When I was 18 my family found out we had a whole other side of the family that we didn’t previously know about.
I met some second and third cousins and aunts and uncles that I never knew we had.
One second cousin I met became really close with me. Taylor. She was 19 and I was 18 when we first met. A year after I met her she finally felt comfortable telling me she is trans. I was shocked only because the whole year that we became close, I had no idea. She was a beautiful petite girl with long blonde hair.
Taylor came out to me and was worried about how I would react. I told her I still loved her and it didnt change a thing. As time went on Taylor got a boob job and continued taking her testosterone blockers and she’s still one of the most beautiful women I know.
She went on a date with a guy one day and it went horribly wrong. She called me to pick her up and she cried and vented to me all about it. She asked if she could stay with me that night. I thought nothing of it aside from her wanting some comfort from someone who accepted her. We had a few drinks and talked as we sat on the couch and we fell asleep together.
I woke up to her head on my chest and my arm around her. I really felt nothing sexual towards her. I was just glad that we just had someone to go to when things were tough.
I looked down at her and didn’t want to wake her so I closed my eyes and fell back asleep. I woke up to a soft pair of lips kissing my lips. In my half asleep state I kissed back, it felt like a dream. I opened my eyes and Taylor was looking up at me, biting her bottom lip and gazing into my eyes in such a way that made me feel butterflies in my stomach. I leaned my head towards her and we kissed again and I said, “What are we doing?”
She replied, “Do you like it?”
I hesitated, “Of course I do, your lips are so soft and you’re very beautiful but… isn’t this wrong?”
“It doesn’t feel wrong to me. I want to keep kissing you. I want you to make love to me.”
I didnt have any more words. I don’t think anyone has ever looked at me that way. I leaned forward and we kept kissing. She began rubbing her hand between my legs as I quickly became harder than ever. She let out a moan and gently bit my lower lip as we kept kissing.
She reached her hand under my shorts and boxers and rubbed my cock with her palm and moved it upwards so half of my cock was sticking out of my waistband.
It wasn’t long before she stood and led me by my hand to my room. She directed me, “Take your clothes off and sit on the edge of your bed.”
So I did. I sat there with a full erection as I watched her take her shirt off and then her bra, revealing her large perky tits. She pushed her jeans down on each side as she slowly shook her hips back and forth.
I obviously knew she was a pre op trans girl so I just anticipated what came next. She wore a pair of pink cotton panties and I could see the shape of her head imprinting from the inside of her panties. She was getting hard. I could see part of her balls trying to escape the side of her panties as she slid her pants down to the floor. She finally stood straight up in nothing but her underwear, “What do you think?”
“Taylor, youre beautiful. You always have been. I want to see all of you.”
She grinned and it almost looked like she could cry. She slid her panties down revealing her cock. It hung forward, average sized and half erect. As I stared she told me, “I cant always get super hard anymore. It’s the… you know the feminine stuff I take to stay pretty,” she blushed at her silly explanation.
She stood there looking all cute for a second before she kneeled down in front of me and started giving me a blowjob, “you’ve already got pre cum coming out,” she chuckled.
“Well yeah, this is pretty fucking hott,” I replied.
I leaned back and just enjoyed the show. I had to mentally stop myself from wanting to come too early. Her voice saying, “I want you to make love to me,” just repeated in my head.
I reached down and gently grabbed her on each side of her face. She followed my lead and stood into me, falling on top of me as we kissed more, naked on my bed.
I suddenly noticed her cock rubbing against my leg. I felt a wet spot and knew that she now had some pre cum coming out of her. I stopped kissing her and reached down to touch the head of her cock, feeling the sticky liquid, “Hmm, pre cum already?”
I smiled and we both chuckled. She kissed me again and then said, “I know you have lube in here you little horn dog. Go get it,” she rolled off of me onto her back.
I got off my bed and made my way to the bathroom. I opened the medicine cabinet and grabbed my lube that I was so used to just masturbating with. She said, “Put some in my hand and then put a lot on your dick.”
I followed her instructions. She reached her lubed fingers between her legs and rubbed it on her ass. I spread my lube evenly on my cock and she directed me more, “I want you to fuck me. Be gentle. Go slow.”
I approached her ass and she put her ankles up on my shoulders. She reached her lubricated hand between her legs and grabbed my cock, guiding it to her ass. I gently pressed the tip in and very slowly made my way into her. She told me when to go more and when to slow down.
Eventually the lube was all over and I was pounding her ass and she loved it. She moaned and told me to go harder and deeper. Over and over my thighs slammed into her ass cheeks. I knew I was more than half way to finishing. I slowed my strokes down and reached for the lube on the side table. I squeezed some into my right hand and continued fucking her. I reached down and grabbed her cock. She may have had trouble getting completely hard sometimes
but this wasn’t one of those times. She felt like a smooth steel rod in my hand. She moaned louder and louder. I told her, “Babe you are so fucking hard. Youre so fucking sexy Taylor.”
We continued for a few more minutes. I told her I was about to come and she told me to come inside her. After I came she told me to stay in her ass while I stroked her. A few seconds later she said, “Im gonna cum. Oh yeah baby I’m gonna cum.”
She shot 5 or 6 strings of cum onto herself. A couple shots hitting her tits. The last couple shots dripped down my fingers and I felt like I could cum again. We just stayed in that position for a minute, breathing heavily and sweating. I pulled out of her and she leaned up and pulled me to her and we kissed again.
We showered together and I made us breakfast that morning and we talked about it and we both knew this wasn’t gonna be a relationship but we were both open to having fun again. Specially after I was brave enough to tell her I wouldn’t mind seeing if I liked giving her a blowjob. After that she said, “I should go soon before I get too horny.”
And that was just the first time Taylor and I hooked up.