This is a true story.
This is the story of how I became Jennifer.
I’m not going to give my full history in this story, that is for another time. But I do need to give a little background information for you. I’ve been cross dressing for years, going through all the usual purges. Then about 10 years ago I decided to embrace the dressing. I was approaching 50 and I decided I wanted to really explore my sexuality.
The situation arose where my wife was working away a lot so I decided to grab the opportunities when I could. I dressed as often as I could and I signed up for various dating sites. It was via one of these that I met Scott. He wanted me to come over and I’d offered to dress as his wife. This is that story.
I’d showered and shaved, put some make up and my black suede heels into a bag and jumped in to my car. I parked near his house and knocked on his door. Scott opened the door and it was nice to see a quite tall lean man in his mid-40s. He was clean shaven with a shaved head and good-looking. He invited me in and ask if I’d like a drink. I just wanted some water. He explained that he was in a sexless marriage and his wife did not know he was bisexual. We chatted in the chat room and I knew what he wanted. He took me upstairs and showed me into a spare bedroom. On the bed was some clothes and underwear, obviously his wife’s. I asked him to give me about 15 minutes to get ready. I stripped off my male clothes and started to sort through the clothes he’d left on the bed. There were some nice lacy knickers and matching bra in black. There were some black lace top hold-ups. There was some other underwear in white but I thought the black would go with my black heels. I put the bra and knickers on, the bra was little tight but I stuffed some tights into the cups. I sat on the edge of the bed and rolled the hold-ups up my legs. On the bed was also a couple of skirts and some blouses. I picked a skirt that was just above knee length and slightly pleated. To finish there was a dark shocking pink silky type blouse, I put this on. The heels finished everything off.
I didn’t have a wig but at the time my hair was quite long and wavy. I quickly applied some make up, eyeliner, some purple brown eyeshadow and a matching lipstick. I was not very good at make up, and I still am not, but I think it had the right effect. I checked myself in the mirror and walked back to the main bedroom were Scott said he would be waiting for me. He was sitting on the edge of the bed as I walked in. I thought there was a problem because he didn’t say anything, but he stood up and walked towards me put his hands on my waist and said “Jennifer you look stunning”. He immediately kissed me, and it was a passionate kiss, I’d never really been kissed like that before. His hands went around my waist and pulled me closer. I could feel his hardness in his trousers, this was the most excited I had ever been in my life. I broke away from the kiss, pushed him away very slightly so that I could put my hand on his cock through his trousers. It felt big, certainly bigger than I’d ever felt before (as well as being very excited I was also a little bit scared, my heart was racing).
In the chat room he told me that his wife, Jennifer, had not sucked his cock for years. I looked him in the eyes, with my hand on his cock, and asked if he’d like it sucked. He just nodded slightly. I kissed him lightly on the lips and then slowly got on my knees. I unbuckled his belt and unzipped his jeans and pulled his trousers down. In his pants was an outline of a large cock, and I was desperate to suck it. I looked up at him and slowly peeled down the waistline of his pants. His cock popped out. It was about 7 inches, quite thick, uncut, and he was very closely trimmed. It was gorgeous. I took his balls in one hand and opened my mouth and engulfed the top of his cock. It quickly started to grow in my mouth and with my tongue and lips I eased his foreskin back. I really started to suck on his cock head. I was in heaven, with my eyes closed his heavy balls in my hand and this beautiful cock in my mouth. I heard him say “you have such a beautiful mouth Jennifer, it’s the best blow job I’ve ever had”. I loved being called Jennifer, I wanted to be his wife, I wanted to be better than his wife. He put his hands on the side of my head and started to thrust his cock in and out of my mouth, I just made sure my lips stayed clamped to his cock. He started to thrust faster and I wanted to make sure he didn’t cum in my mouth (I love a man cumming in my mouth but I wanted him inside me). He obviously felt the same, because all of a sudden he stopped thrusting, pulled his cock out of my mouth, and pulled me to my feet. He kissed me briefly, looked to my eyes and said “Jennifer I really need to fuck you”. I just said, “yes please”.
He kicked off his jeans and pants, went into the bedside drawer and pulled out a condom and some lube. My heart was racing but I so wanted this. I watched as he tore open the condom packet and rolled it on to his cock, I reached forward stroked his cock while he was doing it. He handed me the lube and I squeezed some in to my hand and stroked his cock. A lifted my skirt, put my lubed fingers into my knickers and made sure my pussy was well lubricated. I could hear him breathing heavy (and I think some of that heavy breathing was mine). He came towards me and kissed me briefly, then turned me around and pushed me onto my knees on the edge of the bed. Everything was going very quickly now. He was standing right behind me his hands on my hips. He lifted the hem of my skirt and flipped it up my back. The cool air on the tops of my thighs felt amazing, my heart was in my mouth. He pulled my knickers down just to my thighs, revealing my pussy (of course they weren’t my knickers they were his wife’s, but right then I was his wife. I was on my knees doing my wifey duties).
He put his sheathed cock against my tight hole and started to push. Luckily for some days previously I had been using my butt plug. He pushed past my hole and was up against some tightness. It was painful, but I wanted him and I knew I could take him. He could feel something was wrong and asked “are you okay Jennifer, I really need this”. I looked back at him, as much as I could, and said “so do I Scott, go gentle to start”. He pushed a little harder, I took a deep breath and then he was in me. He pushed his full-length into me, it was fantastic. It took my breath away slightly which he heard, and said “is that okay Jennifer?”, I replied “fuck me, fuck me like you want to fuck your wife’s arse”. And he did. Quickly I ended up on my stomach with my legs spread apart his full weight on me, he only stopped briefly to pull off my knickers. He was really pounding my arse and it felt amazing. He was lying full-length on top of me, breathing heavily in my ear, kissing and licking my neck. I didn’t think it could get any better. He was really pushing hard into me, long strokes, and I could feel his balls slapping against me. I wanted it to last forever, but I think you can imagine it didn’t! Scott had said he was in a sexless marriage, and I think I may have been the first fuck he had had for a long time. I was hoping for sex in lots of positions but that was never going to happen. He started breathing more heavily and thrusting harder. Then suddenly he pushed really deep into me and groaned in my ear “I’m cumming”. I would love to say that I felt him pulsing in me, but I didn’t. He did a few short sharp strokes and then collapsed on my back. I felt like a real wife, having done my duty for my husband.
He stayed hard for a short while and then he pulled out of me and lay on the bed beside me. As you girls will know there is a warm glow that you can feel deep inside you after you’ve been arse fucked hard. And I felt that glow. I hardly moved, staying facedown, legs spread, my skirt up against my back. Scott started to move and I was hoping that I could peel off the condom and suck him clean, but I think he was already feeling guilty. I rolled over onto my back and sat on the edge of the bed. He had disposed of the condom and was pulling his pants and jeans on. I looked at him and I understood what I should be doing. I got up, walked past him into the spare room. The feeling of walking even just that short distance without my knickers felt wonderful. I quickly changed out of his wife’s clothes, wiped my face with a cleansing tissue and put my clothes on.
By the time I walked out of the small bedroom I could hear he was downstairs. I had my bag and walked downstairs. He was at the bottom of the stairs by the front door, as I walk past him he said very sheepishly “thank you”. I replied “my pleasure”. With that I walked out of the door and back to my car.
I drove home and cleaned the make-up off properly. I then went to my bedroom put on a pair of knickers and wanked myself whilst fingering my sore pussy. I came very hard. My one regret was that I didn’t steal his wife’s knickers, as that would have been a wonderful memento.
That was the story of how I became Jennifer. It is completely true and I hope you’ve enjoyed it. Please comment if you liked it. |
