Pleasuring a Friend pt. 1

Something came over me that night and I couldn’t stop myself.

I discovered an interest in sex at a very young age. I knew I was bisexual by the age of 10. I liked boys just as much as I liked girls. As a kid I would spy on my parents having sex. I would snoop through my parents dresser drawers and see what I could see. Sometimes it was a dildo I found or a box of condoms, typical things you’d find. Sometimes I’d look through my moms underwear drawer. I found at an early age I also liked wearing women’s clothes as well.

There was a girl in my neighborhood that was a year older than I was, Crystal, and she would frequently make out with me and the other boys in the neighborhood while we played hide and seek or whatever we were playing on any given Friday night.

I thought that meant girls liked me but as I got into high school I realized girls weren’t all that into me. Sure there were a few girls that talked to me but I lacked the courage to ask them out and thus, spent my weekends alone.

There was a kid that lived next door to me that was a year younger than me, Joe. He was kind of lame but because of geographic reasons, I found myself hanging out with him regularly.

One day after school when I was 16, Joe and I were just hanging out in my room and I decided, with no intentions or plans, to just put on some porn. Joe and I watched the entire scene and did nothing. I did notice him adjusting himself as I’m sure he noticed me doing the same to my boner. After Joe went home that night, I masturbated and found myself thinking of Joe and wondering what his cock looked like.

I invited him over again the next day and everyday after that until I had the courage to try something with him. Finally I got the nerve to have the “I’ll show you mine if you show me yours” talk. It worked. We were watching porn and I pulled my pants down and kicked them off. Joe laughed a bit as he stared at my 8” cock standing straight up. I covered up feeling a bit embarrassed and told him to take off his pants as well. When he did I was confused as to why he laughed at mine. His was barely 5”. He explained that he thought mine was huge and took him by surprise.

We ended up laying next to each other jacking ourselves off and cumming all over our stomachs. Over the next two years we would get together regularly and and fool around. The furthest we ever went though was getting completely naked and humping each other with no penetration. We’d just rub against each other and cum all over each other’s stomach.

I would regularly suggest that we try oral sex together but he always shot me down. One time I got him to try it but the most he did was lick my shaft once and then he freaked out and that was that.

After high school my mom got a new job and we moved away. Not far, about a half hour south. By now I was 20 and I had just had my heart destroyed by a girl I was dating for nearly 2 years. The kind of girl I thought I was going to marry. In my wallowing and feeling sorry for myself I decided one day to call Joe and see what he was doing. It took a matter of 5 minutes before the conversation took a turn towards the “old days” as Joe referred to them. The old days being the days him and I would fool around. He had mentioned during the conversation that he had been secretly dating a guy for a few months but they recently broke up as well.

Ideas began to stir in my head and I asked Joe if he wanted to hang out. He agreed excitedly but he wasn’t free until the following weekend.

Over the course of the next 10-12 days we talked on the phone a few times and texted a couple times a day. I had made the decision to not jackoff at all over the two weeks so that when I finally got together with him, I had a huge load built up. However, over the course of the 10 plus days I watched a ton of gay porn and found myself more and more thinking about doing stuff I had never done before. I got hornier and hornier with each passing moment. I managed to not blow it though.

It was the day before Joe and I were going to hang out and I had no plans as to what we were going to do. Something in my mind that morning when I woke up told me to just go as far as I could. Do something I had never done or tried before. I got it!

“I’ve got a surprise for you tomorrow night.” I sent Joe a text

I had the house to myself that day and decided to go into the bathroom and do some manscaping. I shaved my face, then my legs, and then my chest and stomach. I trimmed up my pubes as well. That alone took forever lol. Rubbing my smooth body turned me on incredibly! After I was done I went into my moms room and started snooping through her drawers. It had been a while since I did anything like this and even though my mom was in her early 50’s, she was still dating from time to time and still had a nice enough body that she had lingerie and sexy underwear and clothes. I wanted to wear some of her clothes but they were a bit too small. Her lingerie and underwear were a bit more stretchy and I could fit into them.

I found a silky purple spaghetti strap nightgown that I had never seen before. So I pulled it out and tried it on. I stood in front of the mirror and loved it! I found a pair of black satin panties and matching black silk stockings, put them in a small bag and threw them in my closet. I wanted to try makeup as well but if I can be honest, I know absolutely nothing about applying makeup. I tried anyways. I put on some lipstick and eyeliner. Looked well enough but when I put on some mascara, I looked like a $2 whore posing as a clown.

Later that night I was digging thru an old tote that had some stuff in it and after about 45 minutes of looking, I found what I was looking for. An old black witch wig my mom wore a few years earlier at Halloween. As I put it in though, it was much too long. I trimmed it down to a more normal length. It didn’t look great as I was also not a barber.

The next night I got a text from Joe saying he was on his way over. I let my mom know he was coming and I jumped in the shower. I reshaved my entire body which only took a few minutes this time, just for maximum smoothness. As I got out of the shower and dried off, I saw some body lotion my mom had. It was lavender scent and I remember thinking every time my mom wore it thinking to myself “I wish I had a woman that smelled like that.”

As I exited the bathroom I heard my mom’s voice. By the time I got to the bottom of the stairs I heard Joe’s as well. We made small talk with my mom for about 5 minutes or so and then went upstairs to my room.

As I closed the door and locked it behind me I heard Joe’s voice.

“Is that you that smells so good?” He asked

“Mmhmm.” I said as I approached him with a smile

I wrapped my arms around his waist and squeezed his ass. Joe got slightly uncomfortable and squirmed a bit.

“Relax. I’m going to take special care of you tonight.” I said

I leaned in and kissed him on the lips. Just a peck. He pulled away a bit and I reiterated my point of relaxing to him. Joe nodded his head in agreement. I leaned in and kissed him again. This time Joe kissed back. After a few awkward pecks, I gave him a slightly open mouth softer kiss. Joe was still very tense but I could now feel his erection pushing through his pants into my leg. This time I opened my mouth a bit more and pushed my tongue into his mouth and began to swirl it around his. I also reached down and began rubbing his erection. Immediately Joe’s shoulders dropped and he relaxed and started kissing back. He had put his hand on the back of my head and now he was suddenly in control and kissing me.

The feeling of him taking charge, even if it was just a French kiss was such a turn on considering what I had planned.

“You smell so good.” Joe whispered as he came up for breath “..you smell like a girl.”

“I’m your girl tonight!” I whispered back

Joe the put his tongue back in my mouth but not for long as his lips made their way down my neck and my earlobe.

“Oh my god I’m so horny!” Joe whispered once again

I began to unbutton his pants and reach inside. I pulled out his 5” cock and began stroking it. Joe’s arms fell to his side and his head tipped back as he let out a quiet moan. I pushed him towards the bed and told him to sit down. Grabbed his pants and yanked them down to his ankles and pulled them off. Without hesitation I grabbed ahold of his shaft and put his cock in my mouth.

“Oh shit!” Joe moaned much louder

I swirled my tongue around his top and then swallowed his cock whole. Joe let out a relaxing yelp and laid back on the bed. My head began to bob up and down swirling my tongue around his cock. It tasted pretty damn good! Within 15-20 bobs..

“Oh I’m gonna cum!” Joe blurted out

“Mmhmmm” I replied without stopping.

Before I even finished replying, I felt a huge spurt of cum hit the back of my throat. Then a second, third, and a fourth! I took his cock out of my mouth so I could properly swallow and a fifth spurt hit my chin. I quickly opened my mouth and let him drain his balls onto my eager tongue. I have a quick swallow and licked the last drop trickling from his dick and got up and laid next to him.

“Wow!” Joe gasped out of breath

“I’ve got bigger plans for this guy so stay awake!” I said as I reached down and grabbed his now limp dick.

My plans had definitely been altered for the time being but I would eventually get what I wanted out of this night…

To be continued…

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