I never got into Manda’s little pussy, (hat’s off to whoever got that little hot fucking cherry) but Manda was the first girl that ever saw my dick and that I ever saw naked in the flesh.

Manda’s brother Jerry and I were friends. Years earlier at the hands of another friend I had discovered how using Dungeons & Dragons I could get other kids to role play with me and do sexy stuff. My friends and I had traded blow jobs and it even progressed to anal, but that was before any of us had even really reached puberty. I was probably the first to reach it starting in about the 5th grade and enjoyed the company of Jerry and a few other friends throughout Junior High. One hot, humid, Southeast Texas summer day in 1996, Jerry and I decided to play our version of D&D and fool around. We went out to his barn and climbed up in a little loft area that was out of sight to prying adult eyes. Unfortunately, we couldn’t shake Manda. I looked at Jerry and just kind of smiled. We didn’t need words, he knew I was thinking about my first pussy. We explained the rules to Manda and how the game might go, and she seemed game enough and wanted to play.

The first couple of encounters in the game involved Jerry and I losing articles of clothing. We worked up to a kiss between us before we made sure Mandi was damaged by a young black dragon and had to lose her shirt. She had no breasts to speak of and was more than happy to lose her shirt due to the heat. We progressed until Jerry had to suck my cock. I pulled my undies down and my erection stood our from my body, my black pubes clinging to the base of my cock. Jerry was a great cocksucker and got to work. I didn’t let him bring me off and I think Manda found that slightly disappointing. She was watching with rapt attention the whole time. The next turn I ended up blowing Jerry. Jerry had only the feintest blonde pubes near his cock. I recall his nectar was always quite sweet and that day was no exception. I sucked him to orgasm, held it in my mouth, and showed it to Manda. Manda just said “Ewww” but never looked away even a little.

Finally, in the course of the game Manda “died”. The way we played, the only way to get back alive was to do a sex act. Manda didn’t want to do anything with her brother, she said that was “gross”. Jerry just grinned at me. So we tried to get Manda to suck me. She took a lick of my cock tentatively and started to put the head in her mouth. She put her head down and gagged herself shooting up for air and saying that she just couldn’t suck my cock. I was thinking damn it, girl! I needed release by that point. I asked her about her pussy and she didn’t feel comfortable having vaginal sex, but she was open to anal. So, I flipped her around over a little table that was in the loft. Jerry and I had been at this for some time and so we made certain we had vasoline. I dipped my fingers into our stolen vasoline and started working a finger, then two into Manda. She moaned and moaned saying things like, “Oh it feels so strange, so good.” And “Oh it tingles, it tingles.” Finally, I decided she was ready. I lined my hard on up to her pucker and I pushed slowly.

Manda yelped loudly. I shushed her because Iwas worried about someone hearing us and catching us in a rather compromising position. She quited down and I kept applying pressure. Little by little my cock entered her little asshole. I pressed and pressed until my balls were touching her pussy. I waited a moment letting her adjust, then I started to stroke. I had been doing anal for a while by that point, so I could normally hold out a good bit, but with a new partner and, moreover, one who wasn’t male, I was in a fog of hotness. Manda was loving it. She was moaning, breathing hard, and rubbing her little clit. It didn’t take long before I was emptying the contents of my balls into Manda’s hot ass. As I was doing so, she hit an orgasm and yelped again. Her brother jumped up on the table and put his had over her mouth so she wouldn’t cry out so much.

I withdrew my dick slowly. As I did, some of my boycream dribbled out and down the crack of her ass and over her pussy. She hadn’t wanted to give the pussy up, but I’d still like to think my semen was the first that made its way into her. I wanted to fuck her pussy so bad, but all I ever eventually got was a little outercourse from her before she got a boyfriend and didn’t want to play with me and her brother anymore.

Part 2: Jess

Jess and I started dating the Summer after my Freshman year of High School. I most certainly wanted to get laid, but I was very nervous about doing anything physical with Jess. She is still a family friend and most certainly still was back then. Her family still lives across the street from my relatives and our families still get together sometimes. I’m sure they thought for sure we’d marry, but it just was not meant to be.

Jess surprised me by wanting to get physical almost right away. I was afraid to hold her hand, she grabbed mine. Even her Dad seemed to encourage us to be a little closer than I was ready for. One time we were watching a movie on the couch. I was sitting with some space between Jess and I and he came by and pushed me over onto her shoulder. I guess the old man wanted me to have more game that I was having. It was confusing though, since Jess’s parents were somewhat religious. That was month 1.

In private, Jess was even a little more forthcoming. Month 2, she kissed me first and then grabbed my hand and put it on her ample teenage breast. This progressed eventually to making out. By month 3 she upped the ante and started grinding my cock through my jeans when we would make out. I was always embarrassed leaving her house while trying to make sure her parents didn’t see the cum spot on my shorts or jeans! Month 4 she started taking our shirts off when we would make out and having me play with her breasts and suck on them. Month 5 the pants came off and we were grinding in our underwear.

By this point, I couldn’t take anymore. I wanted her pussy. In Month 6 we progressed to oral, but it just wasn’t enough for me. This is where things took a slight turn. We were both completely horny for each other, but we couldn’t find the right place to have sex the first time. I got her out alone in my Mom’s mini-van (I was 16 and driving by then) but she wouldn’t let me fuck her in the mini-van and instead gave me a hot ass blow job. (The mini-van would eventually be the site of one of our most memorable nights together. I still recall that one when things aren’t going great in my marriage, but that is one for another time.) We hit several parties that October together but the timing was never right. I was beginning to get frustrated with the situation.

By this point, I was living across the street from her. My Step-Father and I were fighting and so my relatives took me in. This gave us more chances, but there were lots more watchful eyes and less reason to be tooling around in the car. Finally, it happened that her parents were both at some function for her sister and didn’t make Jess attend and my relatives were at work until at least 6pm. Things were shaping up nicely. I took Jess to my room and I undressed her as quickly as possible. I still remember she was wearing white panties with a pink fringe and blue flowers on them. I removed them and looked at her perfect little pussy. Just the right amount of chestnut brown hair around it. Gorgeous by any standard. I undressed and we made out for about 20 minutes. When I couldn’t stand it anymore, I rolled over on top of her and rubbed my bare dick against her bare pussy. I did this for a bit as she moaned and cursed under her breath with the pleasure. I lined myself up to enter when she asked me, “Do you have a condom?”

Fuck me I thought. I reached over to my bedside table and got one out. I ripped open the package and fumbled with the thing. I had never used one and had only briefly been schooled in the idea. I tried to roll it over my dick but it was really tight and I couldn’t get it comfortable. Meanwhile, Jess was rubbing her little clit furiously. I told her I was having trouble with the condom. I told her we’d probably be alright since it was our first time. Being stupid teenagers, we probably actually believed that bullshit. She said fine, lets do this.

I lined myself up against I rubbed my dick in her juices and stroked over her clit a couple of times. Then I lined myself up with her vagina. Her pussy. That honey hole. That place I had longed to be since I first learned what sex was at 10. In my lack of knowledge or experience with pussy and my excitement, I just kind of jammed myself in. Jess’s eyes bugged out and she said “OH” very loud. I stopped worrying that I hurt her. I definitely had, but it was only temporary. I was sure to burst soon I just knew because of the new sensations and the hotness. Her pussy was hot and wet around my dick. There is just nothing like pussy to be honest. I was an opportunist and I had plenty of ass before from boys and a couple of girls, but pussy was a new high. Electricity coursed through my dick and all throughout my body. I’m sure sex has felt as good since, but I really couldn’t tell you when. I thrust myself into her for about 3 or 4 minutes tops and then unloaded a torrent of cum I don’t think I’ve ever unleased since. My cock shot and shot for a solid 30 seconds. When I pulled back I saw my boy-cream fall out of her and run down the crack of her pussy over her ass. It was fucking hot.

I grabbed my boxers and cleaned up the mess. This would be the first of many times. Jess got on birth control not long after that because, once you’ve had the real thing, going to condoms in kind of a drag. I still regret the way that I broke it off. Jess isn’t near as hot as she was back in High School, but I could easily fuck her every day and get off every time in her middle age just because of the hotness of the memory. She is definitely one of my favorite masturbatory memories.