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#Exhibitionist #Gay #Trans #Virgin
By Neverender
The older I got, the more curious I became.
My cousin Josh had unlocked something inside of me that weekend. I was terrified at first but my curiosity ended up taking over and I gave Josh two blow jobs that weekend.
The following weekend we did it all over again. This time we didn’t bring our fishing poles. We spent and entire weekend swimming naked in our new favorite place and exchanging blowjobs in our tent at night.
We did that a couple more times before the summer ended and then it quickly fizzled out. I see Josh a couple times a year nowadays and sometimes when it’s just the two of us and we’ve had some alcohol we get into talking about it but neither of us has shown any interest in rekindling our tent play.
In high school I met a guy and found out he was gay. Him and I fooled around a number of times but nothing ever came of it. We would suck each other off once or twice a week for a few months. Once he mentioned he wanted me to fuck him in the ass because he had never tried it. Neither had I but I wasn’t going to say no if he really wanted it. I was so horny at 16 I would’ve stuck my dick in a meat grinder if it looked my way. I barely pressed my dick against his hole and he said it hurt and chickened out. After that, we hardly spoke and it also fizzled out.
By 18 I still very much considered myself heteroual. I hadn’t had with a man, I just enjoyed sucking dick once in a while. I was however heavily into cross dressing. I had swiped a number items from my mother’s closet that she never wore. Various bras and panties, a few pieces of lingerie, some stockings and even some jewelry and makeup. Eventually I began going to thrift stores to find some cheap clothing. I was far too scared to go to a local mall in case someone saw me.
My mom was working nights at this point and I had the entire house to myself. As soon as she would leave I’d get dressed and parade around the house. It would always end in me masturbating in mom’s bed or in the shower.
When I was 19 I went off to college. It was my first extended time in the big city. I got a job at a small record shop in a very liberal part of town. I felt incredibly comfortable in that environment.
One day this older man came into the shop and we talked music for a half hour before he bought some records and left. The next day he came back, and the day after that he came back a third time. Each time we chatted about music and various songs we liked.
After the third time he had come in, I drove the hour and a half back to my mom’s house. In my dorm it was very hard to do any sort of cross dressing. My roommate wasn’t cool. The only thing I brought to my dorm was panties that I would wear every day underneath my boxer shorts. So, aside from missing my mother and the relationship her and I had started, I regularly found myself just craving being in women’s clothing. I’d do in my room, dress up and just lay in bed. It was very relaxing and comforting. I also really missed my mom.
Mom and I ended up making love that night. You can read all about that relationship and how it happened in my previous stories. Once I fell asleep I slept like a baby. I slept so well that I had a very vivid dream. The dream…?
I was wearing a lingerie piece that I didn’t recognize and some black stockings and high heels. I had long red hair and boobs! The man that kept coming to the record store was me.. very aggressively.. and I was loving it! I woke up around 3am sweating, out of breath and my dick was harder than it had ever been. As I began to try and remember my dream I realized that this man was the first time I had ever been attracted to a man.
The next time I worked he didn’t come by and I went back to my dorm disappointed. The next day he didn’t come by either. I laid in bed that night feeling things I had never felt before. I was really into this man and I had no idea why.
The next week I was walking the half mile to work and to my surprise I ran into him! He asked if I was headed to work and then asked if he could walk with me.
My heart pounded and I could barely breathe the entire walk. I finally found out his name was John. As we got to my work, John asked if I wanted to hang out sometime. I was really confused what he meant by “hang out”. Did he just want to hang out or was this a date kind of thing? I didn’t know!
That Friday John came and picked me up at my dorm. When I met him outside my dorm my heart began to pound again and those feelings of confusion washed over me and I almost considered turning and leaving.
John was 31, which was a little old for 19 year old me, but I tried not to get too hung up on it. He was 6’2” and athletic looking. It surprised me that he was interested in me since I was gaining more and more weight the older I got. By 19 I was up to 280 lbs and me not feeling like I was his “type” was the one thing going through my head reminding me to calm down. John was also wearing a suit which I hadn’t seen him in before. Each time I had seen him at the store he was in a t shirt and jeans.
John placed his hand on my upper arm as he greeted me which I had to figure out if it was a signal or not. We got into his car which was a big SUV. We talked and laughed about who knows what and talked quietly throughout the movie. When John dropped me off we parked and talked a little more.
John suddenly leaned forward and kissed me. I was shocked at first but I didn’t push him away. We ended up making out for a solid 23 minutes before John grabbed my hand and placed it on his rock hard cock that he had magically pulled out. He was so hard! His cock was at least 8”!
I slowly stroked his cock as we continued to make out. The thought that even though we were in a very dark unlit parking lot, and it was highly unlikely but the thought that someone could be watching us turned me on so much!
“I only live about a mile from here if you wanna go back to my place.” John said
I thought about it for a few seconds and I’m pretty sure I knew what he meant and I knew I wasn’t ready for anal yet. I had never had more than one curious finger in there.
“I’m definitely not ready for that just yet, but I can still take care of this.” I explained referring to his throbbing cock.
John reclined his seat and tugged his pants down enough to fully release that big hog of his. I turned towards him and put my head in his lap. His cock felt even thicker in my mouth! John grabbed a handful of my red hair and moved my head up and down along his cock. Each time he pushed down he let out a little moan.
“Goddamn this feels good!” He muttered
As he let go of my hair I began to really get into it. There was something eerily y about the smell of his balls. They were definitely clean but they had a salty smell to them like he had just been to the gym before we met up. So with my hand I reached down and grabbed his balls and started licking and sucking them. John flinched a bit like it tickled. I continued to go back and forth between his balls and his thick dick.
Once again John grabbed my hair and pushed my head down and held it there. I gagged a bit but I managed. Then his hot cum hit the back of my throat. He was cumming like he hadn’t cum in a month. Shot after shot of hot cum squirted into my mouth. I swallowed as much as I could but I felt a bit of it dripping down my chin.
John released his grip on my hair and I popped up. Swallowing the last of his cum I wiped my chin and licked it off my fingers.
“That was amazing!” John said “..thanks.” He finished
“You don’t have to thank me. I liked it.!” I confessed
John and I agreed to go out the next weekend. I was really excited to go out with him again and as the week progressed I began thinking about the first date. He wanted ofcourse. I wanted it as well but I was scared. Him having an 8” dick didn’t help that either.
Our date was Saturday night and on Thursday night leading up to that I went back to my mom’s house. I told her I had no classes Friday and she agreed to skip work so we could have a night together. But for now she had to go to work, which is exactly why I was there. I wanted the house to myself and I had a plan.
I dressed myself up in one of mom’s pieces of lingerie she wears for me. I went all out this night. Makeup, jewelry.. everything. My plan? I was going to use my mom’s dildo on my ass and see what it’s like.
I did my usual parading around the house like a housewife doing chores, and after an hour of working up the nerve to do this, I finally committed to it. I raced to mom’s bedroom and dug through her underwear drawer. She had 2 dildos and a vibrator. I held all three and the one that felt the most like John was an 8” thick dildo with a suction cup on the base.
I went in the bathroom, removed all my clothes and got in the shower. After a few minutes of using a finger or two I finally stuck the dildo to the shower wall at about the right height. I squirted some lotion on it and my asshole. I turned around, reached back, bent over and pressed the dildo to my ass and gently pushed back. It hurt! I tried a second time going a little deeper. Pulled back still hurts but hopeful. I tried a third time and this time the head of her dildo slipped inside my ass.
“Holy shit!” I yelled through clinched teeth
I began to slowly inch it in and out. It still hurt but it was getting easier. I started to play with my dick as I work my ass. It was getting easier and deeper with each push. And it felt intense and amazing! It didn’t take long before I had shot cum all over the bath tub.
Suddenly the bathroom door swung open! I looked up frightened standing straight up. The dildo flipped out of my ass so fast that it fell off the wall and rattled around the tub. It was my mom!
I stood there stunned. Both of us speechless. There was a pile of her clothes on the floor and I’m wearing her earrings and makeup.
“I don’t even know what to say.” She finally broke the silence
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By Neverender
#Exhibitionist #Gay #Trans #Virgin
