Continuing the story about me and James. Over the next couple weeks we had lots of little encounters kind of hinting or teasing each other about our dicks or sexuality. We talked about when we jerked off with each other and joked about being bigger than the other. We would make jokes about his neighbor’s hot daughter that was a year older than us. A cute tan little blonde 5’2 small framed with little boobs and a nice ass. 

He claimed he got to see her boobs because she was out tanning topless. Me being jealous and half believing him because it seemed unlikely. I joked he liked her cause she had a small chest and looked boyish, insinuating he was gay. 

James would also purposfully make himself hard in his basketball shorts and cup his hands around his dick to outline it in his shorts. Then “trick me” into looking at it and call me gay for looking. Slowly we became more comfortable making sexual references or joking about each other’s sexuality.

One day we had spent the morning out fishing and ended up back at my house to jump in the pool and cool off. On the way back to my house we were talking and I can’t really remember how the conversation went but we ended up talking about the classical question of “how much money would it take for you to suck another guys cock.”

We all know this question and have heard it before. Most of the time guys will quickly say huge numbers like one million or one hundred million. The higher the number the less gay you would seem. Well I decided to be funny and joke around and quote a classic “well twenty bucks is twenty bucks.” 

As I laughed off my joke he quickly jumped and responded with a “Really!?” sounding a bit excited at my affordability. But it also seemed like he sounded a bit questioning with his response. I then kind of awkwardly continued to play it off as a joke, even though in my head I was thinking I’d totally do it for free.

Pulling up to my house, we parked his boat at the dock and decided to race each other to the pool yelling, “Last one in is a rotten egg,” as we pushed and shoved each other grabbing each other shirts to slow the other down. We both pulled our shirts off in the process to not get them wet. We ran to dive in still half wrestling and trying to run at the same time. 

We ended up roughhousing and trying not to drown while arguing who had won the race. Me getting a jab in saying he had won the race just like the last race we had, while grinning and winking at him. Him reacting to my comment proceeded to grab me and start wrestling more. We thrashed about, grabbing at each other, trying to throw one another while the other resisted and tried not to drown. As we wrestled we would of course grab at each other’s shorts to get a grip on something for better leverage. Which led to arms and legs brushing against each other accidentally. 

During all of this I started to get a bit of a hard on from feeling myself brush against him and thinking about the conversation from earlier. Trying to not be obvious about it I tried putting some distance between us and swam away so I could tuck it in my waistband to hide it. Only he grabbed me from behind and picked me up like I was going to get thrown over his head and body slammed. At that moment my butt rubbed against him and I felt his semi hard cock pressing into me as I tried to wiggle out of the bear hug he had me in. I slipped my hand down and brushed against it to make him realize I knew what was jabbing me and also so I could cope a feel and tease him. 

Him realizing I could feel his boner and the shock of my boldness caused him to release me and push me away. I dove away from him under water and turned back to face him. While we were both under water we looked at each other and I “jokingly” did the hand/mouth motion that I was jerking and sucking a cock to tease him. Also to play off the conversation we had earlier. 

He looked back at me wide eyed with excitement and nodded his head in approval while thrusting his hips like he was humping. James then proceeded to pull the front of his shorts down and flash it to me. I got to see all of it for the first time. Though we were under water and I could only see it through my blurred chlorine filled eyes. He was definitely a little bigger than me. 

I’m pretty average only measuring about five and a half inches on a good day, and about five inches around. From what I could see while under water he looked like he was more like six or seven inches and probably thicker than me. 

We locked eyes and he gave it a few tugs and looked down at it and back to me insinuating, “come and get it.” Again I opened my mouth and pretended to suck an imaginary dick to tease him. 

I’m sure if he was closer to me at that moment I would of ended up with his cock in my mouth giving it a quick suck before needing to come up for air. But he was at least ten feet away.

After that we both came up for air and looked at each other. James asked if I wanted to. He said we could go inside and try it. But sadly my sister was home and we were already being loud and risking her catching us in some compromising positions. Also it was starting to get closer to the time my parents would be home from work so I told him that and told him I’d think about it for another day. 

We got out of the pool and talked a bit more as he gathered our stuff up, cleaning up and drying off. Before he left he made sure to remind me he was definitely willing to pay me the 20 bucks and we both kind of smiled and laughed about it.

When I tell you bedtime couldn’t come quick enough. I swear I was rock hard all evening thinking about earlier in the pool. Now that I had actually seen his cock and got to feel it (through his shorts). I couldn’t wait to jerk off later. 

During dinner I scarfed down my food to finish before everyone else and I snuck off into my sister’s room on the other side of the house. I quickly ran to her dresser and since I'd been through it before I knew exactly what I was looking for. I grabbed this little black two piece string bikini with a little white heart on bottoms near the hip. Trying not to disturb too much I closed the drawer and ran back to my room and hid it with my little collection of lost and forgotten stuff from my sister. 

After dinner I went to take a shower and knock the days salt, sweat, and chlorine off from earlier. While in the shower I took a pair of hair trimming scissors and trimmed up my pubic hair, borrowing my sisters razor and shaving around my cock and balls as best I could. 

I’ve never really been a very hairy person, and as a teen I really didn’t have much hair on my body except for my head and privates. Even my leg hair was pretty thin and what little I had was sun bleached and not too noticeable. I couldn't grow  respectable beard until my late twenties. Since my hair wasn't very noticeable I decided to go ahead and shave my legs too. Risking that my parents might notice a little detail like that and ask questions.

After my shower, like usual I excitedly waited for everyone to be asleep and did my routine of grabbing my dad’s laptop and locking myself in my room to lie in bed and watch porn. I grabbed the bikini out of my closet and slipped the bottoms on, marvelling at the feel of my smooth shaved cock on the inside of the bikini bottoms. Turning to the side to admire my girlish ass in the full length mirror hung on my closet door. 

I then put the top on and tied up the strings around my back and neck. They kind of tickled while dangling loose along my back and neck, which made it feel that much more girlish too me.

Being thin I had absolutely no cleavage, so I stuffed a folded up sock on each side to at least give a slight bump to my chest. At least I had a nice round girlish ass and nice legs from playing soccer for the last seven years. 

I stood and stared at myself in the mirror and from the neck down I felt like I could totally pass for a girl. Besides my little cock straining to get out the front of the bikini. Luckily it’s small enough to still kind of tuck away into the front fabric. 

I even tried tucking it back and closing my legs to hold it behind me. This really made me look like a girl from the front. I did a few more poses admiring my ass while bending over and doing other compromising positions before crawling into bed to start my porn adventure. Even the sheets felt different now that my legs were nice and smooth. The feel of the soft fabrics sliding over my smooth body, along with my naked cock sliding around the inside of the bathing suit bottoms was just pure ecstasy.

I searched for some videos of gurls like me in bikinis but back then there wasn’t near as much content out there. I ended up just watching straight porn and pretending to be the girl in the bikini getting taken on the side of the pool deck or flirting with the hot guy in the hot tub rubbing his cock under the bubbles. Teasing him till he sits up on the side and I had a dick staring me in my face. All things I would of loved to be doing while shaved smooth and dressed in this little black bikini.

It didn’t take long for me to cum the first time, I tried not to make a mess and hit the bikini top and tried to catch most of it in my hand before licking and cleaning my hand off pretending it was James cum and his cock that I was cleaning it off of.

Thanks again for reading. In the next part I will go into detail about the next time I see James and my first time fully touching and tasting his cock.