Broken Hearted Again

by Jennifer White

 

"I can't believe your bad luck with men" said Beth Ann, as she sipped her cappuccino. I was looking down into my cup of latte, stirring it to help it cool off, and thinking about how right she was. Ever since I was a young girl, I had a knack for picking the wrong men. I thought that Allan was going to be 'the one', but he broke it off after we had sex for the first time. Then I thought Richard was it, and he even proposed to me. But during the wedding planning, he broke it off. leaving me with tons of bills (and a now useless wedding dress).

But Jerry had seemed so different. He was kind, he was sensitive, and we took things slowly, since I had such a hard time trusting men. But over time, we grew closer, and things progressed. We got as close as I thought was possible for a man and a woman to be.

"I think my first mistake was when I asked him to move in to my apartment with me" I said to Beth Ann.

"Why did you do that?" she asked.

"I thought he was right for me, and I wanted to be with him all the time."

 

When Jerry moved in, at first, everything was exactly as I had envisioned it. I had a man around the house would fix the leaking faucet, carry the groceries up the stairs, or do the yucky stuff, like cleaning the hair clog out of the drain in the sink. Yes, it was my long hair that was at fault, but it was nice to have a man to do those things for me.

In return, I cooked, I cleaned, I shopped, I did the wash. I bought him new shirts when I was at the store, and bit by bit I was determined to upgrade his wardrobe, and make him slightly more presentable. And it worked. He wore the clothes I bought him, without fighting. And things hummed along perfectly well in our relationship.

 

"So what went wrong at first?" asked Beth Ann, as she took another sip of her hot drink.

"Well, it was little things. At first, he did things around the house for me, without being asked. But over time, he started to do less and less, and I would have to ask him to do it. And after a while more, that didn't work, so I would have to *tell* him to do it. And the resentment between us started to grow."

 

It was a simple thing. I asked him one day if he would fix the kitchen window, which wouldn't stay open. After two weeks, it was still broken.

"Do you need help?" I asked him finally. "Should I call a window place?"

"Nah, I can fix it" he said.

But another week passed, and still nothing was done.

"How's that window coming along?" I asked, trying to prod him.

"I think I need a part. I'll go to the store tomorrow."

I was a little put off at this point!

"How about at half time? You can watch your game, go get the part, and you'll be back before it starts again."

"Not enough time. Plus, I don't want to miss the scores and highlights. I'll do it tomorrow."

"Okay..." I said, knowing that tomorrow would mean several weeks more.

Finally, I reached a point where I was fed up, and I called a window place myself. They came out, fixed it, and charged me sixty dollars.

"What did you do that for?" he asked, insulted that I would dare bring someone else in to help around the house. "You just wasted all that money. It was a five dollar part, and you just paid sixty dollars to fix it!"

"At least its fixed now" I countered, upset that he had waited months, then insulted me when *I* did something about it. I guess that was the start of the downward spiral of our relationship, even though I didn't realize it at the time. That night, he wasn't interested in doing anything in bed. I guess he felt that his manhood was threatened or something, and he retaliated by not getting close to me. I had trouble sleeping. I should have seen what was coming, but I was still too blinded by love.

 

"Did he love you, do you think?" asked Beth Ann.

"I think so" I said, as I twirled my fingers through my long hair. It was an unconscious habit of mine, that I guess goes back to when I was a little girl, and I wished I had curly hair, like Sally Martin in third grade. My friends made fun of me for doing it all the time, but I hardly even noticed.

I stopped doing it, when I noticed that the nail on my left hand ring finger had a chip in the polish. Darn it! I just had them done three days ago. Doing all the work around my house, and often forgetting to put on gloves, I seemed to go through my nail polish way fast. I needed a touch-up every couple of days. Beth Ann on the other hand, always seemed to have perfect nails. I was so jealous of her.

"Did he *say* he loved you?" she said.

"Yes. He said it all the time. And I said it to him. We had no problem in public. He would proudly kiss me in front of all his friends, and tell me he loved me."

"I had one boyfriend who did that" said Beth Ann, "but it always felt like he was trying to show me off, rather than trying to make me feel special."

"I didn't get that vibe from him" I said. "I thought he really did love me, and he wasn't afraid to show it in public."

"So what happened next?"

"Well, over time, things got a little worse. He stopped talking to me."

 

When we had a problem, I tried to confront it, rather than hiding from it, and letting it grow into a larger problem. I had learned from the past that if you let things go, they simmer, and get out of control, then come back to bite you. Better to nip things in the bud, and get over the bump before it grows to become a mountain.

But when I did this, Jerry would just clam up. He wouldn't talk. It would be a one-sided conversation, with me talking to him, and no responses coming back. I was trying to help our relationship, and he was taking it as if I was picking on him or something. Men are so hard to understand!!! Why don't they talk? Why can't they just open up? Don't they have any emotions? I just don't understand them sometimes. Well, actually, most of the time.

So here we were, on the downhill slope of the relationship. I thought we were still going to make things right, and everything would work out. But one night, he didn't show up at my place, and he didn't call. I was worried sick about him. What if he was in a car crash? What if he had been drinking, and fell over in some alley or something? I didn't sleep at all. He finally answered his cell phone at noon, after I had called it about fifty times. He had a lame excuse about not feeling well, and wanting to stay over at his buddies place.

I told him how I had worried about him, and begged him to just come home so we could talk. He was quiet for a while, then hung up the phone.

The next day, when I looked into his eyes, I could tell. He didn't look at me the same way anymore. He had stopped doing all the little things anymore, and I knew that he was just hanging on to our relationship for one thing: he was getting sex every night, and he didn't want that to end.

All my friends tell me I'm very beautiful, and I look like a model. But I don't believe them. I need to lose twenty pounds. My thighs are too fat, and I can't drop that weight that seems to sink right down to my butt. I diet and exercise, but I just can't get into the shape I want to be in. I guess I'm a little insecure about my looks. That's why I had the boob job, to give me the perfect bust I had always dreamed of having. I was too small on top, and that made me feel unattractive. But not anymore. Now I have a perfect pair of 34 D's, and they drive men wild. Even Jerry. When I take off my shirt, I can see him get hard right away.

So he wanted me for just one thing now, well make that two things: sex, and my boobs.

 

"Aw Muriel, that's so awful" said Beth Ann. "And I thought you two were going to work things out."

"I did too" I said, as I waved to the waiter to bring us another round. One advantage of having big boobs, is that waiters jump at the chance to serve you. It was fun to watch them scramble. I don't know if that is mean, but hey, after the way that so many men have treated me, I have a right to make them serve me, don't I?

After the waiter brought us the next round (ahead of the guy who ordered his before us, I noticed), we continued our conversation.

"I just couldn't break up with another boyfriend" I said. "I was just hanging on to him too, waiting for him to leave me. But he wouldn't. I knew we'd never be married. I knew we'd never have love. It was all but over."

"So why didn't you just kick him out?"

"I couldn't. I needed for him to leave me. I'm really bad at telling a man to go, and not come back ever again. When I did that last time, I cried for a week. But when a man leaves me, I get over it much faster. I guess it makes it *his* fault if he leaves me. So I kept waiting."

"But he just hung on."

"Yes. I knew for a fact that it was for the sex. So I decided to do something about that."

"Cut him off?"

"No. Something better. I decided that I would make it tougher and tougher for him to say for the sex. I decided to get kinky with him."

 

I had decided that if I drove him to having really kinky sex, then he would think I was getting weird, and he would take off. So one day I told him I had a fantasy, and I really wanted to do it in bed that night. I made it clear that if we didn't do it my way, we weren't going to do it at all. But that didn't deter him. He was interested.

"What is this fantasy of yours?" he said.

"It goes like this. I walk into the bedroom, and find that my lover is playing with my bra. He picked it up, smelled me on it, and decided to put it on to see how it felt. Just at that moment, I walk in and surprise him. He feels scared from being caught, and feels very meek. I tell him to take off his boxers, and lie on the bed, on his back. I get on top of him, make love to him, and tell him that he's a girl now."

"Wow, that's pretty kinky" he replied.

"Lets try it" I said. Go strip down to your boxers, put my bra on, and I'll be there in a minute."

 

"To my surprise, he agreed. I waited five minutes, and walked in the door. He was staring at himself in the mirror, wearing his boxers, and my bra. He was completely aroused. I ordered him to take off his boxers, and lie on the bed. He looked scared! And I was wet already. So I mounted him, and went at it."

"Wow, that does sound kinky" said Beth Anne.

"It was. I was in total control, and it felt wonderful. I kept telling him he was a girl now, and that he was mine."

"How did he react?"

"He just laid there, unable to speak. When he came inside me, he came hard. He didn't realize it at the time, but he would never go back to 'regular' sex after that."

"Wow."

"Yes" I said, giggling as I took another sip of my drink.

 

I let him take the bra off when we were done, but the next day, we played the same scenario as before, and when we were through, I made him sleep with the bra on all night. I could feel him waking up all the time, and squirming. It must have made him feel quite uncomfortable.

The next day, he said that it had been good, but he was concerned that it wasn't quite as exciting as the first time we had done it. I think this was his way of telling me he didn't want to continue with it. But I wasn't about to back down. So I told him that the only way to keep up the excitement, was to add to the scenario. So I told him to stuff the bra full, before I came into the room.

This time, he had that 'deer in the headlights' look again. And I made him sleep with the bra stuffed full. Since it had worked so well, I decided to add to it, more and more each night. I had him wear a skirt. I had him wear panties. I had him wear a cami top over her stuffed bra. And then I had him put on makeup.

Instead of me telling him he was a girl, I started making *him* say it, as I mounted him, and started pumping him. I told him that his name was 'Tammy' now, and that he needed to tell me he was a girl, and that was his name.

"I'm a girl! My name is Tammy!" he would gasp, as I pumped up and down on him, riding him with his manhood in just the right spot to please me. He always came, and it was always big. I had thought that he would grow tired of this game, and want to get out of the relationship. But instead, it seemed that he *liked* what we were doing. I kept adding to it, making it more and more kinky. But he just ate it up.

 

"So what did you do next?" asked Beth Ann.

"I had to turn up the heat somehow. So I made up a little white lie."

 

I took Jerry aside when he got home from work, and had a little talk with him.

"It's a female thing" I said. "I have to go off of birth control pills for a little while. But I'm not ready to get pregnant. But don't worry, I still want to have lots of sex with you."

"So I have to wear a condom?" he asked.

"No, I know you don't like how they feel."

"Then how can we have sex?"

"Just wait until tonight. Tammy."

 

That night, we did the usual. He got all dressed up. By now, he was wearing a wig, he had a good pair of falsies that made it look like he had real boobs, he wore heavy makeup, and everything. I told him that I had another fantasy, where I catch him dressed up, but this time *he* took control.

"You order me to strip, and lean over the bed" I told him. "Then you pull up your skirt, lubricate yourself with some K-Y, and go at me from behind."

"You mean..." he said.

"Yes. In the butt. That way, you get off, and I don't get pregnant. Make sure you touch my boobs when you're pumping me. Okay?"

"I guess..." he said.

I had a boyfriend before who wanted to do me that way, and I can say that it was just okay. But after having done it once, I could stand it again. He didn't know it at the time, but from then on, my pussy was off limits. He was going to only have access to 'rear entry' from then on. And only when he was dressed as a girl.

 

"So he did it?" said Beth Ann.

"Yes!" I replied. "He did me, and for two weeks, it was the same every night."

"I can't believe he liked it" she said, shaking her head.

"He said I was tighter in back, and it was better for him! Can you believe that!!"

"No" she said. "And that went on for weeks?"

"Yes" I replied. "After a while, he seemed to be very used to it, and he told me he liked it. So I had to turn up the heat again on him."

"How did you do that?"

"I went into an adult store, and bought a strap-on."

"You didn't!"
"Yes. And I told him that night that it was his turn to see how it felt. I told him I wanted to show him how I wanted him to do me. Where he was supposed to touch me, how hard, and all of that."

I told him that before he could do me, I was going to do him. I was very gentle, and very careful. I used a lot of K-Y to make sure it went in easily. And I went at him for a while. I think he was really scared at first, but he got over it. I kept pumping him from behind, telling him that he really was a woman now. And then I let him do me.

I kept this up for a week. Every night, I would do him too. Some nights, he went first. Some nights, I went first. He never realized what I was doing to him, and how I was training him. He thought it was all fun and games in bed. All he knew was that he was getting off on it every night. And he was liking it.

 

"You were training him?" said Beth Ann.

"Yes. I had decided now what to do. Since he wasn't going to get scared off with all the kinky sex, and having me turn him into a girl didn't intimidate him anymore, I had another idea."

"Hold on. He wasn't scared about being called a girl?"

"I did a lot more than that. I made him sleep in a nightie. I made him wear a bra and panties all day. I made him do housework in a dress. I made him wear makeup, and stuff his bra when he was home. But he went along with it all, because he knew it would lead to hot sex in bed when we were done."

"Hot for him. What about you?"

"Well, it didn't get me off. But I was determined to get him to leave me. So I had to do myself. I thought of making him go down on me, but I wanted to cut off all access to my pussy. I didn't want him to get excited by pussies anymore."

"You mean...."

"Yes. I was going to turn him."

 

One night, it was my turn to do him first. I timed it so that when I went for the jar of K-Y, it was empty.

"Uh-oh, no lubricant" I said, after I attached the strap-on.

"But that thing would hurt me if its dry" he said.

"True" I replied. "So get down on your knees, and suck me. Your drool will be the lubricant."

I stuck it out, holding it like a man peeing.

"Now Muriel..." he said.

"Suck me Tammy!" I said harshly. "Now!"

He got down on his knees, and went at it. I really had him now. We would never use K-Y again. It was going to be him and his mouth lubing me up every night, from then on.

"Deeper" I said. "Let it all the way into your mouth."

I started rocking back and forth, thrusting it into him.

"That's a good girl" I said, stroking his hair.

 

"Wow. So he sucked you every night" said Beth Ann, as she put a spoon full of ice cream into her mouth.

"Yes. I got him used to it" I said, as I took my spoon and stole a bite from her dish.

"You naughty girl!" she said.

"But wait. It gets better" I replied.

 

For some unknown reason, men have this thing where being with two chicks at the same time really turns them on. I guess it makes them feel like the king, or the leader of the pack, or something primitive like that. So I told Jerry that we were going to have a special guest that night, a girlfriend of mine who was very much into kinky sex, and that we would have a three-way.

Even though he was going to have to dress up as Tammy, he was into it! Men. They only think about one thing. So he agreed to my plan, without any protest whatsoever! What he didn't realize, was that my friend Paula was a very special girl.

 

I set up the scenario, so that Jerry would be dressed up as Tammy, and he would walk in on Paula, who was putting on makeup. He would do her from behind, as he had been doing to me. As he did her, I touched him all over, patted him on the butt, ran my nails down his back, and whispered in his ear.

When he came inside her, I asked him how it was.

"That was fantastic!" he said. "The best yet."

"I'm glad you think so" I replied. "Now get on your knees to suck."

He did it, just like every night for the past weeks.

"Close your eyes" I said. "I have a surprise for you. A newer more realistic model to suck."

He closed his eyes, and it was Paula's time to show just how special she was. She lifted up her skirt, and I could see her erection in the front. She was a she-male, a woman in every way, except for the fact that she had male genitals. She talked like a girl. She walked like a girl. She felt like a girl. She was attracted to men, like a girl. But she never had the last operation to give her a pussy. She was still a man, but only between her legs.

"Now this one will feel warm to you" I said, as Paula smiled and approached him. "Keep your eyes closed."

And so, there he was, sucking on Paula. I had arranged a signal with her, so that she would wink at me, right when she was about to come.

"Okay, open your eyes" I said, as I stood right behind Paula, so it would sound like my voice was coming from where she was standing.

Jerry opened up his eyes, looked up, and realized that he was actually sucking Paula, not a strap-on that I was wearing. But he didn't yet realize that what he had in his mouth was real. He thought it was some sort of realistic one, as I had said. But that changed when Paula came, and shot her load into his mouth.

"Oh my god!" he said, as he spit it out on the floor, and started wiping him mouth off. "I can't believe you trick me like that!"

"Like what?" I said, innocently.

"I just screwed a man!" he yelled.

"And you told me it was fantastic, and the best ever."

Jerry's face turned bright red. He couldn't deny what he had just said. He had admitted that he liked sex with a man.

"And no matter what you do" said Paula, "you can never take back the fact that you just game me a really good blow job."

"No!" cried Jerry.

"Now sit back and watch" I said, "as Paula goes down me. She can touch my pussy, but you're not allowed in there anymore."

I laid back on the bed, and let Paula put her mouth between my legs, and take care of me. She was really good, and she got me to come several times. I looked up when we were done, and Jerry was nowhere to be seen. I could hear the shower running. He was in there, trying to make himself 'clean' again.

"You can shower all you want" called out Paula, "but you still made love to a man!"

I thanked Paula, and told her to show up again tomorrow night.

 

"Wow! I can't believe you!" said Beth Ann. "You really made him do it with a guy!"

"Well, sort of a guy" I said. "It was just a transition, so I could prepare him for a real man."

"No way!" said Beth Ann, as she ate the cherry from the ice cream dish.

"Way" I replied, smiling.

 

After the initial shock of that first time with Paula, when she showed up the next night, it didn't take too much arm twisting to get him to do it with her again. This time, she did him from behind, and he got to feel what it was like to have someone come inside of you. Then I made him watch as Paula went down on me again.

"God, I wish I had a pussy like yours" she said when we were through.

"Some day you will Paula" I told her.

"How about you Tammy. Do you wish you had a pussy too?" she asked, and that kind of freaked him out. It was one thing to dress up as a girl, but another thing to think about losing his manhood altogether.

 

I had Paula over for about two weeks straight. I wanted to really reinforce one thing in his mind: the only time he got to see pussy was when she was doing me. And since he felt that I was *his*, it made him feel really bad to see that. So I was slowly implanting in his mind: pussy: bad. And for months, he had only gotten off when he was dressed up as a girl.

So I surprised him one day, by making a total change to the scenario. He was dressed as a guy. I had a *real* girlfriend from work come on over. She was pretty, very feminine, and had a high shrill voice, unlike Paula deep husky one. She wore pink, her hair in curls, and was as frilly and girly as you could be.

When she pulled her skirt up , and laid on the bed, she said to him "take me."

"So what happened?" said Beth Ann.

"Nothing!" I replied. "He couldn't get it up! With no props, without being dressed up, his body failed to respond. He hadn't been on top for *so* long. And he hadn't done it in a pussy for a long time either. I manually stimulated him, got him somewhat hard, and made him try. He didn't know it, but we had put a lot of lubricant into her before she went on the bed, so when he did go in, there was very little friction. He pumped for a while, but he couldn't come!"

"Wow" said Beth Ann.

"Yes. It all went perfectly. He failed with a real woman, and a pretty one at that! She pretended to be really hurt and left us. Just as we had arranged."

"How'd you get her to do all that?" asked Beth Ann.

"She hates men. We had been commiserating at lunch one day, and I found out that she was a real man-hater. So she was more than willing to help out, once I told her what the outcome would be."

"So what did you do next?"

"I told him that I was tired of games in the bedroom, I was tired of having others there with us, and we would return to how things were before. Just him and me, with me on my back."

"And what did he do?" asked Beth Ann, sitting nervously on the edge of her seat.

"He left me! He told me he didn't love me anymore, and that he wasn't interested in sex that way anymore."

"You did it! You turned him!"

"Yes. Now he's in a relationship with Paula, although she told me that she'd caught him ogling men lately. I think he's going to go all the way over to the other side."

"Way to go girl!" said Beth Ann, smiling. "You are an inspiration to all of us."

"Thank you" I said, pretending to take a bow.

 

Beth Ann and I left the cafe, and continued shopping. I bought a new pair of shoes, while she found a plaid skirt on sale. We went back to her apartment for a light dinner, after our fun day out.

"Muriel, I have something I want to ask you" she said.

"What is it?" I replied.

"You had a lot of kinky sex with Jerry. So you seem open to new things. There's something I never told you about myself. I like girls. I've never liked being with a boy, ever since I was young. I always wanted just one thing: a woman to be in love with. I was wondering, if you'd be open to giving it a try with me. A relationship."

"You mean...." I started.

"Yes. I'm a lesbian. And I can see in you that you are very tired of men. They break your heart in the end, don't they? You've told me how you have trouble communicating with them. Imagine a partner who you could really talk to. Imagine being with someone who could express their emotions. Imagine a lover who knows your body perfectly well, and who you don't have to teach about how hard to go at you, or where. Imagine a lover who appreciates the same things you do. Someone who will notice when you've redone your nails, or got blond streaks in your hair."

I just had my hair done last week, and Jerry hadn't noticed. But Beth Ann had. I pondered her proposition.

"I've never tried that before" I said. "I've always felt a need in bed for a man. It was hard on me these past months, when I was turning Jerry into a woman. My needs went unfulfilled. I don't know if a woman can give me what I want."

"Will you at least give it a try?" said Beth Ann. "Lets go out on a few dates, and see how it works. And don't worry about in bed. I have something very special, that I think you'll like."

"What's that?" I asked.

"Come with me."

I followed her to the bedroom. She shut the door behind her, and walked over to her dresser. She opened a drawer, and pulled out a black velvet bag. Inside the bag was a dildo, but a very special one. It had a head at *both* ends.

"You should try this" she said. "I think you'll like it."

"I feel wet already" I said.

It was true. I was really turned on. Perhaps all that sex with Jerry when he was dressed up as a woman did something to *me* too. Seeing Beth Ann looking all sexy, and holding that thing in her hand, I was getting wet. We fell into each other's arms, and kissed.

Now I had been kissed a thousand times in my life. But never like this. This wasn't just lips pressing. This wasn't just close contact. This wasn't just sharing warmth between two people. This was *passion*. This was romance. I felt like Scarlet in 'Gone With the Wind' being swept off my feet. But instead of a handsome man taking my breath away, it was a gorgeous woman doing it.

With the men in my life, foreplay was a 'chore' they 'had' to do, to get me ready. With Beth Ann, it was different. It was sweat, delicious pleasure, building up in layer after layer. The anticipation built. The excitement. The passion. I had a thirst for her now, an inner need. She had me more ready that I had ever been in my life.

She pulled out the two headed dildo, and got on her knees. She motioned for me to do the same. She stuck one end into herself, and told me to get close to her. I came so near by, that it was poking me on my pubic hair. She reached down, and expertly guided it into my slit. I felt a jolt of pure pleasure go through me like a lightning bolt.

She reached over, kissed me, and started playing with my nipples, making small gentle circles with her fingertips. Every now and then, she would pinch me, and I would squeal with delight and pleasure. We would rock back and forth, sharing the instrument between our legs, delivering pleasure to each other. We were so close! And we were making each other come.

Suddenly, her head darted down, and started sucking on my left nipple. I thought I was going to explode, the feeling of pleasure was so overwhelming. No man ever made me feel like this. If her kiss had swept me off my feet, this sealed the deal. Even before we were done, I knew that after tonight, I would never go back to a man again.

 

As we lay naked in bed, in each other's arms, I could smell her perfumed body. I had found me true love, the one I would be with for all my life. I had never felt so happy before. I only hoped that Jerry (or Tammy!) wherever he (or she!) was, felt the same. In trying to change him, I had also changed myself. But I was glad. It was all for the better.

Now I was happy. I was the happiest woman in the world.

  

  

  

*********************************************
© 2004 by Jennifer White. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.