Alan's Girl

by Desiree Is Down Here

 

I was jittery. Nervous. Excited. Did I say excited? Excited! I kept walking to the window and looking out, expecting his car to pull in the drive at any time. The nylon of my tights rubbing between my thighs titillated me with every pacing step, and I just kept pacing. Alan would be here soon, and I couldn't wait to open the door for him, and invite him in.

I'd met Alan a year or so ago when we'd met each other in the back parking lot of an adult theater. We'd been instant messaging each other for months regarding our mutual interests, and I'd finally gotten so overwhelmed by the idea that he might be interested in seeing me dressed the way I'd only ever done in private before, that I had agreed to meet him. I wasn't dressed for our meeting, and wasn't sure where it would lead, but I was definitely interested in the possibilities, and so I'd gone. We'd talked, each sitting in our own car, about what turned us on, what we were into, and in the end I'd lost my nerve, said I'd be in touch and left. For a few hours, I was sure I'd made the right decision, but then regret set in and I messaged him that I'd like to meet again, this time with every intention of "doing" something. I never heard back from him.

Then one day, I got to the gym early, and surprise surprise, who was there toweling off, getting ready to leave? Alan. Our eyes met, and he knew who I was, and I knew who he was, but neither of us let on. We both just nodded to each other and went our separate ways. After that I'd occasionally see him in the locker room, or in the gym, but we never talked. Every so often as I was driving home, I'd see him speed past me, and I began to realize that he must live in the same general area. Finally the day came that we exchanged a few words in the locker room, and when I saw those bright blue eyes twinkle in a smile, I knew that this was the man that would make me a woman. I still had reservations, I still was nervous, but I knew that sooner or later I would have to be with him. Submit to him and be his.

Many nights I would lie in my bed, seeing him in my mind the way I did in the locker room. Naked, tall, and lean, and imagine sinking to my knees in front of him. Stretching my tongue out to caress the underside of the tip of his cock. Press my lips against it, and slowly push my head forward, lips stretching to glide over the swelling purple mushroom tip until it filled my mouth and my lips closed over the head of it. I would stroke myself, and imagine the velvety softness of the skin over his hardness. The way I wanted to put my hand around the base of his shaft and go down on him until my lips touched my fingers, and his length filled my mouth, my tongue gliding along the underside. I wondered what it would be like to feel him swell just before coming, what would his cum taste like, and would he pull out and cum on my face, or would I take him in as deeply as possible and feel it against the back of my throat?

I would fantasize about him taking me from behind, bending me over, penetrating me with one finger, then two, assuring himself that I was lubricated and ready for him, then the sudden thrust of his body against mine, and my pressing back to meet him and be filled by him.

I spent hours of nights trying to drift to sleep, and unable because the lust inside me for this man was so intense and so vivid.

One night as I lay there, something in my mind snapped. I decided. I could wait no longer. I had to know what it would be like to be possessed by him. To submit my body to his and to attempt to give him the pleasure that giving him would give me. And so I began to plan.

The following day, I visited a local thrift store. I found a thigh-length gray skirt that fit snugly around my waist and hips, restricting the length of my steps, but made of a material that had some stretch to it. I also found a green plaid skirt similar to a school-girl skirt that fell just to my knees. I looked for shoes, but found none that would fit me, hardly surprising. At the next thrift store I visited, I was fortunate to find a bra that fit nicely and left just enough room to stuff in a way that would look fairly realistic. I also found a pair of two-inch black heels, and a pair of Mary Jane's that I knew on first site I had to have. I quickly collected my things and headed to my next stop, the local drug store. Hardly able to contain my excitement, I ran in and picked up some perfume, two pairs of tights, one white, one black, some personal lubricant, a box of condoms, an enema, and a package of liquid suppositories. I also grabbed a pair of hoop earrings. I made one last stop at an adult novelty store and picked up an eight inch dong with "balls" at the base, and a mid-size butt plug.

When I got home, I quickly stripped. I laid down on my side on the floor, and inserted the liquid suppository nozzle, squeezing the bulb until I was sure I'd emptied it's entire contents into myself. I laid there for a few moments, breathing steadily and gently as I felt it's effects begin to take place. Shortly after emptying myself, I showered. When I got out I powdered and perfumed myself, put in my earrings, pulled on the black tights, and the gray skirt. I filled two water balloons with warm water, fastened my bra, and placed the balloons in the cups. It took me a couple of attempts to get the right volume of water, but once I did, I pulled a black turtleneck shirt on, made some minor adjustments, and stood back to see how I'd done. It wasn't half bad. While I could never actually pass for a woman up close, if seen from a distance or from behind, I might. I slipped into the heels and began practicing walking. The tightness of the skirt and the obvious protrusion of my erection were a problem, but at the moment I didn't worry about it. As my excitement built, I took off the tights, pulled up the skirt, and got out the dildo.

I stroked myself a few times, took a deep breath and lay back on the bed. I closed my eyes and began to picture in my mind that Alan was in the room. I could imagine him sitting in the chair beside the bed, asking me if was ready for him yet. I whispered to him, "no, not yet. Patience darling, please, have patience with me." I spread my legs, applied some lubricant to my fingertips, and reached down between my legs. Down, past my penis, past my testicles, past the sensitive area behind them, down to the opening there, and pressed my fingertips against it. I rubbed it in soft circles, then more firmly. I applied more lubricant to my fingertips, and pressed my fingers further in, through the clenching muscles, rubbing them, relaxing them, feeling them loosen to the intrusion, feeling myself opening.

I reached for the dong, licked the tip of it, imagining it was him, taking the end of it into my mouth, pushing it back towards my throat, feeling it press against my tonsils, then pulling it out. I used my lubricated fingers to lubricate the end of it's thickness. Put my hand around the shaft. It was easily twice as thick as my own penis. Twice as thick and several inches longer. I wondered how much of it I would be able to take inside of myself. Then, thinking of my future lover, knowing that if I could take all of this I would be certain of pleasing him, I pressed it against my anus. Felt the tip of it, so much thicker feeling down there. Pressed it against my lubricated opening. My muscles tightened as they felt the attempted intrusion. I pushed harder and felt a sharp pain. I reached down with my fingers again and rubbed gently at the opening. My fingers would slide in, but my muscles would clamp against them and would not relax. Taking a deep breath, I realized that I would have to try another way.

With the skirt still bunched up around my waist, I got up on my knees on the bed, set the dong between my legs, and slowly eased my ass down until the tip was pressed once again at my hole. I reached back with my fingers and smeared a little extra lubrication on the shaft and tip of it and on myself, then settled back until the weight of my body was pressing down against it and forcing it up into me. I gyrated against it, holding the shaft between my legs with my hand so that it remained still, and little by little worked my way down on it.

As the bulb of the head began to enter me, I could feel an incredibly painful stretching. I stopped pressing down, and let my muscles become accustomed to the size of the dong. After a moment, I eased back up off of it, applied a little more lubrication, and slid back down as far as I could go. The pain was intense and brought tears to my eyes. I have often read stories of people being penetrated the first time, and every time they describe the sensation as at first sharply painful, then gradually becoming just as intensely pleasurable. At the moment the pain for me was the pleasure. In my mind I was being penetrated by Alan, and in wanting to please him, I was willing to suffer a momentary pain for the pleasure I would soon give. I slid back down the dong feeling my ass stretch around the widest part of it, then felt the head slide into me. As it popped through the opening, I gasped. Feeling it inside of me, causing me to feel so full, my body began to flush with warmth. I paused for just a moment, then pushed down harder and felt the tip penetrate further into my body, and the shaft glide through the muscles at my opening. It felt so wonderful, so complete, so filling. I felt the ache of the pain subsiding as I slid lower. I began to feel some discomfort after only taking in half of the eight inches, so I slid back up, holding the balls at the base of the dong to pull it out of me. As I got to the top of it I realized that I would have to feel that wide stretching in the opposite direction if I were to pull completely off of it.

I was a little afraid of that pain and was enjoying the filling sensation of being penetrated so much that I simply added some lubrication to the shaft and slid back down again, this time managing to take in about five inches. It felt so good that I rolled over onto my back again, reached between my legs, and began to work the shaft in and out, feeling the large head as it moved deep inside my body. Soon my erection was throbbing and even though I'd promised myself that I wasn't going to masturbate, I couldn't help reaching down and stroking gently. With each stroke the intensity of the feelings in my ass increased and I moved the dong faster and faster.

Within moments I was cumming intensely, the stickiness shooting up through my fingers and onto my black turtleneck. My anal muscles were clenching in spasms and pulling the rubber penis deeper into me. In the few minutes that it took to regain my breath, I put my cum covered fingers to my face and smelled the semen that coated them. I've never been turned on by the idea of my own cum, but for some reason I've always wanted to know what it would be like to feel a penis ejaculating in my mouth. I thought to myself, "well, you'd better get comfortable with it", so I flicked my tongue out and touched the tip of it to one of my fingers. The taste was not all that bad, so I took a deep breath, opened my mouth, stuck a finger in and wrapped my tongue around it and pulled it out. I now had my first real taste of cum. I swished it around in my mouth, gradually getting used to it, then swallowed. I felt a strange sense of pride. Here I lay, legs spread like a woman, skirt bunched around my waist, skewered by an impossibly large (even if it was fake) penis, tongue coated with cum. With a little more practice and stretching, I'd be ready for Alan.

I slowly began to pull the dong out, and quickly remembered that the pain of removing it was going to be just as bad if not worse than the pain of the original penetration. I decided to make it quick, so I rolled over on my knees slid it out as far as possible then squinched my eyes closed, relaxed as much as possible and pulled. It popped out with a sharp pain, then slowly the pain subsided and I lay there thinking how much better it would be with a real man whose penis softened after cumming. I reached down and traced the sore edges of my stretched hole with my fingertips, then reached for the butt plug and inserted it quickly. It was not quite as wide as the dong and it entered easily, my muscles tightening behind it and pulling it in. I wanted to make sure that I stayed stretched so I planned to leave it in from then on.

I got up, took off the skirt, threw the shirt in the hamper, took off the bra, and turned out the lights. It had been a long and exciting evening.

The next day my ass was incredibly sore, and it took a couple of days of wearing the butt plug for the soreness to gradually go away. I was getting in the habit of wearing one of my outfits every day after I got home from work, and began to feel very comfortable in them. Each night I would lube up the dong and go down on it, each night getting closer to the base. I would try and sit down on it letting my weight push me lower and lower. I would feel the bulbous head of it pressing up into my body stretching my insides. I had chatted briefly with Alan a couple of times at the gym, and was feeling excited to share my secret with him. On a Wednesday, I slipped him my new screen-name, suggested that we IM later that evening, and left the gym in a cheerful mood.

That night, I got home, used a suppository, lubed up and sat next to the computer, slowly working the dong into me. Just as I was doing this, I got a message from someone saying "hi, this is Alan". I slid up off of the dong, and typed in "hi! I was hoping you'd message!"

We chatted about the day and other little nonsense for a few minutes, then I messaged, "Alan, you may remember that the last time we met I was a little insecure about getting more familiar. Since I saw you in the gym recently though, I've become convinced that I want to be with you. I've been purchasing things to wear, and getting ready for you, so if you would like to be a little late to work on Friday, I'll be home waiting for you."

His reply was short and sweet, "directions?"

I gave him directions, then messaged one more thing, "Alan, is there anything in particular that you would like to request of me?" He replied asking what clothing I had. I told him and he told me what he wanted me to wear for him. As I signed off, my hands were trembling. There was no turning back now. He new where I lived, he knew my name, he could find out just about anything about me from people at the gym. I was definitely in his power now. He was in charge from now on, and I was shaking with the excitement of it. I was overcome with anticipation!

As I thought about it and fantasized about the fantasies I would play out on Friday, I began to slide up and down on the dong. I was really enjoying it, and the incredible feeling in my ass began to build and build. I began to sense that I was about to cum for the first time without touching myself at all. I was going to get off simply by the penetration occurring in my anus! I was going to get off by being penetrated, just like a woman, Alan's woman.

I kept riding up and down getting more and more excited imagining myself bent over, being impaled by him. Imagining the feeling of his hips slapping up against my cheeks. The building friction peaked and my body was shaking with the intensity of the orgasm, spurt after spurt of cum flying from my dick. I was catching as many as possible with my hand, and as my orgasm subsided, I let my body slide down on the dong until I was sitting on the balls at the base of it, completely impaled, feeling them pressing into my body, just behind my own balls. In my mind I imagined the way this would feel with Alan behind me, his balls and the weight of his body pressed against me. Breathing deeply, I reached my hand to my face and began licking the cum off of it, sucking it into my mouth and down my throat. I didn't stop until I had cleaned my hand completely. Sitting on the fake penis, it's balls were rubbing that sensitive area behind my balls and getting me excited again. I started to grind down on it, sliding back and forth over the base, feeling it rub me, the thick shaft of the dong deep inside me stroking back and forth and in and out with each motion.

The next day Alan and I made eye contact in the locker room, and I couldn't help looking at his penis. Both of us started to get a little hard, and quickly turned away from each other, but not before he gave me one of those wide knowing smiles. I had to sit down quickly and try desperately to think of something else before my erection became evident to everyone in the room. I threw a towel over my lap, and pretended to get things out of my bag. As he left the locker room, he gave me a quick pat on the shoulder and slipped out the door, saying "I'll see you tomorrow."

When I got home that evening, I quickly stripped and got into the shower. I washed carefully, and after getting out, took a Xanax to calm my excitement and help me sleep. First thing in the morning, I was up again, gave myself an enema, lubricated the dong and slid down on it, riding it to my first orgasm of the day. I now felt clean, stretched and lubricated, and set about shaving all my facial hair, putting in my earrings, putting a little makeup on, as well as some lipstick. Then I put on the clothing that he had requested. I pulled on my black tights, my plaid skirt, my bra, and my turtleneck shirt. I put on the Mary Jane's, and started making sure the place was straightened up. As I did I continually paced the room, tidying one thing, then the next, each time going back to the window to see if he was coming down the street. Finally I saw him pull in the drive, and my knees got week, starting shaking, and the butterflies in my stomach went crazy! If I'd had any reservations, it was now definitely too late! I went to the door, and pulled it open after his first knock.

The look in his eyes when he came in calmed me. He looked as if this was absolutely normal. I smiled nervously, shut the door, and said in a quavering voice, "hello Alan". I'm sure he saw the deer-in-the-headlights look in my eyes, because he stepped close to me, leaned down, grabbed the back of my head, and pressed his lips to mine, opening my lips and pressing his tongue into my mouth. I practically fell down right then! I had never been kissed by a man before, and this kiss set the whole tone of what was to come. He pulled back and smiled. this smile may have been the same, but I was suddenly seeing things in a different light. I was his to command. I took a deep breath, invited him in, and offered him the recliner in my living room. I asked if he would like a drink, and he replied "yes, water please". as I went to get it for him, I looked back and saw his eyes roaming up and down my body. I peeked and saw that there was the hint of an erection in his crotch, but couldn't tell for sure as he was now seated.

Returning with his glass of water, I brought it to him and placed it on the coffee table beside his chair. He looked up at me and said, "what shall I call you?" "I don't know," I replied, "I've considered it, but never come up with a satisfactory name." "I think we will call you Desiree, because you obviously have wanted this for a while." "Oh, that's pretty! I will be happy to be called that," I said. "Come stand here in front of me," he commanded, and I stood, breathing heavily in front of him. He leaned forward, and rubbed my tights from the ankles up the outside of my hips, then around, squeezing my cheeks, and then between my legs reaching up to feel the base of the buttplug, gently pushing against it so that it moved inside of me. I gasped a little, and was rewarded with a smile.

He stood up, "let me take my clothes off, so that I can get a little more relaxed." and as he removed each article of clothing, I took it from him, folded it and put it on the sofa. I had seen him naked many times in the locker room, but the knowledge of what it meant this time had me breathing heavily, my erection obvious as it pushed the front of my skirt up.

As soon as he was completely undressed, I was unable to help myself. I had been watching as he freed his erection and dropped his boxers, and as it bobbed free, and stood out in front of him. I reached out and as gently as possible, wrapped my fingers around it, trapping it in my fist. I looked up into his eyes, and he leaned down again, pulled my body to his tightly, pressing that hard erection into my belly and kissed me fully on the lips, piercing my mouth with his tongue, probing my mouth until I went limp. I reached my arms around his nakedness and squeezed back, opened my mouth to him, caressed his tongue with mine until he broke the kiss. His hands went to the top of my head, and he pressed lightly down, pushing me down. I realized what he wanted, and bent my knees willingly, dropping to the floor in front of him until I could smell his sex, smell the musk from his balls, and the purple shining head of his cock, larger than I had ever even imagined, was pressed against my cheek. His hands were on the back of my head now, and I looked up to see his blue eyes, large pools of seriousness full of desire, guiding me to him.

I pulled back and looked at the penis in front of me, saw it jerking slightly with each heartbeat, full and thick and hard, pointed right at my face. I leaned forward, and stuck my tongue out, gently licking the slit with it's slight drip of precome. I tasted it and smelled it, leaned forward further and licked, starting with the back of my tongue and sliding it back into my mouth with a line of his precome to the tip. Then I leaned in again, pursed my lips like I was kissing it, and felt his hands press more firmly on the back of my head. I leaned in, my lips opening with gentle suction, until they had passed over the head, just like my fantasies, and were snug around the corona. Then I leaned further again feeling the veins of the shaft under my lips as I took more of him in, feeling the head fill my mouth as it pressed further back. I gagged slightly, and pulled back, opening my lips to get a little air in, then reached my hands behind him to hold his butt for support, as well as to pull him in to me. I began to rock back and forth on my knees. Breathing carefully in through my nose on each forward dip, and out as I leaned back. He was larger than I had imagined, and my mouth was stretched widely. I could open my lips a little further, but just barely. Even opening my throat and taking as much of him in as I could, I could only get about half of his length inside me without gagging. I was sure that with practice I could learn to deep-throat him but at the moment, I grabbed the base of his cock with my right hand, lubricated the shaft with a mixture of the saliva and precome from my mouth, and stroked in coordination as he slid in and out of my mouth.

Alan was obviously enjoying this too, since he kept pulling a little more firmly on the back of my head with each stroke as well. His thigh muscles were taut and his breathing had gotten a little faster. I felt his cock get a little harder in my mouth, and began to consider whether or not I was really ready to have him cum in my mouth. I started to pull back off of him, hoping that as least this first time I would just let him cum on my face or even in a tissue I had on the coffee table nearby. He relaxed his hold on my head, and I pulled off and reached for a tissue. As soon as he saw what I was doing, he looked down at me and said in a slight growl, "no way Desiree, put your mouth back on me, I want to see you swallow everything I have to give you," and with that he pulled my head back down towards him. I thought to myself, "this is not the way you wanted this, but you better do what he tells you now," so I opened my lips, and he pushed his hips up and pulled my head down. The head of his cock was even more swollen now, and grabbing one of my ears and the back of my head, he began to push me back and pull me forward. More forcefully each time as I tried to get back into the rhythm I had established moments before, then he slowed to a complete stop, pulled me down firmly and I felt his cock start to twitch. First just the head was spasming, then the shaft seemed to swell and shrink and swell and shrink and I felt the salty thick heat of his sperm against the back of my tonsils. It was so far back in my mouth that I was too busy focusing on breathing to really pay attention to the fact that it was dripping down my throat. I could barely taste it, and with each breath I'd take a swallow to clear my throat and I could feel it go down. As his breathing slowed, he pulled back a little bit, and I held the softening head of his cock in my mouth. He was still oozing small spurts of cum, and I let them coat my tongue as I twirled it around him. His fingers were stroking my ear and my head and I looked up at him to see his head tilted back. He looked down at me as I did, and smiled. He said, "Open your mouth before you swallow and show me your tongue." I opened, letting his dick fall out and stuck my tongue out at him. He reached down and stuck his finger in my mouth and ordered, "now suck on my finger and swallow all of that." I looked directly into his eyes, applied suction to his finger, licking and sucking on it with my tongue, and swallowed all the cum left in my mouth as I did.

"That was good, Desiree," he sighed. "I'm impressed. Did you enjoy that?"

"I did"

"Was it what you imagined it would be?"

"Very much, my heart is still pounding. I'm going to have that taste in my mouth reminding me of you for the rest of the day," I smiled up at him. "I can't wait to do it again."

 

Alan slumped down into the recliner, and laid his head back. As I sat at his feet staring at his limp penis, I rubbed my tongue around the inside of my mouth tasting the coating of cum on the roof of my mouth and my gums. I couldn't help myself and got up on my knees crawling in between his legs. I leaned down and took his cock in my mouth again, and sucked gently on it, enjoying the ability to take it all in. I sucked it in and lowered my face down in his crotch until my tongue was pressed into his pubic hair and my chin nestled against his balls. I lapped with my tongue along the soft skin on the underside of his cock. Then I pulled back up off of it, let it fall out of my mouth, and using two hands lifted his leg over the arm of the chair. I lowered my head to his balls and lifting them with my hand put one, then both into my mouth. I held them there as gently as I could, then began to undulate my tongue and move them around it. I heard him gasp, and felt a swelling as his cock began to harden again. It rose against my cheek, and I could feel it get swollen.

He pushed on my head and pushed me back away from him. I let his ball fall out of my mouth, and sat back on my haunches in front of him. "Stand up." I stood in front of him, my skirt tented out due to my throbbing erection. He reached out turned me around, his hands on my waist. Lifting the back of my skirt, his hands explored my ass. He grabbed the inside of my thigh firmly, and reached up to the base of the butt plug. He felt the base of it through my tights, and manipulated the end of it pushing it up into me, then wiggling it side to side. He stood up behind me, pressed his body against me, his erection first poking against the small of my back, then sliding up until I could feel the hard length of it firm between us. He leaned down and whispered in a seductive half growl, half moan, "Desiree, you had best get us some lube and a pair of scissors," then pushed me forward with a pat on the bottom.

My head was whirling. Scissors? I understood the lube, but scissors. I trusted Alan, but as I fumbled through a drawer I was still trying to figure it out. I came into the living room to find Alan standing there lightly stroking himself. "you have a dildo somewhere?" he asked. I was shaking slightly, and so nervous that I didn't trust myself to speak, so I nodded. "Go get it."

When I came back with my dong Alan took it from me and let out a low whistle. "Can you take this whole thing?" As he put it next to his own penis, comparing the two, I realized how big his actually was. It was only about a half inch shorter than the dong, and barely thinner. I swallowed, and tried to calm myself, "yes, when it's got plenty of lube on it I can take the whole thing. I usually sit on it, and can sit all the way down to the base." He got a sly smile on his face and said, "I believe this is going to be very fun. Have you ever been fucked before?" "no, I can tell you haven't. Your knees are shaking baby." "don't worry, I'll be gentle, and if you can take this whole thing I think you will enjoy this quite a bit." I looked up at him and nervously licked my lips. I tried to smile, and as I did he turned me away from him. "get down on your knees Desiree." I sank to my knees. "now bend over and put your elbows on the ground."

I did as he ordered, and felt him push my legs apart and kneel between them. He pushed the back of my skirt up over my ass and over my back, so that now I was covered only by the thin nylon of my tights. I heard him open and close the scissors then felt him grab at the material under the butt plug. I heard the scissors cutting fabric and realized that he had just cut a hole in my tights, right behind my anus. His fingers closed around the base of the butt plug and my ass involuntarily clenched. He reached his right hand around my thigh and rubbed down to my knee on the ground, then back up to my hip. "Relax Desiree, I'm going to pull this out of you" which he did even as he said so. I closed my eyes trying to relax, and felt it slide out of me.

Alan was obviously very turned on because his breathing behind me was getting rougher by the minute. I heard him squeezing out some lube, and felt the chill of it as he pressed it against my hole. He rubbed two fingers against it through the hole in my tights and then slipped first one, then two into me. As I rested my head on my folded arms, feeling very vulnerable and exposed with my ass in the air, I allowed myself to concentrate on the feeling of him penetrating me with his fingers. I was so used to lubricating myself that the sensation of being touched by someone else made the feeling seem brand new. He was totally in control. His fingers touched every bit of me, caressing and massaging the muscles and reaching inside to curl around and rub them from the inside as well. I was really beginning to enjoy this and starting to sway back to meet his hand when I felt his fingers pull away.

I realized what was coming, and kept my eyes closed and my head down, trying to stay relaxed even as my body tightened all over with anticipation. I felt him shift behind me, and then felt his hands on the side of each of my hips. There was a slight pressure against me, and I felt the head of his cock sliding up and down in little strokes. It was very slick as he pressed against me and he slid it up and down between my cheeks. Then slowly he stroked all the way up between them, his hardness going up against my skin, under the material of the tights, until it's tip was on the small of my back and the entire length was nestled between my ass cheeks, his balls pressed against me.

He leaned over my back, took the top of my ear between his lips then his teeth, and whispered in a hot breath, "are you ready?" I moaned and wiggled my ass a little, and said "yes Alan, I want to be yours." He kept the top of my ear between his teeth, slid his cock slowly down my ass until just the tip was firmly at my hole, then bit a little harder and started to push forward. He didn't thrust all the way in the way I'd expected. He pushed slowly. I could feel him entering me little by little, and could feel myself stretching around the plum-sized head. His cock was incredibly hot, and the heat as it inched into me made me want to buck back against him and take more in.

There was no pain thanks to the practice with the dong, and as his head passed the entrance, I felt intense pleasure rolling in waves through my whole body. His breath in my ear, and the slight sharp pain of his bite only added to the pleasure I was feeling, and slowly he pushed against me, filling my body with his hardness. I could feel the throbbing of his cock in my ass and my muscles began to clench and relax, suddenly beyond my control. He got about half way in, and I felt him begin to pull back. He let go of my ear, licking it as he did. He straightened up behind me, pulled out until just the tip was inside of me, then pushed forward more firmly. I felt myself stretching as he went further and further into me, then I felt his abdomen against my ass, and he was all the way in! He gripped my hips firmly, pulled me hard against him, his dick pushing as far as it could inside me. He held me there for a moment breathing hard. I could feel every bit of him inside me. The walls of my ass were spasming along the length of his cock as it swelled and throbbed.

I could have stayed like that all day. His weight had pressed me forward pushing me down into the carpet on my elbows. My skirt was hiked up around my waist, and my tights were a smooth and comforting second skin around my legs. Alan's legs were pressed against the back of my thighs and his stomach was pressed tightly against me. My ear was stinging slightly from his bite, and damp from where he had licked me. His entire length was inside me, and when I put my head down and looked down between my legs I could see his balls swinging slightly and bumping against me. It took me a moment to realize it, but Alan was making a low noise inside his chest and it got a bit louder as he began to slide back away and out of me. The difference between the real cock inside of me, and the dong I had been playing with during the week were like night and day. And the weight of Alan's body hot and hard against mine made comparison impossible.

As he slid out, I relaxed my muscles. When he began to thrust in again, I tightened them. As he began to stroke more steadily, I rocked back and forth trying to match his rhythm. He had used plenty of lubricant, and his cock glided smoothly in and out of me, the friction building with each stroke. In almost no time Alan was penetrating me more rapidly, and I was unable to keep contracting my muscles in time with him. The heat building between us was growing, and he was no longer entering me gently. His stroke had angled and caused the head of his cock to feel like it had swelled inside. This feeling quickly intensified, and I began to gasp for breath as his hips slapped harder and harder against my nylon covered ass, and his weight pushed me harder and harder against the floor. My elbows began to get raw, and soon my chest as well as my face were pressed into the carpet. Only my ass remained reared in the air, and he continued to skewer it relentlessly. All of a sudden, he pulled on my hips again, pulling me hard against him, then fell forward over me. He held himself up over me, and hung his head down, taking my ear between his lips again, this time nibbling it as his ragged breathing slowed. I could feel his cock twitching in my ass, then I collapsed flat on the floor and he collapsed on top of me. I lay there feeling his weight on my back, and his cock slowly softening inside me.

We lay there quietly for a few minutes as our heartbeats slowed and our breathing returned to normal. I felt a soreness between my legs as Alan pulled out of me and some of his cum dribbled out of me as well. It dripped down under my tights mingling with my sweat and onto my balls. I was too tired to move and could only roll over onto my back and watch as Alan stood up. "Where is your bathroom?" he asked, and I pointed down the hall. My eyes wandered up and down his muscular back and butt as he walked away from me. I closed my eyes then and concentrated on the way my body was feeling. I was warm all over, and felt a satisfying glow suffusing me. The soreness of my ass and the residual taste of cum in my mouth gave me a deeply intense delight. Even though I had not cum, I felt the way I do after a strong orgasm. I was very relaxed and comfortable and my body felt though I had just worked out in the gym.

Alan returned and began to get dressed. "I have to go to work now, but I plan on calling you this weekend and I expect you to make yourself available to me. You look very cute laying there all worn out, and I certainly plan on making you look even more so soon." When he finished dressing he kneeled down, and leaned in to plant a lingering kiss on my lips. He moved between my legs and lifted first one, then the other up off the floor and onto his shoulders. Picking up the dong, he leaned forward pushing my knees to my chest and put the tip of it at my lips. Understanding what he wanted, I opened my mouth around it and he pushed it in. I opened as wide as I could and he continued to push until it could go no further. "Get this wet." He commanded, and I licked around it coating it with as much saliva as I could. He removed it from my mouth, then pressed it between my legs and worked it into me. With my legs on his shoulders and as stretched as I was, it slid all the way in easily, and Alan pushed until the base was firm against me and the balls were snug against the skin behind my own balls. Letting my legs down Alan said, "I want you to keep that inside you until I call you. Don't move. Stay right here. I'll call you from work, and you can let it out then, but not until. Do you understand Desiree?" I nodded and replied, "Yes Alan. I'll wait."

"Alright then. I'll need the number." He scribbled it down as I told it to him, then folded the paper and put it in his shirt pocket. He leaned down over me once more to plant a quick kiss then got up and walked out the door.

I continued to lie there on the floor, listening as his car started and pulled out the drive. I drifted off into a daydream while the dong filled my body the way he had only minutes before. As I replayed the past hours in my mind, I began to fantasize about all the ways I would service my new man in the future. I stuck my finger in my mouth and imagined it was his. In my mind I heard him telling me to swallow, and I sucked hard on my finger as I did. I reached down and pulled the dong deeper into me remembering the way it had felt as he entered me for the first time and filled me.

I must have drifted off to sleep because the ringing of the phone woke me suddenly. As I grabbed for it, I reached down between my legs to make sure the dong was still as far inside of me as I could get it. Alan's voice reached through the phone. "Desiree, did you obey me?" "Yes Alan, I still have it inside me." "Good girl. Now I want you to sit flat on the floor with your legs straight out in front of you." I adjusted myself and said, "okay. I'm sitting the way you asked." "Now tell me what you look like." "I'm sitting here in the living room pretty much where you left me. I've got my legs straight out in front of me, and my skirt is spread on the ground around me. Most of my weight is resting on the base of this dong, and that is forcing it tight against me and up into me."

"Good girl. I'm going to hang up now. You may remove that when you want. However, we are going to lay some ground rules for the future. From now on whenever you are home, I want you to be dressed up pretty as if you expected me to arrive at any time. Whenever you answer the phone and hear my voice you are to wait for my instructions. If you do not please me completely, I will make sure all of your co-workers find out about you. Do you understand?" "Yes Alan, I do." "Okay then, I will talk with you later. Have a good afternoon Desiree." "Bye Alan." I replied, and hung up the phone, my heart beating hard.

I hadn't bargained for this! I had wanted to be with him, but I hadn't planned on a life of servitude. Unfortunately, he now knew much too much about me and could make my life miserable if I didn't obey him. I was stuck. As I sat there stunned, I began to wiggle back and forth on the base of the dong. Feeling it move inside me, I started moving faster and faster. It was as if I was trying to loosen the knot of anxiety his call had left inside me. I folded my knees up under me and started to ride up and down. I would lift myself up until only the tip was inside me, then drop my weight down on top of it feeling it penetrate deep into my body. I kept this up, avoiding touching my penis, sure that I could bring myself to orgasm without stroking it. I kept going and going, speeding up and slowing down, and still could not get off. As I got tired I began to be overwhelmed with frustration and exhaustion. All of the feelings crashed in on me and I rolled over on my side and began to cry. Sobs wracked my body and I wrapped my arms around myself and cried myself to sleep.

When I woke up later that afternoon I had a better perspective on the whole situation. I realized that I had really enjoyed my encounter with Alan and was looking forward to seeing him again already. I still felt some anxiety and nervousness about the situation, but decided to put the best face on it and see where things went. I was finishing a shower when I heard the phone ring. I quickly toweled off and ran to pick it up. "Hello?" "Hello Desiree." "Hi Alan" I said shyly, and remembering his instructions I sat down quickly. "Desiree, I've been hard all day thinking about you. I'm leaving work early, and am going to come by there." "Okay Alan, I'll be ready for you." "Good girl, I'll be there in about twenty minutes." He hung up the phone.

He'd been thinking about me? All day? And been hard the whole time? How exciting! I hurried to get ready for him. I put clean sheets on my bed, gave myself an enema, put on some makeup and pulled on my white tights and my green plaid skirt. Because the heels didn't match, I put the Mary Janes back on. I was fastening my bra when I heard the doorbell ring. I didn't want to keep Alan waiting, so I ran to the door and opened it without putting a shirt on. He had a package in his hands, and came in quickly and closed the door behind him with a big grin on his face. "I thought you were going to get ready for me?" "Alan I was trying, but…" he put a finger to my lips to stop me and said, "I know you didn't have very long Desiree, but in the future please try to be ready for me." As he said this he put the package on the floor, reached out and began fondling my "breasts" through the bra. He reached around behind me and undid the hooks and let the bra fall to the ground. He picked his bag back up and said, "let's go to the bedroom." I took his hand and led him to my room. He kicked his shoes off and began to undress.

"Get me the scissors again Desiree." I went to get them for him and when I came back in the room, he bent me over and cut a hole in my white tights. "Did you get off after I left this afternoon?" "No sir, I have not yet." "Good. Put these scissors back and bring me a glass of water please." I brought him a glass of water and handed it to him. "Now I want you to be relaxed before we get started, so please go into the next room and masturbate. When you cum, I want you to cum in this glass." And with that he finished the water and handed me the cup.

I went into the next room and began stroking myself. It took me a moment to get hard and as I was feverishly trying to cum I heard Alan call from the next room, "what's taking you so long? I expect you do this all the time, hurry up, I'm getting impatient!" Hearing him I began to think about the way he had fucked me earlier in the day and that pushed me over the edge. I came hard, holding the glass in front of me and watching my cum splash against the edges, then coat them as it pooled in the bottom. I pulled my tights back up over my softening penis and straightened my skirt as I walked back into the bedroom. Alan took the glass from me and set it on the nightstand. He was lying on my bed, and quickly swung his legs over the edge so that he was sitting on it facing me where I stood in front of him. His erection was pointing directly up at me and I stood there staring down at it, fascinated.

The head was large and purple. The skin was stretched tightly over it's swelling and looked shiny. There was precum oozing from it and dripping down to the underside of the head. His shaft was paler, wide and pulsing with veins just under the surface. I looked up at him and he nodded. I sank down to my knees and inched forward until it was only a hair's breath from my face. I had stuck my tongue out and was lapping at the underside of the head licking the clear pre-cum from it when he pulled back and away from me. "I have something for you before we get started." Picking up the package he had brought with him from the floor, he reached into it and pulled out a dong. I couldn't help gasping as he showed it to me, a wicked smile on his face. It was easily an inch wider than mine, and must have been about ten inches long. "I know you like big things inside you, so I brought you a gift! Now let's get some lube and I want to see you sit on this as you blow me."

Remembering the pain I had felt the first time I'd penetrated myself with my dong, I cringed and hoped that this stretching would hurt less. Alan was obviously excited at the anticipation of my discomfort, and I resigned myself to obeying him. He stood me up and bent me over the bed. Lubing up his fingers, he pressed them into me and quickly worked my ass until it was well moistened. Then he took the smaller dong from my dresser and lightly coating it, he worked it into me. He pulled it back and forth a number of times to assure himself that I was loosened, then told me to get back on my knees. He handed me the larger dong and the lube, "I am going to sit here and watch you. I want you to take the head of my cock in your mouth. You are not to let it out for any reason until the head of that dildo is inside of you. Once it is inside you, you are to let me out of your mouth and tell me. I will tell you what I want you to do after that."

I quickly coated the dong with lube from top to bottom leaving an extra drop on the tip. It was so large that I couldn't close my hand around the shaft, and the head seemed like it was almost the size of a tennis ball. I was scared of the damage this monster was about to do to me. I didn't even think I could actually get it in. But I was more scared of the people at work finding out about my secrets, so I determined to try.

I put it between my legs, lowered myself against it, and leaned forward to take Alan's cock in my mouth. I wrapped my lips just behind the head of his cock and closed my eyes. I began to lower myself on the dildo and felt the tip of it press up into me. As I pressed down harder the head of it flared and began to stretch my ass further and further. I breathed deeply through my nose and pushed down lower until I couldn't bear the pain any more. I lifted myself off of it, reached around behind me and smeared a little more lube on my anus. I lowered until the tip once again could go no further. I rubbed up and down against it in little increments trying to loosen my muscles. I was stretched so wide and I still had not gotten it in. I took one more deep breath through my nose, and dropped down forcefully, determined to get at least the tip into me. I felt it getting wider and wider as I pushed down, and suddenly with a sharp pain, I felt the head pass through my opening and into me. I quickly opened my mouth letting Alan's cock fall out and gasped. The size of the dildo inside me brought tears to my eyes. I clenched my teeth and fell forward against the side of the bed between Alan's legs, his cock resting against the side of my head above my ear and his balls against my face. "That was impressive" He said gently. "now turn around on your knees and put your head on your arms the way you did earlier today." I gingerly moved around so that I was facing away from him and leaned forward. As I did the remaining length of the dong rose into the air behind me, the head clenched tightly inside my ass.

As I began to take deep breaths and relax I felt a pressure against the dong. I glanced over my shoulder and saw that Alan had put his foot out and was pushing against the base of it, forcing it forward. It slid further into me and I could feel the extreme stretch of my ass around it. Inside me the head felt like a huge ball and as it got deeper and deeper it felt like it was going into my stomach. I tried not to cry, but the pain began to overwhelm me and the tears started rolling down the tip of my nose. I had not known that I was making noises suddenly became aware that I was moaning. I couldn't stay still and as he pushed I kept being pushed forward and down against the ground. My arms slid across the carpet and my elbows got carpet burn. Alan stopped pushing, and bending over me grabbed my hips and pulled me back until my calves and feet were under the bed and my ass was close to the edge. He sat back down on the side of the bed and using his foot went back to pushing at the base of the dong. He was obviously determined to get the whole thing inside of me. Realizing that it was getting dry, he pulled on it, pulling it out so that just the head was still inside me. The relief I felt was incredible, and incredibly enough the pain was quickly replaced with a oddly pleasurable feeling as my rectum clenched behind the head. My insides felt suddenly empty and burning with an inflammation that would only be soothed by being filled again.

As Alan squirted lube on the dong and spread it around I felt the coolness of it against my burning hole. He wiped his hands off on the back of my skirt, then sat back on the bed and put his foot up again. I felt the pressure of his foot on the dong, and began to press my ass back against him, feeling it enter me and begin to stretch my insides again. This time it got a little more than halfway in before it reached a place inside of me that seemed to block it. I was a little more relaxed this time, and was trying to push back against it in a little rhythm, rocking forward and back trying to take more of it in. I had just leaned forward and was beginning to press back when I felt a tremendous pressure. The huge dong inside me tore at my insides and slid deep into my stomach. I let out an involuntary scream, and collapsed on the floor. Alan had forced the whole thing into me, and as I fell forward his foot stayed on the back of it, pushing me down as he pushed it in, the balls at the base of it tight up against my ass cheeks. If I had been in pain before, I was in agony now! the whole length of the thing was inside me. I could feel the tip of it so far inside that it felt like it was in my stomach just under my heart. My body was shaking uncontrollably, and I could not move. I layed there, spread-eagled on the floor beside my bed, Alan standing above me with one foot on the base of the dong his weight on the back of it.

I was sobbing and tears were running down my face making a growing wet spot on the carpet. I don't know how long I lay there, but gradually my mind began to clear and I heard Alan above me. As I looked up between his legs I saw his balls swinging and his hips rocking forward and back as he jerked off. The shifting of his weight caused the enormous cock in my ass to rock in and out ever so slightly as well, and a warmth began to spread through me. The extreme sensitivity in my ass caused me to lay concentrating on it. I could feel each and every inch of it inside me. I could feel the shape of the head deep inside, feeling like it was in my stomach, tapered from the tip to the ridge of the corona. I could feel the width of it and the slight swelling of the shaft in the middle. The base of the shaft holding my anus open and the balls at the base snuggled up between my spread ass and legs, pressed against me, causing the nylon to rub the skin behind my balls as his foot rocked it in and out. The warmth turned to excitement, and gradually began to feel very good. My own cock hardened underneath me, and I started lifting my hips back against Alan's foot, and then as he pressed down I would stroke my cock against the floor. My nipples got hard and sensitive and my skin began to tingle up and down the back of my legs. The tingle began to spread up my ass, then my lower back, then further up my back to my shoulders until I was tingling all over.

Alan must have realized I was close to cumming, because he stepped back, leaned down and rolled me over. He straddled my leg so that his knee was against the dildo still forcing it tight against me and into my body and my other thigh was trapped between his legs. I reached down under the tights and began to stroke myself as well, but Alan grabbed my wrist and pulled my hand away. "Wait."

On his knees over me, he stroked himself faster and faster and just before he came he took the cup from the nightstand. Then he came into it, adding his cum to mine. My body was desperate for release as well and I wiggled my butt against his knee trying to get the dildo inside me to move enough to get me off. Alan just stayed still, watching me squirm for a moment. Then he leaned forward and down until his body was stretched above mine and I could feel heat from him as sweat dripped from his chest onto me. I watched his eyes carefully as he lowered his face to mine, then closed my eyes as he pressed his lips to mine. Everything went still and quiet as he kissed me, his tongue slipping between my lips to caress mine.

Breaking the kiss, Alan got back up to his knees, looked me in the eye and said, "you can't stop wiggling, can you? Do you want to come?" "Yes, oh yes! Please!" I pleaded with him. "you will have to do one more thing before I get you off." The tingling sensation on my skin had spread all over my body and I was desperate with need. "anything! Please, please, please…." He handed me the cup of cum and said, "First, do not touch yourself. If you do you will regret it. Second, I want you to swallow this. Not right away. When you start to cum, I want you to swallow this. I want you to get used to the idea that my cum in your mouth is your license to have your own orgasm." I moaned, "yesssss sir." "Now take a mouthful, but remember, don't swallow. And when you do cum drink that whole glass."

Alan sidled over between my legs. He grabbed them by the ankles and spread them over his shoulders. I tilted the cup between my lips and took half of its contents into my mouth. The thick spunk coated my tongue and tasted slightly salty. I swished it around and opened my mouth sticking my now-white tongue out at Alan. He smiled and nodded and reached down between my legs. He grabbed the base of the dildo and pulled. Even though it had been there for several minutes and my body had become accustomed to it, I was still not prepared for the pain this caused. I took a sharp breath through my nose and did everything in my power not to swallow the cum in my mouth. Alan began to work the dong in and out of me. Slowly the pain subsided and became an orgasmic heat as the friction built.

He was holding the base of it in both hands and rocking forward against me, forcing it in, then back, pulling it out until the only thing left inside was the head. He was moving more and more quickly and when I looked down between my legs I could almost imagine that he was really this large, and that he was fucking me with his own cock. As I closed my eyes and concentrated on the penetration filling my body and the cum coating my mouth, the tingling on my skin turned into a burn. The muscles in my abdomen started to spasm, then my legs started to quiver. My hands began to clench and my shoulders got very tight. Alan rocked faster against and into me and all of a sudden when the whole length of it in me, it was as if it had finally touched a button deep, deep inside of me. My whole body tensed, my back arched up off the floor and my ass clamped down on the huge cock, locking it in. Alan stopped and watched as my body went through convulsions. The intensity of the orgasm was so overwhelming that when I finally opened my eyes Alan was staring down at me with something resembling concern in his eyes. I smiled contentedly up at him the warmth radiating inside me, reached over to the glass of cum and putting it to my lips turned it up, pouring the entire contents into my mouth. I licked my lips, stuck my tongue out and licked as much of the inside of the rim of the glass as I could, then still smiling with complete content, looked Alan in the eye and swallowed.

I fell asleep after that, and was barely wakened when I felt Alan removing the dildo from my ass. He picked me up and put me on the bed, then kissed my cheek and left. I lay there tasting him on my tongue just before I drifted off to sleep again and into a fantasy dream. I dreamed of Alan. Of what he would do to me over the weekend, and what I would wear. I dreamed of my new life as Alan's girl.

    

    

    

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