This is a purely fictional tale about a man that decides to become a woman... warning .....
When I was eight years old, my mother walked in on me with her bra on, two crocket balls in the cups, feeling myself up and listening to the Radio. She didn’t get too angry, but we talked about it. At the time I remember feeling embarrassed, but very comfortable in her clothes. There was nothing said to my father, and we never mentioned it again.
In middle school I discovered my sisters underwear, and when she was out with friends, I would try on her clothes, and then carefully put them back the way I found them. Throughout high school I was the perfect guy, hooked up with women, dated, but always in the back of my mind I thought about the female body. In college, I lived alone, and while I still dated women, I bought my own clothes and at night, while masterbating to porn, always watching the woman’s body bounce on a big dick.
Let me interrupt and tell you more about me. I have always been the small guy. I ran cross country in high school. I’m 5’6” about 120, and thankfully, the only thing large about my body is my dick. Usually when I first hooked up with a girl, they made comments, and I actually had a few that wouldn’t go any further. Soft I’m 5 inches, hard, 9.5.
The moment happened one night when I was out with friends. I had smoked up earlier and was on the dance floor with a girl and while dancing behind her, she brought my hand up and put it on her chest. She was attractive, but I instantly got hard thinking about myself feeling my own chest. After dancing and drinks, I ditched my friends and went back to her place and we had sex. The entire time I fucked her I watched her tits and wanted them to be mine. When I came, I wasn’t me. I was her accepting myself.
When I went home I thought long and hard about it all. For days, the idea kept swimming in my mind. I began to wonder if I was gay. I went through my past, and thought about it all. I decided I would experiment in a non-threatening way. I went online and before I knew it, I was on my way to a house to meet a guy. I had arranged it so he would be sitting on the couch with his head covered. When I went in, I went straight to work. I knelt between his legs and unzipped his pants. His dick was soft, but when I put it in my mouth, it was like my entire life changed. I closed my eyes and immediately I was a woman. I grabbed my nonexistent tits. In my mind I was the woman that I had fucked. I had huge tits, and was enjoying a man. It wasn’t even the man that was such a turn on, it was me as a woman.
I wasn’t gay. I was straight. All the time I had been fucking women, I was turned on because I was the woman, not me. I went crazy on his dick, and before long he came. I wasn’t even present for most of the act, but as he came I could imagine it on my chest, in my pussy, the thoughts were too much for me to handle. When I left, I realized that I had cum in my pants. It was the most exciting night of my life.
At the time I was working as a web designer for a firm in California. I traveled some, but as they were outsourcing their web development, most of my time was spent at home, and there was little to no oversight. When I met my supervisor, his exact words were that he didn’t care if I smoked an ounce of pot a day, as long as I got the jobs done. When I made my next trip to LA, I visited a plastic surgen’s office and sat for a consultation. It was awkward at first. He came in and sat down on a chair opposite me. There was a lot of silence and eventually, he just looked at me and told me that his time was valuable, and he couldn’t waste much more time. The I spoke.
“I have been thinking for a long time that I am a woman. Since I was really little, I’ve wanted a woman’s body. That’s why I’m here.”
“Ok. So are you talking about total sexual reassignment surgery. How far do you want to go?”
“Everything except my penis.”
“Well you are looking at permanent hair removal, some speech lessons, hormone therapy, facial surgery, you have a good body structure, but maybe breast augmentation.”
“And you can do all that?”
“Well I can’t do all that right now. You need to make sure you really want this.”
“Well I’ve thought about this enough. I want to know how to get this started.”
“Well I’m not going to do anything until you prove that you really want to be a woman and have thought this through. I make it a policy that a patient should live as a woman for at least six months.”
I had my answer. “Ok start the clock. I want to schedule everything now.”
“Well Denise will give you a place to go to get the necessities and she can schedule the times for the next appointments.”
I left his office excited. I made the appointment six months from that day and drove to Wentworth Avenue to a store that they told me to visit. When I got there I handed them the letter from the Doctor, and the lady brought me to a back dressing room completely clueless about what was required.
When she came back in she had a check list. She asked me how large I wanted my breasts, and I was clueless. She brought in several breast forms and showed me the size. Still completely clueless, she said she would bring in some vests and I could try them on. We started small, and went through a few sizes. Everytime I wanted bigger. I wanted the tits the girl I fucked had. We moved up a vest and then suddenly, when I tried the next size on I felt they were me.
“Size 12 it is. You do want them big. Let me measure you to see what bra size you would be.”
She placed the measuring tape around me and then looked at me, “36F. Big. Let me go get you one.”
When she returned, I put the bra on and I began to feel more comfortable than I had ever been. We talked about other things I would need to do, she made some calls, I paid, and then went to the next address given me. There I was waxed from my neck down, except my pubic hair. When I got to my hotel room, I looked in the mirror, and was simply amazed at what I saw. I saw the beginnings of a body that I had always wanted.
When I went home I went shopping. I grew my hair out and loved every morning when I could get dressed. In six months I got a referral for hormone therapy, and after a few months, I really started seeing a big difference. I had gotten laser hair removal, my hair was thinning, and I even had the beginnings of breasts. I talked to the doctor several times on the phone, and by the time a year had rolled around, I made my final journey as a man. After much discussion with the doctor, I had insisted on 525cc on top of the muscle. He warned me that it would be a lot, a huge increase in size, and that it would be a more advanced surgery.
After everything was over, I laid in bed for weeks. I hurt all over and the bruising didn’t look like it would ever go away, but with time, everything faded. I was amazed with the transformation, and when it didn’t hurt anymore to touch my chest, I found myself jacking off in my bed feeling myself up. It wasn’t until a week later though that it all hit me. I looked in the mirror as I passed the window and for the first time, I saw my entire body. I would never have recognized myself. I looked like a woman, outside my dick, but if I tucked it between my legs, you couldn’t tell. I had curves, not huge curves, but my tits went a long way. They were crazy tight, but the doctor said the skin would stretch. My face had smoothed out with the surgeries. I had no facial hair, and with makeup and my hair no long, you would have a hard time noticing. Along with the fact that my voice had always been a bit higher than most guys, unless you found my dick there was no telling I was born a man. It made me the happiest I had ever been.
The only problem was that I had never spent as much money as I did at this point. I bought bras and panties, dresses and skirts. I simply loved to get one of the girls in the stores to help me, because they never even hinted that I was anything more than a woman, but I was still scared to make the next step. There were other problems. My back did hurt at first. Also, no matter what I did, running hurt. I didn’t want to go swimming because I knew there was one thing I couldn’t hide. Weeks past. I was the happiest I had ever been.
It was a Friday, and I had been inside my apartment for two weeks without leaving other than going to the grocery store. I decided I would go out for a beer and a meal. I put on a cut jean skirt and a black blouse, wearing panties and no bra since the firmness of my breast, although easing, still allowed me to go without a bra, even at my large size. I was sat at the bar, and ordered a salad and a beer, and after eating I order a beer and watched the baseball game on the television above the bar. After some time, I came to the end of my beer, and I thought about going home, but suddenly something stopped me. A guy had sat beside me and began looking over at me.
“Let me buy you another beer.”
I was shocked. It was clear he was hitting on me. I accepted the beer, and we talked about what he was doing in town, that he was leaving the next day, and that he was bored in his hotel room and decided to come out and “mingle with the people.” We laughed several times, and there was slight touching, and more beers. Eventually he told me he was heading back to his room, and there was a pause. I didn’t know what to say, but thankfully, he interrupted the silence.
“So hey, this is very forward, but would you like to come back to my room and have a drink?”
I was scared stiff. I tried not to think what would happen, but eventually, and I don’t know where it came from, but I said yes. I stood up from the stool and realized just how drunk I was. He clearly noticed too, because he put his arm around me and steadied me. We walked next door to his hotel, and he guided me into the elevator. He leaned against the back wall and I stood in front of him looking at the numbers begin to change. He grabbed my waist when it read floor 2, and had pulled me back against him by floor 4. He was kissing my neck by floor six, and when the doors opened to floor 7, it was all I could do to mask my hard on. He passed me and grabbed my hand to pull me to his room, and with my other hand, I pulled my dick under the waist band to mask it. I didn’t know how I would deal with the issue when I came up, and from the activity on the elevator, I knew it would be coming up.
When we got in the room, he turned to me and kissed me. I tried to stand away from him, but it was difficult. The feeling I felt was amazing. I felt so feminine. I felt desired, sexy. It felt as if all my life had been leading to that moment in time. I broke the kiss and immediately told him I needed to use the bathroom.
I peed, but it took a while to get my dick to go down. When I finally exited the bathroom, he was sitting on the bed drinking a mixed drink. I sat on the chair at the desk, and he asked if he could make me a drink. I said yes, and then we sat in silence as I sipped the very strong burbon and coke.
I finished my drink with little to no conversation, I began to think that nothing was going to happened, when he suddenly stood up from the bed, came over to me and bent down and kissed me. It was passionate, heavy. He forced me back in the chair with his kiss, and before I knew it his hand was on my chest. I had felt my chest a hundred times, but his touch was something completely different. He squeezed and tugged, found my nipples, now so hard they almost hurt, and rubbed them. He pulled back and then tried to go under my blouse, but I stopped him and pulled back to unbutton it. When it was off, he dove on my nipples. He went back and forth between them. The feeling was amazing. I lost myself in his touch and his mouth. Then I felt his hand on my thigh, and I came back to reality. I pushed him off of me and for a second, he seemed confused. I stood up to face him and then pushed him back on the bed. It was all I knew to do. Once seated, I unzipped his pants and tried to pull them off him. I failed. I got to my knees and tried to use leverage, but it didn’t work. Only then did he stand again, his crotch now directly in my face, and he pulled them down. With them came his boxers, and now naked, his cock sat inches from my face. I reached up and grabbed my own tit and in the same motion, took his dick in my mouth.
I had sucked a dick before, but when I did, I did it blind. My mind was elsewhere. Now, with his head in my mouth, the feeling was electric. Heat moved through my body. Every sensation was apparent. The soft skin of the bridge of his head on my lips, the softness of his hard dick against my lips and tongue, the slow movement of the underside of his dick against my tongue, and the fullness of his cock in my mouth all filled me with a lust I had never experienced before. I released my tit and put both my hands against his thighs and rubbed up and down their whiteness. I felt the tightness of his muscles as I moved down his cock. I sucked him slow, with caution as the memories of women chocking on my dick began to make sense as the size of him filled my mouth completely. I started with a few inches, each time moving further on his dick until I felt the head of his dick hit the back of my throat. I made sure I squeezed his shaft with my lips as I moved up and down on him, and once I knew he was fully hard, I released him from my mouth, and pushed against him lightly so he would sit down on the edge of the bed. I moved closer to him, and when the head of his dick moved back into my mouth, his hands started rubbing my head and shoulders.
He wasn’t extremely large, but his dick was smooth and he did not have any hair. The smell was intoxicating. I cupped his balls with my hands, took breaks from sucking and licked up and down his shaft. When I was out of breath from sucking him, I put his balls in my mouth, a feeling that nearly sent me over the edge. When he moved his hands off my head and tried to reach around and grab my left tit, I nearly came in my pants. He leaned over to try and get a better grip on both my tits as I sucked, and to assist him, I moved off my knees and sat up so he could hold them both without struggling. He pushed them together, grabbed them and pulled them apart, found my nipples and swirled around my aereolas. When he pinched my nipples I released his dick from my mouth and moaned.
I didn’t want to stop sucking him. It was heaven to have him in my mouth, but I felt him trying to lift me. I released him as I thought he wanted me to, and when I did, he asked me to take my skirt off. I panicked.
“Not yet. I want to suck you off. Lay back on the bed.”
The command didn’t seem to bother him. He laid back on the bed, his legs still hanging over the side, and he put his hands over his head. When he did, standing over him, gazing down on his cock, I saw him perfectly framed by my breasts. It was the inspiration I needed. I placed my tits on either side of his cock and pushed my tits together. He fell out a few times, but eventually, I found the right hold to keep him between them. I started moving them up and down on his dick, his head barely peaking out when I was all the way down on him, and I thought to myself that this was the first time I, as a woman, was doing something I could not have done as a man. My saliva provided all the lubrication we needed. The feeling was exhilarating, but the more I moved my tits on him, the more I wanted him back in my mouth. I looked up at him and saw his hands starting to grab the comforter, and that was the cue I needed. I released my tits and his dick slapped against his stomach, and when I found the floor with my knees, I placed his dick back in my mouth. I didn’t go slow anymore. I found the depth I could take, and started moving with force on his cock. He moaned and moved on the bed, and I could feel him tense. His balls retracted, and I knew it was coming. I started just sucking the head, taking only an inch or two more beyond it in my mouth with furious speed. I moved my tongue on his head and the underside of his dick, and with my tongue flicking his hole, he finally exploded. The surge surprised me, but I fought the reflex to withdraw. When the first shot came, I felt the force of the shot against my tongue and immediately the taste filled my mouth. The second shot was thicker, and with much more force, and it splattered against he back of my throat. As he kept cumming, the only sensation I felt was the increasing volume in my mouth, the change in taste and feel in my mouth from a thinner and salty taste to a thicker more bitter taste. I could tell he was cumming less and less, eventually to the point where I knew he was done, but with his cum still filling my mouth, I didn’t want to release him. He bucked on the bed with my every movement, and he sat up on his elbows and clearly was not wanting, but urging me to stop. As his stiffness relaxed, I finally let him slide out of my mouth, but as I did, some of his cum leaked out of my mouth before I could close my lips all the way. It slid out of the corner of my mouth and down my chin. I stood and then sat on the edge of the bed, his cum still in my mouth, me swirling it around so I could concentrate on the feel. With his dick gone, it appeared to be much less than it felt like as I was sucking him, and with my eyes closed concentrating on his cum in my mouth, I felt his hand rub against my back.
“Do you need to go to the bathroom?”
I turned to look at him and realized that he much think that I wasn’t to spit him out. I smiled and swallowed him at the same time, feeling his load slide down the back of my throat, coating the back of my tongue with the thin glaze that cum provides to remind you just how it tastes and feels.
“No I’m good. I just wanted to take it all in.”
I fell back on the bed, my tits swaying back and forth as the full weight of my body came to a stop against the mattress. He laid next to me on his side, his left hand rubbing my tits as I closed my eyes, missing his gaze and concentrating on the feel of his hand against my chest. Eventually I turned to face him and opened my eyes, and when I did, his mouth found mine and we kissed deeply for some time. Our tongues swirled together, and we finally broke from each other.
“I love the taste of my cum in your mouth.”
“Really?” I was propped on my side, my right tit resting on my left. Every once and a while he would reach up and pet one. I brought my right leg over to rest my knee on the bed to cover my raging hardon.
“Yeah I think its so sexy.”
“I didn’t know men liked that.”
“Well I don’t know about other men, just know what I like, and your just fucking super sexy.”
I knew I was passable, knew when I looked in the mirror naked that most guys would miss the small cues that I might be what I am, but then again, there are women that had worse bodies than I do. Big tits go a long way to mask anything, but even knowing all this, there was still doubt in my mind, so when he said what he said, I finally felt that I was a woman both in my eyes and the eyes of others.
“Thank you do much. I was clearly blushing.”
“No problem. So when do I get to take care of you?”
“Oh….” I paused and I know he saw me panic. “Um, that’s not necessary.”
“What you don’t want to cum?”
“No its not that.”
He started rubbing my chest and moving his hand down my stomach. I retracted and stood up from the bed. I didn’t know what to say.
“Did I do something wrong?”
“No its not you.”
“Then what? I have no problems doing whatever you want.”
“I don’t know what to say. I’m… I’m… Well I’m just not what you think.”
He smiled at me.
“What are you smiling at?” I was so confused. It wasn’t going the way I thought.
“Nothing. You. Your so sweet to worry about me.”
“I just think you’ll be disappointed.”
“Why would you say that?”
“I just know.”
“Why would I be disappointed? From the feel of it, you seem to have one hell of a cock.”
I was shocked. He knew. I didn’t know what to say. “You knew?”
“Well it was kinda hard to miss when we kissed. You were poking into my thigh.”
“I’m so embarrassed.” I covered my face. “You mean you knew and you still wanted to mess around?”
“Hell it made me want you more.” He sat up on the edge of the bed and kissed my nipples. He placed his hands on my thighs, and I knew that I didn’t have to say anything else. In the past, I was never this reluctant to get a blow job, but now I was.
He moved his hands to my inner thighs, and moved my skirt up. When he got it up so he could see my bulge, I reached down, unbuttoned it and allowed it to drop to the floor. I stood before him with my black panties and my soft cock held away from his face by a thin sheet of satin. I could tell he was nervous, but it didn’t stop him. He pulled my panties down to my ankles and when he came back my dick was right in front of his face. Without any encouragement he took my soft dick in his mouth. He began sucking, and it was clear that he had never done it before. He grazed my dick with his teeth, he didn’t grip it with his lips, but I could tell he was trying, and from my vantage point, my tits in the foreground, him sucking my dick beyond, it was more than enough even to enjoy a horrible blow job. When I was fully hard, he pulled me out of his mouth and just looked up and down my dick. When he put me back in his mouth, he slowly got better. When he moved his hands from my ass to my tits, I instantly went from reluctant to fully turned on, and when he started squeezing, it was all I could do to not explode. After about ten minutes, I couldn’t take it anymore.
“I’m going to cum.” He didn’t stop or slow down. I had learned through the years that I should warn the women that had sucked me because I cum a lot.
I released when he gave my tits a squeeze, and when I did, I thought I would blow the back of his head off. I came with such force that it even surprised me, and as I squirted a third and forth time, I felt him gag a bit, but to his credit, he kept on. Looking down on him, cum was dripping out both sides of his mouth.
When I pulled out, he laid back on the bed and started telling me how amazing that was. He went on and on about how it was anything but nasty, how it was the most sexy thing that he had ever done. I laid down beside him, my wet cock resting against his leg and my right tit resting against his chest. I started rubbing his chest, and playing with his nipples, and eventually I laid on my back and although he was rubbing my thigh, I slipped off to sleep.
I woke up hours later under the covers, still naked, with him resting his head on my shoulder and his arm stretched over my stomach. I laid there for a while, just looking at him and looking at my body. I had always wanted to know what a woman felt like being with a man. It wasn’t just the sex. I wanted to know what it was like to be the center of attention, have a man desire my body, feel his hands on my body.
I took his hand from my stomach and put it on my chest. I made sure not to wake him, and he didn’t grab me, but just feeling his hand on my tit and covering my nipple, I was in heaven. I felt the coarse skin from his hand resting against the taunt skin of my new breasts, his arm under my left boob. The whole experience was amazing. I closed my eyes and wondered what it would be like to be married, be a wife, have children, and it must not have been long before I fell asleep, because there weren’t many other thoughts.
When I woke, I was on my side facing the wall, and when I turned over he was gone. After a few seconds, I woke up and heard the shower going. I sat up over the side of the bed, and walked into the bathroom.
“I thought you left.” I sat down on the toilet and peed.
He poked his head out, covered in shampoo, and looked me up and down. “You look sexy as hell. Want to join me?”
I stood up and without saying anything I pulled back the shower curtain and stepped in. The water was hot, and before I could even move, he was on me. He kissed me deep, and with both arms around me, he squeezed me tight. I closed my eyes and took it all in. He pulled away, and took the soap and started cleaning my body. I turned around for him to clean my back, and after some times rubbing the soap up my back and over my ass, he reached around and lathered up my chest. The whole exchange took only a few minutes, but in that time, my dick was standing to attention to match his hard cock pressing against my back. I turned to face him, and took the soap from his hand and began cleaning his cock with the soap. At that moment, I wanted him to fuck me so bad, but my fear was still overwhelming. I made him swap places with me, and in seconds I was on my knees in the shower, the water rushing over my head, his cock in the back of my throat. I sucked him with reckless abandon, forcing him against he back wall and myself out of the water. I cupped his balls and player with his ass, and when I managed to push a finger into his ass, he exploded in my mouth. I didn’t savour his cum this time. I swallowed as he shot, and before long he grew soft in my mouth.
When I stood, it seemed like he didn’t know what to do. I kissed him, and told him to turn off the water, saving him from the awkward decision of knowing whether he should return the favor. I stepped out and grabbed a towel and dried myself, making sure to face him and push my tits well beyond the required time to get them dry. We made small talk, not sexual, got dressed, and it seemed we had reached the point where it was time to say goodbyes.
“I’ll be in town for four more days, and I would really like to see you tonight.”
“Really?” I was shocked. Even though it had gone so well, I figured that he would want to kinda end it.
“Hell yeah. Why wouldn’t I?”
“I don’t know. Forget it. I would love to.”
“Ok. How bout dinner and then take it from there.”
“Sounds great. Do you want me to meet you here?”
“Sure. Here is a key. I gotta work most of the day, but I’ll be back here about six.”
We kissed like I was his house wife sending him off to work, and as he made his way to his car, I took the walk of shame and found my car sitting alone in the parking lot.
I went home and checked my email, answered a few questions that were posed by some clients, and with luck, there was not much work to be done. I had a big project I was working on, but because I had pretty much been a shut in over the last few weeks, I was ahead of schedule.
I put on fresh underwear, bra, slid on a clean skirt (I loved wearing skirts), two tank tops, and slipped on my Ugg boots. I decided to spend the day doing some much needed shopping. I made my way to the mall and stopped in the strip mall across the street at the store where I had bought all my bras. Since my augmentation surgery, I had followed the regiment of massage and medication, and my breasts had loosened considerably. After a month post-op, my breasts were still so tight that I didn’t really need a bra, but now, I could tell a big difference and since my size was not to be found in Victoria Secret, I paid for the good bras that actually helped support the new weight to my body.
I hugged Shelly when I went in, and she grabbed my chest and asked me how it was having my big boobs. We laughed for a minute, and I gossiped a bit about my big night. I told her I wanted a few sexy bras and maybe a good outfit for tonight.
“Well tell me, how did he like the girls?”
“I think he loved them. He kept coming back.” We laughed again. She reached and grabbed them again and smiled.
“They look and feel really good. Better than they did when I first saw you.”
Shelly had told me that I needed to become a lesbian every time I came in, and this time was no different. I let her have her fun, and then without warning she turned around and made her way through the store picking things out for me to try on. She came back and grabbed my hand and pulled me into a dressing room. We tried on the bras first, all cute, but preferred the lace to the full coverage cup. I picked out two. Then she pulled a raunchy black number that had garders and a G-String. I didn’t think anything about changing in front of her. She sat on the bench and I took off my clothes and once naked, I took the outfit from her and started unhooking the back.
“Damn girl. Your dick is huge.”
“Thanks. I like everything big.”
“No shit. You really are the best of both worlds. I don’t even like dick, but that thing is pretty damn impressive.”
I smiled at her and put it on, adjusted my boobs in the cups and then looked in the mirror. From the waist up, it looked amazing. I felt so sexy, but from the waist down, it was pretty hard to miss that I had a dick. It didn’t hide anything. I turned to look at her.
“Wow. Can’t cover that thing up can ya?”
“Not in this. What else you got?”
“You don’t like it?”
“Sure I do, but I think I would like something that makes me forget I have a dick.”
She handed me a red teddy with loose satin bottoms, and once on, I new I had found it. It showed plenty of cleavage without being overly slutty and although my dick somewhat hung out the side of the bottoms, with a little adjustment, I could hide it.
I paid for everything and kissed Shelly which was followed by the familiar tit grab and smile.
“You know where I am if you want me to give you a full review on those big things you got.”
I smiled at her and got in the car. I went to the mall and made the rounds to the various stores I liked. I bought a really cute dress, a few tops, some panties, and a free flowing skirt. Tired and hungry, I got some food and got back into my car to head home. On the way, I noticed the adult book store that I had passed about a million times without ever stopping. I decided today was the day. I pulled in and walked in. It was the middle of the day, but there were still more people in there than I had thought there would be. I didn’t have an agenda, had no clue what I wanted to look at, so I simply walked around the store and took inventory. In the middle of the store were racks and racks of videos. I looked at the videos, noticed the categories and was simply amazed at the shear volume of titles and variety of topics. Whole sections were designated to fisting, gangbangs, gay, big tits, anal, and the topics went on and on. When I stopped for more than a minute, I noticed that men would get closer to me, clearly not looking at the titles. I shifted everytime it happened, but eventually, concentrating so much on staying away from the men in the store, I found myself in front of the gang bang section. I picked up a video and looked at the title. “Mommy Gangbang.” Wow. I didn’t notice that I was now standing directly beside a guy. He grabbed a video right in front of me. He smiled, made no attempt to look at the video case, and put his face right next to my ear.
“I’m going to preview this movie. Why don’t you check yours out too.” He looked at the title in my hand. “Interesting interests.” He smiled again, and as he passed by me from behind, he drug his hand across my ass.
I blindly followed him and waited as the guy sitting in a chair opened the video and walked him into a booth. When he came back, he smiled, took the video and did the same. I walked in behind him and as he moved to go out, he grabbed my tit and smiled again. I sat down in the chair as the video started up, and the affect was startling. There was not much back story. I wasn’t sure if the video was started in mid movie or not, but after a few moments, it was clear that the woman in the video was getting ready to have quite a few men take care of business. Suddenly there was a knock on the wall to my right. On the wall there was a sliding door, and because of the knock I slid the door open and then heard the door on the other side slide open. The wall wasn’t very thick, and the opening revealed a hole about six inches in diameter.
Before I knew what was happening, a dick came shooting through the opening. It was large, but not huge, and I was so shocked that I didn’t know what to do. Instinct took over. I grabbed it and started to move my hand up and down. It was smooth and there was just a hint of pubic hair coming through. I looked up and saw there was a bar on the wall toward the ceiling, and I could tell that the man on the other side of the wall was probably holding on for leverage. I didn’t wait any longer. I slid my chair close to the opening and put the head of his dick in my mouth. God I loved sucking dick. Even though I had sucked last night and this morning, the feeling was still overwhelming and like I had never experienced it before. I sucked without much variety and before long he started to cum. I wasn’t ready for it. It wasn’t like the night before. He came in large streams with a lot of force. The taste and the feel of his cum made me instantly hard. I swallowed and sucked, and eventually he pulled back and closed the window.
As his door closed, there was another knock behind me. I didn’t take a breath. I adjusted the chair and by the time I slid the door open and his dick was coming through the hole, I had him in my mouth. He was unimpressive in size and didn’t last long, but the entire experience was overwhelming. I adjusted my dick and looked at the screen as I started to leave. The woman in the movie had a dick in her pussy and ass, one in her mouth, and was jacking off two guys with her hands. How she held her balance was beyond me.
When I left the booth, I saw the guy I had just sucked. He smiled at me, but didn’t keep eye contact. I walked through the isles of videos and it was as if the entire store knew what I had just sucked two guys off. I went to the wall with the dildos, looked a few packages, and then found the butt plugs. I picked two, one small, one large, and then found a mountable dildo that ejaculated when you squeezed a small pump in the balls. I also bought a large thing of Astroglide. I paid and almost ran to my car. When I got there I sat in silence for a while, and then trying to figure out what to do next, I settled on heading to the hotel and set up house before he got home.
I brought my purchases up to the room, and ordered room service. While I was waiting, I took out what I bought and tried on everything so I could see it in the mirror. I really liked the bras I bought and modeled them in the mirror. I put on one of the skirts, and just when I was getting ready to complete the look there was a knock on the door. I didn’t think. With all the events of the last 24 hours, I just went to the door and opened it. The guy with the tray had to be barely out of high school. He was over six foot tall, black, very attractive, and standing in front of him was me, in a bra and a skirt. I saw his eyes move up and down my body.
“You ordered something to eat?”
“Yes, you can put it on the table.”
He walked past me, his eyes never leaving my chest. When he got to the table he sat the food down and looked at the bed. On it I had all my clothes, and the sex toys I had purchased. Right beside the tray was the lube I had bought. He turned to me and smiled.
“Will that be all?”
“Yes. Thank you.” He went to leave, I could tell with some disappointment, but I stopped him. “Wait. I should give you something.”
I reached in my purse and took out a five dollar bill and handed it to him. He looked at it and then me, smiled, took a pen out of his pocket and wrote something on a piece of paper from his pocket. He handed me the paper, “Call me if you need anything else. I work days, so anything you might want I can help you out with it.”
I thanked him, and knew that I could have ended naked with him, but I was too chicken and way too hungry. He left, and I sat down and ate. When I was done, I looked at the clock and it was only 2, so I took off my clothes, turned down the AC and crawled under the covers. When I woke it was 3:50. I turned on the TV, went to the bathroom, and when I came out I saw the toys I bought. I took them out of their packaging and looked at them in detail. I started with the big one, and once I had it out, I realized that it was a better idea than it was a practical instrument for my pleasure. It was enormous, and I thought way too big for my ass. I took out the smaller one and looked at it. It was about 6 inches long with a triangle shape that led to a ridge and then a straight shaft to the base. At first I was reluctant, but then I just dove for the lube.
I struggled for a place to do it. Eventually, I settled on the table. After the book store and the entire days events, my dick was rock hard just with the expectation of what was to come. I spit on the table, and then placed the plug on the spit, pushing it down so the suction cup was in place. I squirted a ton of lube on my hand and rubbed it on the plug and then on my ass. I stood over the corner of the table, and lowered myself on top of it. When it got the edge of my ass, I paused. Not even inside me yet, it felt too large to take. I pushed down on it a bit and felt myself parting. I pulled back and then lowered. Each time I did it, it went further in. My ass completely resisted, but after some time, all of a sudden, it slid all the way in and past the lip of the plug. The feeling was quick and amazing. It wasn’t painful, but definitely different and strange. When I pushed down, the feeling was intense and amazing. My cock reacted immeditately. I wasn’t hard, but the pressure inside me was amazing and I felt like I would cum. I heard a beep and then a click and then the door suddenly began opening.
He walked in looking at the ground, briefcase in hand. When I heard the door open, I stood, the plug still in my ass, and although he walked in with his eyes on the ground, when he heard someone in the room, he quickly looked up at me. I was instantly embarrassed, but I tried my best to act like everything was ok.
“I was waiting for you. Long day at work?”
He smiled at me. “Yes it was, but it was worth if I get to come back to you.”
“Your sweet.” I did my best to walk toward him, and hugged him. He put his arms around me and then kissed me.
“I see you went shopping.”
“Yeah. I thought you would enjoy.”
“Well I enjoy what I’m seeing now.” He reached down and grabbed my dick. “I never thought I would be so turned on by this.”
“Well I always knew I would like that.” I smile at him.
“Hey, I’m going to shower, then maybe we can get some food?”
“Sure. Go ahead. I’ll make you a drink.”
When he got in the shower, I turned and took the plug out of my ass. I had almost gotten use to it, and it felt like my ass was still open. I wiped it off on my dirty panties, and put it and the other toys in the bag they came in and put them in the closet. I scurried around the room cleaning up, putting the lube away in the beside table, and then made him a bourbon and coke. When I made my way in the bathroom, he was stepping out.
“Oh I was going to join you.”
“Want me to get back in.” He was smiling at me.
“No. Here drink this. I’ll dry you off.”
He took the drink from me and started drinking. I grabbed the towel from his hand and started at his chest. I worked slowly, intentionally making it a seduction. I avoided his cock on purpose, turning him around and drying his back, down his legs, and then once I was on my knees, I turned him around and dried his cock. He was semi hard at this point, and once I had taken a rub or two with the towel, I couldn’t stand it anymore. I dropped the towel on the floor, and put his cock in my mouth. It tasted wonderful. I sucked for a few minutes. His hands rubbed my head, and now hard, I let it tickle the back of my throat. When he started grabbing the back of my head harder, I stopped. I let his dick slide from my mouth, and looked up at him.
“Is everything ok?”
“Yeah. Lets go the bed.”
I stood and grabbed his hand and then forced him to lay back on the bed. I put his dick in my mouth for a few sucks, and pushed it against his stomach and licked his balls. I swirled my tongue around them, took them in my mouth, and then with my thumb lifted them, and found his ass. I stuck my tongue into his ass and he thrashed backwards. I swirled it around his opening and with every movement his entire body moved.
“God that feels amazing.”
I stopped. I stood up and crawled on the bed beside him. My knees were just on the be, and I leaned over and kissed him. With his left hand he grabbed my face and pulled me closer so we kissed deeper. With his right he reached under me and took my left tit in his hand.
“I want you to fuck me.”
“Are you sure?”
“Yes I want to feel your cock inside me.”
He didn’t hesitate. He stood and got behind me.
“Wait.” I laid down on the bed and reached the bedside table. I got the lube and then sat in front of him. I squeezed out a glob and lotioned up his dick. Then I got back on my knees in front of him and reached between my legs, applied a huge glob on my ass hole. I felt him move towards me and put the head of his dick against my ass.
“Go slow.” I braced my self against the bed and put my head on the mattress.
He pushed the head of his dick harder against my ass, and it began to part with the pressure. The head of his dick entered me without much effort, no doubt because of the plug, but as more and more of him entered me, the pressure increased and the discomfort grew. I got worried. I wanted to get fucked really bad, but this was not what I was looking for. When I worried more, I squeezed on him, and the squeezing hurt. He stopped moving, not all the way in, and started rubbing my back. The feeling was very relaxing, and before I knew it, with a slight push, he got all the way inside me. I was breathing deep, he was stopped, rubbing my back and ass. I tried to concentrate on him in my ass, and although I wanted to squeeze down, I started to feel normal, and then all of a sudden, strangely enough, my ass seemed to completely relax. He obviously felt it too, because about the same time, he started to pull out and push back in slightly.
My breath sped up, and my ass burnt, but quickly, the discomfort and burning began to feel amazing. He began to push in deeper and harder. His body began to slap against my ass, and his dick began to come almost all the way out of me before it moved all the way in. The pace quickened and any discomfort went away. The feeling of his dick inside me was simply amazing, and the movement made me aware of how much I was parting and allowing him to move inside me. When he got all the way in, the pressure against my prostate was overwhelming, and each time it felt like I was on the breach of cumming. When he started grabbing my hips and the slapping against my ass grew, I knew he was close. I felt his balls slap against mine, and I felt my own orgasm growing. That’s when it happened. I felt a huge surge of heat in my ass, and then all friction was gone. I felt him move in my ass, but it was without the pulling against my insides. He slammed harder and I heard him grunting, and with every push inside me the wetness grew. The sound of him hitting my ass was replaced by a splashing sound. I felt his cum leaking out of my ass as he continued to fuck me and drip down my balls. When he was finally done, he pushed all the way inside of me, and collapsed on top of me, forcing me onto my stomach, panting. When he started to grow soft, he rolled off me and onto his back, and as he did, I turned over and laid next to him, resting my head on his chest as he began to relax.
“That was amazing. How did it feel to take a girl’s cherry?”
“That was your first time?”
“Yup. First time to feel a guy explode inside me.”
“You could feel it when I came?”
“Oh god yes. It was amazing.”
“Well did you cum?”
“No but its ok.”
“Are you sure?”
“Yeah. Later tonight.”
We went out and ate, come back to the room, and messed around. I sucked him off, and he drank a lot, and before long, he was drunk. He continued to drink as we sat in sat in bed and watched tv, and before long, when I tried to talk to him, he was merely grunts and half sentences. I hadn’t cum all night long.
He was laying on his side, and my dick was rock hard. I pushed on his shoulder and there was only a slight sound. I reached around and grabbed his dick and started to pull on it and even after a few minutes, there was no movement from him and no sound. I reached to his ass and started playing, but there was no movement. I pushed a finger in him and he didn’t flinch. He was drunker than I thought. I rolled over and thought the better of it, and then the horniness of it all was too much. I reached over and grabbed the lube and soaked my dick. Then I put a large amount, probably way too much on his ass hole and put the head against his ass. Still no movement. When I pushed in a bit more, he moved slightly, but didn’t resist. He didn’t seem to be tensing up at all. When I managed to get all the way inside him, I knew he had to be beyond passed out. I began pushing in and out of him, the dead ass hole neither resisting or participating. I fucked him slow until I was ready to cum, and then I pushed all the way inside him and ejaculated. When I shot he stirred, but didn’t resist and didn’t wake. When I was done cumming, I pushed all the way inside him and rested there until I softened and fell out of him. I watched as the cum slowly leaked out of his ass, and there was a huge wave of remorse that washed over me as I realized that I had semi raped him.
I got out of bed and collected my things. I put everything in the dirty clothes bag, dressed in whatever I could find, and without saying goodbye, I made my way to my car. Once there I closed my eyes, and thought long and hard about the days. Once home, I took a shower, collapsed in bed, and didn’t wake up till the next evening.