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The Anatomy of a Freak: Pt II

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This is the true story of my first time sucking a dick.

I had just turned 16 and despite never actually having a girlfriend and yes, being a virgin still, I knew a lot about sex. I learned at the age of 9 that I got off to watching my parents fuck. I had a great run of that for about 3 years until my dad left us when I was 12.

I still would snoop around my mothers dresser drawers almost everyday. It wasn’t as much about finding something anymore, I had seen everything she had, but it was more about just snooping thru her panties and lingerie drawer. The act itself I guess.

Not long after my dad walked out on us, I started getting bigger. Puberty was in full effect now and it was doing me well. I was thin, but very toned from playing sports. My cock had grown considerably as well!

What also came shortly after my dad left was not only was I snooping thru my moms drawers, I started wearing her clothes as well. Now that I was older and had grown up, the fit much better. It started with just wearing her lingerie when I would masturbate. That progressed to wearing her bras and panties. Then I’d wear her stockings and pantyhose. And eventually I would start trying on her everyday clothes.

I felt unbelievably comfortable in my mothers clothes. They smelled like her for starters which made me feel good but there was also a sense on comfort I had never experienced in my boys clothing.

It may come as no shock that I was the weird kid in school. Despite playing and excelling in athletics, I still was the poor kid that everyone made fun of. So, in an attempt to feel a little more comfortable and safe, one day I decided to wear a pair of my moms panties to school. They were a silk white pair, nothing special. I put a pair of my boxer shorts over them so no one would accidentally see them. All day, anytime I felt sad or uncomfortable, I just thought about how nice the silk felt on my cock and balls.

It wasn’t long after that, I was wearing panties and a pair of nylons. As long as I wore jeans and socks, no one would see anything right?

One day after school, I was walking home alone. I had already made plans to jackoff as soon as I walked in the door. However, I was stopped by a kid that lived next door to me, Jordan. He was 2 years older than I was and he was more or less the cool kid on our street. We had played football together a few times but never had any interactions beyond that. Our conversation lasted well past when we made it to our houses. We just stood in my driveway and talked for almost an hour.

Jordan asked me if I wanted to see something cool at his house. I reluctantly agreed. Despite wanting to get home and crank one out before my mom got home from work, Jordan was rather popular and I thought maybe it’d help me out a bit at school.

We got inside and went upstairs to his bedroom where he lifted his mattress and showed me a Penthouse magazine. I had seen plenty of these before, hell I had swiped a few from my uncles and had them stashed under my mattress but I was still excited to see pornography.

We looked thru the pages together for a few minutes before Jordan pulled out another magazine for him. I was lost in a trance of girls with gigantic tits that I didn’t even realize, Jordan was laying on his bed with his dick out stroking it.

“Dude, what are you doing?!” I asked him

“Wanna join me?” He boldly answered

The truth, hell yes I wanted to join him! I had laid out some of my favorite clothes my mom had, and wore a pair of her panties and nylons to school. I had been horny as fuck since I woke up and if I wasn’t still wearing those panties and nylons, I’d have done anything Jordan wanted to at that moment. Anything!

I resisted temptation to join him but he got upset and even a bit pushy. Jordan even started getting grabby. As he was reaching for my jeans to unbutton them, I pushed his hand away. He reached for it again and instead grabbed my cock.

“See, you’re just as hard as I am!” Jordan said rubbing my bulge a bit. “Take that thing out and have some fun.” He added

I had given up on pushing his hand away, besides it was the closest thing to a hand job I had ever gotten. I had given up so much that I didn’t notice him unbuttoning my jeans. When he opened them up, he saw a quick glimpse of my panties I was wearing.

“Dude, are you a cross dresser?” He asked stunned

“I gotta go!” I muttered as I buttoned my fly and stormed out knowing that my life was over.

The next day nothing happened at school and I was starting to relax a bit. Jordan approached me in the lunch room and asked if I wanted to hang out after school. He said he wanted to talk to me about something. I agreed in the hopes that if I was nice to him he wouldn’t tell the whole school about my fetish.

Jordan once again walked home with me. We didn’t speak to much and when we did, it was about sports or homework. We got to my house and he asked if he could come inside. I said yes.

“Ok, first thing I gotta know.. I swear it doesn’t leave this room. Are you wearing women’s clothes?” He asked as we sat on the couch.

“*sigh* not right now I’m not.” I said in shock that I even gave that much information.

I went on to give him the short explanation on why I wore them. In retrospect I suppose there isn’t really a way to spin it that doesn’t sound weird to a 17 year old guy.

“So.. are you like.. gay then?” He asked uncomfortably

“No.. I don’t know.. I like girls.. I don’t know, maybe.” I answered confused about the situation.

I couldn’t believe I was just blurting out all this private stuff about me. I didn’t know what to do next.

“Ok..” Jordan said before taking a deep breath and exhaling. “I’m gay.” He then said quietly while looking down at his feet.

“Wow.” I answered “I had no idea.. I mean after yesterday I kind of had suspicions, but.. yeah.. wow.”

“I don’t know what to do.” He said

“What do you mean? There’s nothing wrong with it.” You like what you like man.” I explained. “I can’t believe I’m saying this but, I used to jackoff while spying on my parents fucking. That’s probably weirder than anything you got.”

We sat and talked for about 45 minutes and he kind of spilled his guts to me which at first I thought was weird since we barely knew each other but as it went on, I realized I was probably the first person he had ever talked about this to.

“So, you really like to wear women’s clothes?” He asked as our conversation settled

“Yeah. It’s unbelievably relaxing to me.” I answered. “Wanna see me dressed up?” I asked and then immediately regretted it.

“Sure!” Jordan replied which then made me regret asking.

I told him to wait in the living room while I went and did my thing. I knew my mom would be him in a little more than an hour so I assumed I had time. I went into my mom’s room and pulled out a pair of blue lace panties. I picked them in particular because they had a matching bra that had some padding when I wore it, I looked like I had tiny tits.

As I began to rummage thru my mom’s drawer looking for stockings or nylons to wear, I began to wonder why Jordan just came out to me. He did seem eager to see me in women’s clothes. Hmmm, was he into me? Of course he was. Ok, maybe he wasn’t but I’m the closest thing to another gay guy he’s been around so maybe that’s why he’s spewing out all his stuff. I found a pair of nylons that I liked wearing. They were a few shades darker than my skin tone so they made my legs look tanned. My mom must’ve been wearing the high heels of hers that I liked because they were not around so I had to go without shoes. I slipped my favorite nightgown my mom has on over my head. A red silk night shirt with black lace around the neck. It was just long enough to reach the the part of my thigh where the nylons stopped.

“Hey, go into my bedroom.” I yelled down the hall to him.

My heart was pounding so hard, I thought I was going to pass out! I couldn’t believe what I was about to do. If you had told me two hours earlier that this is what was going to happen I would’ve died of laughter.

As I heard him enter my room, I did my best to catch my breath. It didn’t work but I couldn’t keep him waiting in there so I just opened the door as fast as I could, jumped in my room , slammed the door and turned around and faced him.

The more I thought about everything, the more I thought about what I’d be willing to do if he wanted me to. In my head I thought, I guess we could masturbate with each other. Then I began to think, would I go as far as stroking his cock? Would he stroke mine? I kept going further and further in my head not knowing where he’d want to go or how far I’d actually go. The further I got in my head, the more I wanted to find out and the more I wanted to find out, the more I wanted to make some kind of sexy entrance to perhaps entice him into fooling around. What I did, was the complete opposite. I made, the single most awkward and strange entrance imaginable.

As I slammed the door and turned to face Jordan, I had my eyes closed tightly. When he didn’t say anything, I thought the worst. I was sure he thought I was weird. I bravely opened my eyes, one at a time and saw Jordan had sat up straight and was staring at my legs.

“Can I?” He asked reaching out for my thigh

“Mmhmm. They’re kind of hairy though.” I said lifting the nightgown a bit revealing the top of my nylons.

I had made the decision right then and there that I was going to do whatever he wanted me to do for him.

It wasn’t the first time I had fooled around with a boy. It wasn’t the second time either. In fact I had fooled around quite a bit with another kid I knew prior to all this but it had never gone further than us giving each other hand jobs. I already knew Jordan and I were going to get at least that far.

As his hand hit my thigh, he began to rub up and down the outer part of my leg. It felt amazing to be honest. Jordan inched forward to the edge of my bed and reached out with his other hand and started rubbing the inner part of my thigh. That sent a chill up my spine like I had never felt before and made me relax much more. He leaned over and kissed my inner thigh and that was all it took for me to be completely lost in the moment.

I grabbed Jordan’s hand and stood him up. I placed my hands on his hips, tucked my fingers under his shirt and lifted it over his head and threw it on the floor. He already had a moderately hairy chest which was hot! I started running my fingers thru his chest hair and leaned down and nibbled on his nipple for a second. Jordan moaned and giggled a bit for a second. As I looked back up, he pulled me in and kissed me. His tongue immediately began to swirl around mine. I was so turned on!

We kissed pretty heavily for a few minutes and then I just went for it. I began to unbutton his pants. As I pulled the zipper apart, I pulled away from our passionate kiss and got on my knees. I grabbed his pants and underwear and yanked them down to his ankles. His cock stared me right in the face and was already trickling out a drop or two of pre cum.

I had never sucked a dick before but truthfully, I had wanted to with the other kid I fooled around with but never had the courage to bring it up. I had shot my own cum in my mouth before so I knew what it tasted like so I wasn’t as nervous as I thought I’d be when I reached this point.

I gently squeezed the base of his shaft, stuck out my tongue and licked the tip getting that pre cum licked up. Then I ran my tongue on the underside of his 7” cock from the shaft to the tip before opening and shoving his manhood in my mouth. I immediately loved it! It was warm and hard. I smelled and tasted amazing!

Jordan let out a few quiet moans as he began to run his fingers thru my hair. Then his moans got louder and his breathing increased. It felt like his dick got harder. Then all of the sudden he shot a hot load of cum down my throat. I gagged for just a second or two, coughed then put his cock back in my mouth. He shot a couple more spurts of cum on my tongue and then squeezed his cock and drained the last few drops out. He looked extremely relaxed. Like a 500lb weight had been taken off his shoulders as he sat on the bed and laid back letting out a huge sigh of relief. I amazed myself more than I did him though I think, I swallowed every drop of cum. Well, not everyone. As I pulled his cock out to cough and swallow what I had in my mouth, he spurted a second shot on my chin that had dribbled down onto my moms nightgown.

I immediately jumped up in a frenzy and ran to the bathroom and began trying to clean up the wad of cum. This was my favorite nightgown my mom has but it was also hers. If she didn’t wear it tonight when she got home, she’d probably wear it tomorrow.

I did pretty good in cleaning up the glob of Jordan’s cum and put everything away before my mom got home. I raced back into my room not really realizing I was completely naked. Jordan still laid back on my bed, his pants around his ankles.

“Whoa!” Jordan said as he looked over at me

“What?” I asked starting to pick up my clothes

“Don’t you want to take care of that?” He said pointing at my cock which was surprisingly still hard

Jordan kicked off his pants and was now completely naked as well. He grabbed my hand and pulled me to the bed and I got between his legs. He sat up and we started kissing again. Jordan slowly started to rub my cock. Then he laid on his back and wrapped his legs around my waist. He spit in his hand and returned to stroking my dick. Within seconds I shot my own hot batch of cum all over Jordan’s stomach. He pulled me down on top of him and we started kissing again. Our cocks rubbing against each other and my puddle of cum now making a mess as our stomachs rubbed together as well.

When we finished kissing, we wiped up all the cum and got dressed. My mom was just getting home now and Jordan left. My mom called me down for dinner shortly after that, gave me a weird look as I was a hot sweaty mess. She didn’t say anything but I think maybe she knew..

Turns out I also like to dress up like a woman and suck cock.

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