desk and said, "Please send the proofs to this address by Wednesday. Good day."

I was shaken as I clacked the two blocks to my car. No construction workers, darn it, my subconscious said. My conscious was lecturing me on expecting such things to happen if I was going to venture forth babishly.

As I drove off, I analyzed my feelings, as a woman would. I wasn’t entirely put off by Jim’s advances. I felt a little heat too when he grabbed my ass. But he was too crude about it for my tastes. Did this mean I could permit myself to have sex with a man? Even enjoy it? The answer was maybe, versus a definite no a few weeks before. With the right man. Under the right circumstances.

I was so preoccupied that I drove to the grocery store near my house. I needed stuff and was going to go home and become Jerry, then drive back. But I was so agitated, I said the heck with it and decided to test the waters as Brooke.

The lot wasn’t full. I didn’t think I would meet anyone I knew. It was 1:30 p.m. and people I knew were at work.

I didn’t expect a lot of stares in the store, although I did stand out among the housewives in their squeegee man outfits they wore for grocery shopping. I did get some lusty stares from the male staff. I could learn to like that, I thought. Just so they didn’t all take it as license to grab my ass.

I was in the back of the store looking at some wrapped breakfast meats when I dropped several packages of bacon on the floor. A gallant, passing man moved over to help me. Our eyes locked. Sweet mother, it was Brian Callison, my boss. What was he doing here? Now? Like this? Please don’t let him recognize me. Please. Please. Please. Please. Please. Please.

"Jerry?" Brian said. "Is that you?"

I said, "please," didn’t I? I nodded. I was consumed with embarrassment. Maybe I would have come out, but not like this. My life was over. I would lose my job. My name would be put in some book of evil people. This would all be on my permanent record. Despair. Gloom.

"Jerry, you’re beautiful. I’m shocked, but delighted."

And unless my eyesight had gone, Brian had the woodie to prove it. Out of despair. Out of gloom. Curious about the immediate future.

"I knew something was going on with you Jerry. You were preoccupied, but you were better at your job. More sensitive to clients’ needs. But maybe I shouldn’t be calling you Jerry."

"It’s Brooke," were my first intelligible words. "Why aren’t you at work?"

Certainly not the most important question, but a relevant one, nonetheless.

"I had some vacation to burn before the end of the fiscal year. How long have you been dressing? About six weeks would be my guess."

How did he know? "That’s right."

"I know because that was when you changed. And I know because my sister, once my brother, was like you. Only she started at 18. She’s 33 now, married and very happy with two adopted kids. You’re stunningly beautiful, Brooke."

Tell me more, I thought. And he did.

"Your legs are as good as any GG in history. And you haven’t had any hormones or anything. You’re a natural. Have you had lunch yet?"

I said I hadn’t. We abandoned our full shopping carts and went to a lovely French place nearby. We sat and talked for hours and my head was spinning from the attention and all the vin rouge. My brain said to say goodbye, but my lips invited him to my apartment. His lips accepted.

What was I doing? This was a man. And my boss. But my clitty was throbbing every time he smiled.

I didn’t know what I would say when we got to my place. Brian helped me out by covering my mouth with his. I was kissing a man and I was ignited with desire. Jim the photographer tried the same thing and I rearranged his cojones. It’s how you go about it.

Oh, my. Brian was licking my tonsils. My ears were red hot. His right hand was high on my left thigh. Then it was on my pantied ass. I broke free and ran to the bedroom. If I hadn’t, he would have fucked me right there on the floor in the entry way. Brian was in hot pursuit laughing as I giggled.

I pulled off my sweater and removed my mini and slip. Brian drooled. He stripped naked. I drooled. His cock was eight inches and at rigid attention. There was no doubt about it. I was getting fucked that evening. By a man. A nice man. With a big cock. I took comfort in knowing that I wasn’t gay. I was something better.

Brian lifted me in his arms and carried me manfully to my bed. He laid me on my back and covered my body with his. He removed my breast forms and kissed my real nipples. Good golly! There was a thrill.

I had to release my cock from its gaff. Brian understood. I shucked the gaff off with my panties and my clitty gasped for free air. Brian took note of its size, shape and beauty. We lay on our sides, facing each other and gently frigging each other’s equipment. I was very excited and very hard.

Brian asked if I had any lubricant. I blushed and reached in the nightstand drawer. What was he going to do? He wanted to fuck me right away, he said. "If we wait, we’ll be all anxious. Let’s eat our dessert first."

A fine metaphor. I was spooned against Brian. He took some Vaseline on his left index and middle fingers and entered my tight sphincter, gently, but insistently. Tears filled my eyes when he massaged my prostate. At the same time, he put some Vaseline all over his right hand, and he handled my clitty with skill and grace. I was being assaulted on two fronts and I quickly surrendered. I felt a succession of huge pinches in my stomach, then my thighs were on fire and I blew my first load in sexual congress with a man. The real Congress should be so lucky.

I shuddered and squealed and drenched poor Brian’s right hand with girlie cream as he insistently massaged me to a second erection with his left hand.

When he withdrew his fingers, I knew I had reached the border. A knee to Brian’s cojones now, throw out the girlie clothes and I’m back to "normal."

Like hell! Give those eight inches, Baby, and make me scream.

Brian was eager to do so. I felt the head at the portal to paradise. It was bigger than Gina’s. I liked that. He popped it in and groaned. I liked that. It felt like an apple in there. He pushed. I groaned that time. That was about Gina length. He pushed again. Now we were in a whole unexplored territory. The depths of my pooper. Brian began to kiss my neck and tell me how beautiful I was. Let’s see, did I like that? Yes. What exactly is it again that’s bad about sex with a man?

My own clitty was outrageous. It was stretched to all limits with blood and bloody lust. I felt the hot anal love and wondered where this had been all my life. This was pure sexual exhilaration. Brian was grunting toward his own orgasm, but had the kindness to rub my clitty with his cummy hand. It was heavenly.

Brian gasped for breath, then shot a super-sized wad into my almost-virgin pucker. It was hot and juicy. My little willie was in a dither as well and that hot lava in my bowels persuaded my balls to release their treasure yet again into Brian’s skillful hand.

I screamed Brian’s name. He loved it. He said a girl had never done that for him before. And a girl had never let him go in "back there."

"You’re something better," he said.

I knew.

 

 

Chapter Ten – Pretty Wrapping

I won’t say that Brian and I fell in love that night, but it happened over the next few months.

I love sucking his cock. I love the feel of its head’s round topside on my pallet and its angled, sensitive underside on my tongue. I‘ve sucked Brian for hours and hours and swallowed gallons of his cum. He’s been incredibly grateful and very good to me. If diamonds are a girl’s best friends, I have pretty friends all over my apartment.

And Brian learned to love my clitty as well. He’s such a sweetie. He was reluctant to lick my girlie pole at first, but once he got his first taste, I couldn’t pull him off me. <Giggle> He says my girlie cream is the best meal he ever had.

I’m such a girl now. I had to quit my job for two reasons. First, I wanted to be a girl full time, and that’s something you begin somewhere new. Second, I couldn’t be around Brian at work. The bad boy was always trying to maneuver me somewhere he could fuck me or have me suck his cock. I told him we shouldn’t do that when I was dressed in male drag. He said he couldn’t resist me, no matter how I looked. He’s so sweet. Of course I let him have his way with me at work 30 or 40 times and we never got caught. At least I don’t think we did. The urgency and dirtiness made it very intense. And I was wearing my girlie underwear and stockings, so it wasn’t totally gay.

I’ll be getting nice firm titties next week, so I’ll be out of action for a while. Brian said I didn’t need to get them, but watch him dive in when I get the OK for some boyfriend nursing.

I’ve been freelancing out of my home and doing quite well. Wednesdays I still spend with Gina, but the rest of the week is for Brian. I think he’s going to propose to me soon and I know what my answer will be.

Gina is so happy for me. She’s even happier since I introduced her to Mark. They hit it off from minute one and they’ve been having an affair off the Richter Scale.

Poor Tony is the odd man out of our trio, but Gina is introducing him to a girl she knows named Alicia, who has a beautiful face, a giving nature, big titties and a pretty cock and balls. I think that Tony is ready for something better.

Too bad there aren’t enough of us special girls to go around.

 

 

 

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