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My cousin is a trap

My cousin Joey is 16 and recently came out as transsexual. I think everyone else knew it years before he did, or at least before he accepted it. Joey, now Jennifer, has always been super feminine with long blond hair, a very feminine face, and a slim asexual body. Not that she's on hormone treatments her breasts have started to bud and her hips thicken. Add in a complete revision of her closet to go from guy stuff to dresses and the addition of some makeup classes and the best from Ultra and Jennifer is more of a woman than Joey ever was a boy.

Fast forward to this past weekend. Jennifer's parents went on a trip to Boston for shopping and left Jennifer with my mom and I. In the past we would just share a bed, but now that she's Jennifer she got the guest bedroom, which is right next to mine.

That first night all three of us sat up front and watched The Accountant. Mom was in her usually sweat pants and old t-shirt, I was in shorts and a t-shirt, and Jennifer had on a very sheer set of PJs. After the movie mom went to bed and we sat up to watch another movie, Ouija The Beginning.

First off, the movie sucks, but more importantly Jennifer ended up getting scared and sat next to me on the couch. My mom keeps the temp down and we got a bit cold so we covered up with a throw blanket. There's a scene in the movie where the older sister takes her boyfriend up to her bedroom and tells her sister to watch tv. They were kissing on tv when Jennifer turned to me and said she's never been kissed before. I was a bit shocked. I knew she had only recently come out, but I also knew that she had dated girls for a bit when she was still Joey.

I told her she would soon, when she found the right guy. But I knew it was going to be very difficult for her to find anyone in our small town, with their small minds. We talked a bit more and I told her if we weren't cousins I would ask her out and certainly kiss her. The movie was an unfortunate trainwreck and we ended up giving up and going to bed.

I was in my room about five minutes when the door opened and Jennifer asked if she could come in. She sat on the side of my bed and asked me if I meant what I said about taking her out on a date and kissing her. I told her I did, and she leaned forward and kissed me gently on the lips. I kissed her back, and slowly slipped my tongue into her mouth. The kiss depended and Jennifer leaned forward until she was laying right across my chest. I pulled back the comforter and pulled her to me as I rolled onto my side.

We lay there together for some time just kissing before I felt her hand slide down my side and cup my cock. I hadn't even realized it had become erect, but when she touched me it was like lightning shooting through me. Her stroking got to me, and I mentioned I was getting close to cumming. She broke the kiss and slide down my body, taking the head of my cock into her mouth just as my orgasm overwhelmed me. When I was done she licked and sucked my cock and her hands clean, whispered thank you in my ear, and left my room.

The next day I didn't know what to think or say. Luckily, my mom decided to take Jennifer into town grocery shopping and I was out for work when they came home so we didn't end up talking until later Saturday night. That evening we ended up watching TV again and mom went to bed at nine as she had the morning shift Sunday at the hospital. I tried to apologize for what I had done Friday night and Jennifer just laughed, telling me I didn't DO anything, she had done it all. We laughed a bit about that.

By 10pm we were both pretty tired so we shut off the tv and went to bed. Like the previous night I had just settled into bed when the door opened and Jennifer came in. I tried to speak, but she kissed me and said she wanted more and immediately pulled back the covers. My cock was already hard when her mouth closed over the head. I twas amazing, the feeling of her mouth on me, the sight of her. She sucked and stroked my cock for a few minutes before she stopped and sat up. She said she wanted more tonight and asked if I was willing to be her first. Like an idiot I asked first what? She just smiled and said she wanted me to be her first fuck.

I didn't know if she meant she wanted to fuck me, which I wasn't interested in or for me to fuck her. Jennifer answered my question by crawling into my bed on her hands and knees and presenting her ass to me. She handed me a small jar of Vaseline and told me to lube her pussy up good and to go easy because I was much bigger than her vibrator.

She had worn a frilly teddy that was pulled right up to her waist, leaving her smooth ass bare. I don't think I ever noticed just how feminine Jennifer looked, but from that angle she was just as much a woman as any other girl I've ever seen in real life or magazine. I applied some of the Vaseline to her puckered hole and rubbed a bit into the head of my cock for insurance, positioned myself at her opening and slowly pushed forward.

You can't imagine how hot and tight Jennifer's pussy/ass was. I grabbed her hips and slowly slid into her. I was about halfway in when she arched her back and moaned. I stopped, thinking I'd hurt her, but she turned her head and told me it felt better than she had imagined and to keep going, so I pushed forward until I was fully sheathed.

I tried to fuck her slowly, to give her time to get used to me, but it was just too much. She was too beautiful, too tight, I was too excited, and it was just too new an experience. I realized too late that I was fucking her hard, pulling her hips towards me as I stroked deep inside her. The bed was rocking and creaking with my thrusts, the headboard banging on the wall, and she was pretty vocal telling me she loved me, telling me how good I felt inside her, telling me she wanted me to fill her with my cum.

Like the previous night I was suddenly overwhelmed and cumming inside her, pulling her hips tight against me as my cock pulsed with each shot. Meanwhile she cock began to spurt as well, coating my sheets with her thin fluid. It was at that moment that my mother pushed the door open, a flood of light coming across our bodies.

Next Confession

A MUCH older woman

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      • Oh god shit hit the fan

      • Awesome! What did your mom say?! Loved that story

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