My Virgin Ass

By Pudmeister

Original link: https://www.lushstories.com/stories/trans/my-virgin-ass.aspx

Tags: crossdressing, first time, anal, oral.

Added: 16 Nov 2012 Views: 22499 Avg Score: 4.91

A straight married guy picks up a virgin tranny.
I sat in my car in the club parking lot, not able to move. I was dressed to the nines and my plan had been to enter this club and find a date for the night. A male date. It was a club that encouraged Transsexuals and Cross dressers as patrons to hook up with straight or bisexual males. I am not sure if I am a Tran sexual but I sure was crossdressing tonight. Why was I hesitating? This is what I desired right?

Earlier I had spent time getting ready over at my friend Courtney's house. She was a hairdresser and also did makeup. She knew what she was doing when it came to making a guy look like a woman. I had been on female hormones for 4 yrs. They had caused my breasts to grow to a 38C size. I had pretty much stopped growing body hair and my balls and penis had shrunk so much they didn't really function. I took a shower at Courtney's. I was in pretty good shape but certainly not a model. I stepped out of the shower and Courtney checked me over for any stray hair. She lifted my breasts up and said she had an idea for what I should wear tonight. I put a robe on and sat down for her to do my makeup.

She knew how to hide the flaws in my face and to highlight things that would make me look more feminine without looking trashy. I had been trying to grow my hair out but it wasn't quite there yet. Courtney put a wig on me that matched my natural hair color. After my makeup, nails and hair was done we walked into her bedroom to see what she had picked out. I slipped a gaff on to hide my tiny cock and balls. Once on you could not tell I had them. I put on sheer black hose and a garter to keep them up. I was going to wear a bra but she said no. Instead I should wear a corset. The one she had laced in the back and zipped up the front. With some pulling and tugging we got it on me. It came up to just under my breasts pushing them up and out. It made them look much bigger. It made my waist look much smaller too. I put a black mini skirt on and a black leather jacket over the corset. It zipped up but not over my boobs. I was definitely showing plenty of cleavage. I put my fav pair of heels on and all Courtney could say was WOW. I looked and turned in the mirror and thought yes wow. I looked like a hot Milf on the prowl.

So here I sat outside the club. I had come prepared to meet a guy and go home with him. He would know I was a genetic male but it wouldn't matter. He would want to have sex with me and I would let him. It would be my first time to have anal sex with a man. It was something I had wanted to do for a long time and I had made the decision to go through with it. I had prepared myself at Courtney's. I was all cleaned out and lubed up inside. I looked at myself in the rear view mirror. I saw a good looking lady looking back. I checked my makeup and took a deep breath and opened the car door.

My heels clicked on the sidewalk as I approached the door to the club. The doorman smiled at me as I walked up and then opened the door for me to enter. It was dark inside and it took a moment for my eyes to adjust. It was a typical club layout. A long bar with a dance floor surrounded by tables and chairs. It wasn't crowded, maybe about half full. I scanned the room and saw men of all ages. Some were sitting alone and some were talking to women. Or should I say guys dressed up as women. Some looked great and others needed work. I decided to head to the bar and order a drink.

I was able to negotiate the bar stool and sit down in my mini skirt while crossing my legs. I had worked on feminine movements with Courtney and it helped. I caught the bartenders eye and ordered a drink. As he set it in front of me I took out my purse to pay and he said it was taken care of. I looked at it ans smiled thinking the night might just be getting ready to be interesting. I sipped my drink and in a couple of minutes I saw someone approach out of the corner of my eye. I turned to look and saw a decent looking young man walk up and sit down next to me. I smiled at him and said Hi. I had been practicing using a female voice. Courtney said I had a breathy smoky voice. Very sexy she said.

He introduced himself as Jimmy. I estimated him to be late 20's early 30's. I smiled and said my name was Anita. He chuckled and said as in I needs date? I said what? He chuckled and said sorry bad joke. I thought a minute then got it and laughed out loud placing my hand on his chest as I did. I left it there for a moment. I noticed he had a wedding ring on. So this guy was married and out prowling around. I doubted he was bi. Maybe just a curious straight guy. We made some small talk getting more comfortable with each other. He admitted to being married. She was out of town with their two kids. After their second was born she basically gave up sex. He said she was a domineering bitch. He could do nothing right and she yelled all the time. He had decided to explore a desire he had for a long time. That's why he was here tonight. We had a couple more drinks and he got the courage to ask me if I wanted to leave the club with him and go to his place. I decided that I like this guy and I decided to take a chance. We left the club together and I followed him to his house.

He told me to park across the street from his house. As I walked up to the door he opened it. It was a typical house in a typical suburb. He asked me if I wanted a drink and I said yes. I downed the drink and walked over to him. I put my hand on his chest again and smiled at him. He smiled back and I knelt down in front of him. This is something I had never done before but I wanted to try. I reached out and unzipped his pants. I undid his belt and unbuttoned his pants. Pulling them down along with his underwear revealed a very nice size cock that was getting harder by the second. It was poking straight out, about an inch from my face. I leaned forward enough to kiss the tip of his cock with my red lips. Courtney said this lipstick was guaranteed not to smudge and I was going to put it to the test. I reached up with my hand to wrap it around his thick cock. My red nails contrasting against it. I kissed the tip again the licked it. He tasted good and smelled like a man.

I grabbed his cock at the base and noticed he had a thick patch of dark pubic hair there. I held him as I sucked on the tip of his cock. I heard him groan. I started gradually getting more and more of him in my mouth and deeper in my throat. I estimated him to be about 7 in long but very thick. As I worked his cock he put his hand on the back of my head and I heard him say, suck my cock bitch. I put both of my hands on his ass as he drove his cock down my throat. He called me a bitch again and then a whore. It actually turned me on to hear that. He was now in full control over this situation and me. He told me to play with his balls which I did. I stoked his hairy sack and large balls. He said that it felt great and that his fucking wife never played with his balls. I drove it deep down my throat and I gagged a little. He said to gag on his cock you bitch. I felt his cock swell a little and he shuddered and started to spew his load. I had to pull his cock out of my throat in order not to choke. He filled my mouth with a large amount of his cum. I swallowed and tried to keep up. He stopped shooting and I released his softening cock from my red lips. He was breathing hard and sat down in a chair and told me to fix him a drink. I handed it to him and he told me to go into his bedroom and get ready. He was going to fuck me.

I looked at him and said, yes Sir. I turned and walked to the bedroom. I had to place a hand on the wall to steady myself. This was actually going to happen. For the first time a man was going to fuck me in the ass. My heart was racing and I felt a little dizzy. I went into the master bathroom and got a drink of water. I unzipped my leather jacket and too it off. My nipples were rock hard and sticking way out. I took off my mini skirt and then my gaff. I left my stockings and heels on. My little clit was poking out and dripped some. I hope he liked what he saw. I sat on the toilet and checked my ass. It was baby smooth and the opening was slick from the lube I had used earlier. I tried to stick a finger inside but it was very tight and hurt some. This worried me some. I hope he would be gentle.

I walked out of the bathroom into the master bedroom. He was sitting naked on the king sized bed. I stopped and set a sexy pose for him. He looked me up and down and said, damn you have some great tits. He patted the bed next to him and I sat down. He reached down and grabbed one of my tits and started sucking on it. I groaned and leaned back. He flicked the nipple and sucked hard on it. My nipples were very sensitive and he was working them. I slayed back all the way on the bed. He kept after my tits squeezing them and sucking on them. He said that mine were bigger then his wife's and she hated them played with. I felt a hand of his touch my inner thigh then travel up to my clitty and smooth sack. He rubbed me up and down just like he would if he was playing with a pussy. I could feel his hard cock pressing into my outer thigh and I knew he was ready to fuck me. He let go of my nipple with his lips and told me to get on my hands and knees.

I swallowed hard and said, yes Sir. He stood up on the floor behind me as I got on my hands and knees on the bed. He pulled my thighs back so my ass was closer to the edge of the bed. My tits were hanging down and my ass was fully exposed. He suddenly smacked my ass with an open hand. He rubbed the red hand print he put there saying, you have one fine ass bitch. He was squeezing both of my ass cheeks and would smack one then the other. It stung but it was a turn on too. I was being dominated and I loved it. He leaned down and put his face between my cheeks. He said, for a whore I smelled pretty good. He licked my asshole a few times sending shiver over my body. He rubbed his spit around it with a finger and then tried to push the finger into me. I winced and he said, that's one tight ass there bitch, I hope it's ready for my big cock. For the first time I was a little scared. I really wanted this but I was afraid of it hurting of not working. There was no turning back now.

He moved up closer behind me and rubbed the swollen head of his cock up and down my slit over my entrance. I could feel the heat from it and the size. He stopped with the head touching my entrance. I gritted my teeth and held my breath. He started to push in and my ass tightened up involuntarily. He told me to relax and to push out like I was taking a dump. I said, yes Sir and did what I was told. As he pushed in I pushed out and amazingly he started to make progress. I was still holding my breath. My asshole was on fire feeling like it was going to rip in two. I was about to say please stop when his large head popped inside me. I couldn't believe it. I took a couple of breaths then held them again because I knew he was going to push in farther. I felt every ridge and vein on his fat cock as it slide farther inside me. Halfway in he stopped and said, damn your whore's ass is tight and hot. He backed out slightly then pushed all of his cock into me. I felt the course hair at the base of his cock touch my asshole. I did it. I had a man's cock inside me. I was no longer an anal virgin.

He started moving his cock in and out of me until just the head was in me then shove his entire length deep inside me. With each stroke my ass gave up a little more of it's tightness. He had his hands on my hips for leverage as he stroked. I good feel his large sack and balls hit my puny one and I knew he was my Master. I was panting like a steam engine as he fucked me. I wondered what it would feel like when he finished and when would it happen. He was really pounding me when he suddenly pulled all the way out and told me to turn over onto my back. My ass was on fire but I did what I was told to do. He spread my legs wide open then placed his hard wet cock against my entrance and shoved it all the way in. I moaned out loud when he did that. He had his hands on my legs near my knees pushing them up and apart. He was driving deep inside me and I felt his big cock rubbing in a place that felt strange but good. I had hoped to feel some pleasure from this and at the moment I was starting to.

We were both sweating from the effort. He let go of my legs and leaned forward and grabbed my tits. I wrapped my legs around him. He was thrusting into me as he squeezed and pulled on my tits. I felt pressure building in me and I knew I could take much more. He was getting close himself. He said, take my cock bitch I know you love it. I felt something starting to rise up from deep inside me. He told me he was cumming and I felt it. I could feel his cock going off inside me. He was filling me up with his seed. He pounded into me shooting over and over. My body was shaking and spasming as he did. He pumped the last bit of his cum into me then stopped. He was above me with his eyes closed breathing hard. His cock was still inside me jerking on it's own now and then. Slowly he pushed himself off of me and pulled his cock out of me. He said, bitch you are one fine piece of ass. He then turned and said for me to go clean up some as he walked out of the room. I slowly got up off the bed and on shaky legs went back into the bathroom.

I sat on the toilet exhausted. I peed then I felt something starting to come out of my ass. I pushed a little and felt a big glob of something drop out. I looked in the toilet expecting to find blood but instead saw a big mass of white creamy stuff. It was his load. I pushed again and another large glob of his cum came out of me. He must have been saving up because this was a huge load he had put inside me. I wiped as best as I could. I probably would leak for awhile. I went to the sink to use a wash cloth. I noticed a bunch of clear gooey stuff on my lower stomach. I touched it and figured out it was cum. Not his but mine. I must have cum just as he was cumming inside me. I used the wash cloth and then went back into the bedroom to get dressed and leave. When I walked in he was in bed under the covers. He told me to get naked and crawl in bed with him at least for a little while. He then reached up and turned off the light. I unzipped my corset and took it off. I unsnapped my garters and then rolled my stockings down. I was now nude and I threw back the covers and laid in his bed. I imagine I was laying right where his wife usually sleeps. She wasn't here. I was laying next to her husband in her bed. He reached out and pulled me close. We spooned together with one of his hands wrapped around me holding my tit.

At some point I felt his hand squeezed my tit more. He held me closer and I felt his hardness pressed between my ass cheeks. I wiggled my ass a little and I felt him move more into position. I lifted one knee up to give him better access. I felt his cock against my ass from behind. He pressed it into me. There was still some of his cum leaking from me so it slid right in. I sighed from the feeling. I was sore but I loved his cock inside me. I could feel his hot breath on the back of my neck. He held my tits as he slowly stroked in and out of me. It was slow and almost gentle. He kissed my neck and my ear as he made love to me. I moaned as he pinched and pulled my nipple. It was like a dream but I knew this fucking was real. Finally he shuddered and I felt his cock spurting deep inside me. He just held it there as he dumped his load. Even when he was finished he left his cock inside me and we went back to sleep.

Something was different. I hadn't opened my eyes yet but I knew it. I blinked and saw light flooding the room. He was still behind me and amazingly his semi hard cock was still in my ass. We were so tired we hadn't moved. I stretched a little and yawned and he stirred. I felt him stiffen the say, Oh Shit. He rolled off of me pulling his cock out. He looked at the clock and said, OH Shit again. He jumped out of bed and told me to quickly get up. He said his wife told him she was going to be home around 9am and it was already 9:10 am. He told me to grab my clothes and hurry to leave. I said I need to get dressed first. He threw me one of his t-shirts and a pair of old sweatpants. He said to wear those but please hurry. I put his clothes on and hopefully grabbed everything I had worn the night before. I headed to the front door while he looked up and down the street. As I passed him on the sidewalk I asked him when I would see him again. He was almost freaking out and just said he would call me. I got in my car as he went back inside. As I pulled away I looked back and saw a minivan pull into his driveway. Two young kids got out and then a short overweight woman did. They all went into the house. I wondered if he had time to clean up things. That was close. Would he call me? Or was I a one night stand?