My Secret Relationship Part 3

I found out how much I enjoyed sucking J’s dick and having him suck mine as well. I wasn’t expecting it to go where it went next though.

All the while J and I had been fooling around with each other, it just seemed like two really horny boys just doing what they needed to do to get their rocks off. It felt like a form of masturbation rather than any kind of homosexuality. However, when we began giving each other oral sex, and then realized how much we loved it, thoughts that we might be gay, or at least bisexual started creeping into our heads.

We both handled it differently to say the least. J was proud and macho and still rationalizing it as a form of masturbation and I however took a different route. I slowly began to embrace the idea that I liked men and women.

Right around the same time J and I discovered oral sex, I began noticing I was constantly horny. Everyone and every thing turned me on. Any thing I could do to give myself the pleasure or the illusion of sex was fair game as far as I was concerned. And that is what lead to me cross dressing. I have never told anyone about this other than J and just typing that felt unsettling.

One day during summer vacation when I was 14, I was so horny that I decided to snoop through my moms closet and dresser drawers. I just wanted to see a bra or a pair of panties and I didn’t care if it was my mom’s. Truthfully, had my mom offered at this time in my life, I would’ve had sex with her without hesitation.

In my snooping I found what I expected. Bras, panties, nightgowns and even a couple pieces of lingerie. I had seen my mom’s underwear and nightgowns before but I had no idea she had sexy lingerie. My dad had left us when I was 10 and she hadn’t, at least to my knowledge, been with a man since. I kept digging through her drawers and found she had a vibrator and a dildo. That turned me on like you wouldn’t believe. I thought about J’s dick and then I thought about how this dildo had been inside my mom and I immediately started sucking it and jacking off.

When I finished, I kept snooping in her closet. Inside I found a box of bras, panties and lingerie. As I began to pull it out to look at it, I noticed it was smaller than the other page had in her drawer. Mom had put on some weight since my dad left and I guess this stuff in the box was old and didn’t fit anymore. Not sure what made me so curious about it but I began trying all of it on. I really, REALLY liked the way the silk and lace stuff felt against my skin. It was a feeling I hadn’t felt before. I began modeling all of it in the mirror and just kept getting more and more intrigued and excited. I had to get moms dildo out again and masturbate.. again!

This time I had sexy lingerie on and I pretended I was sucking J’s cock and I had an incredibly intense orgasm. When I was done, I cleaned up, put everything back but found myself back in there masturbating again less than a half hour later. I couldn’t stop! I was instantly hooked. So I took a couple of the things from that box and began sleeping in them almost every night.

I went over to J’s and I really wanted to tell him about it but I didn’t. I was definitely scared. Even after everything we had done over the last 4 or 5 years, it still scared me to bring it up.

That night we were, as usual, naked and kissing in his bed and as he got into position to suck my dick, I asked him to suck and play with my nipples first. He agreed as I think he liked it almost as much as I had grown to. While he was on top of me all I could think about was how I wanted him to fuck me. I had never had that thought before. Suddenly I couldn’t get it out of my head. I wanted his dick inside me so bad! I was far too scared to tell him that night.

This went on for about a year without me telling him. A few times we casually talked about someday we should try anal sex but it was so casual and it seemed like it wasn’t going to happen.

Finally, I had had enough… I had just turned 16 and J was turning 17 and I decided I was going to bring it up seriously.

When I was 14 I started gaining weight. I wasn’t super overweight but I was turning into a husky guy. With that I began getting man boobs. Most guys would probably not want man boobs but I really enjoyed J playing and sucking my nipples so I kind of liked it. By the time I was 16 I could wear a B cup bra.

J’s 17th birthday, I stayed at his house as I usually did on most weekends. That night we got into bed and instantly started making out and groping each other. J would regularly play with my “tits” now and I loved it! I had never been anything close nor have I ever been anything that resembles feminine except when I was around J. Something about him just sent me to places in my mind that no one has ever done to me before. I wanted to be his woman so badly! I would’ve done anything for him at this point!

J climbed on top of me in a missionary position and continued licking my nipples. I felt his dick swinging back and forth gently touching mine. His dick had grown so much since we started this as kids. He was a solid 8” and nice girth too. Each time I felt his dick brush against mine I bit my lip trying not to cum. I slowly reached up and began caressing his arms and his muscles made me lose it. I shot cum all over my stomach!

“What happened?” J asked

“I’m so turned on right now! I couldn’t stop myself.” I answered

“Wow!” J laughed

“I want you to fuck me!” I whispered “…for real. I want you t inside me.” I eagerly added

“Really?!” J said looking down at me

“Mmhmm.” I moaned back

I spit in my hand and began rubbing it all over his cock, then lifted my legs up and pressed his dick against my hole. J pressed and pushed and after 30 seconds or so the tip of his dick slid into my ass. I bit my lip so I wouldn’t scream. It hurt like hell! Thinking I made the worst decision of my life, I asked him to take it out. He did not. Instead he gently thrusted a few times and it hurt and hurt and hurt. Had I not also kind of liked it, I would’ve been more assertive about stopping. Within 30 seconds though, J started cumming inside me. As he pulled his dick out of my ass, I moaned in pain and pleasure. I could feel his cum dribbling from my hole.

J was very apologetic and I wasn’t mad. I would’ve done the same thing in is position.

“Are you ok?” He asked

“It hurt really bad, but maybe we did it wrong.” I answered

“Well, for what it’s worth, I really liked it!” J said as he kissed me.

“I kind of liked it too but I want to know how to do it right so it doesn’t hurt so bad before we try it again.” I explained

J agreed and we went to sleep. The next morning we exchanged blow jobs and I went home determined to figure this out!

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