Tales from my Teens: Stolen Virginity

As with any adolescent male with a social life plagued by the blight of having a penis that became erect at even the slightest change of the wind, I was a virgin and I couldn’t wait to get laid. After discovering that more than just urine was able to escape my urethra once given the right motivation, I had picked up “Challenge Masturbation” as my hobby. With the level of dedication I brought to it though, it could have easily been mistaken for my career choice. *writes “Challenge Masturbator” down on his resume*

I used to masturbate (using the term here to count ejaculations) two and five times per day; most times in one attempted sitting. I say “attempted” because at that age, ejaculating even three times in quick succession would make your testicles hurt or cause you to pass out. At one point, I was probably a connoisseur on masturbating until one passes out because it became fun to me and was the aspirations of my masturbation sessions. Don’t judge me; it has aided my sex game in the long run.

Eventually, all guys addicted to masturbation will get to a point where the novelty of it will wear off. When they get there they make the transition to developing a mack game and trying to score chicks. I felt confident and prepared for all of this when making that switch. I had countless hours under my belt for macking on chicks in MSN chatrooms and trying to get them to take their tops off. Then there were also the even more countless hours of porn that I had been watching over the years that taught me EVERYTHING I needed to know about sex (apart from listening to the older guys talk).

"WTF JUST HAPPENED???!!!"

“Find a chick, tell her what she wants to hear, get to put your penis in her, wiggle around a bit and smack her butt, then finally cum all over her face and watch her lick it”. That’s all there was to sex to me. Well, that and the advice of my homie Daree to not “fly ya fus water and breed da gyal” (get the chick pregnant the first time I had sex), so condom usage was a “must”.

Armed with the scholastic knowledge of an 80’s porn star, I went in search of my first “sugar bowl”. I did indeed find her, and she came in the form of a female a few years older than I was. I thought this was kind of cool not to mention the kind of bragging I’d be able to do with losing my virginity to an older chick. Little did I know that I was setting myself up to literally be raped of my innocence in what would end up being probably my worst sexual experience ever.

The chick

She wasn’t exactly the prettiest creature person in the barnyard on the market but she had a vagina and that’s all that mattered (at that point). OK, maybe I’m underselling her looks a bit (blame the weave) but if it was one thing I’d give her it’s that she probably had the most amazing body I ever placed my hands on even to this day. I knew her through a friend of a friend and only spoke to her “on and off” on MSN when I guess one of us was bored.

I honestly didn’t see her as a candidate for some poontang because as I mentioned before she was older than I was and chicks always went for guys older than them. Despite being greatly sexually attracted to her, given that previous fact I didn’t see the point in wasting time and mack on her. She was just “one of them other bitches”.

One night we were talking and she ended up babbling about how many guys were hounding her (something she took great pride in and always spoke about *rolls eyes*). She probably picked up on how much I wasn’t enthused about talking to her, and she said the magic words for any thirsty dude on the computer late at night: “I feel so horny right now. I haven’t had sex in forever.” Automatically, the two other chicks I was listening intently to about how their days went didn’t exist anymore.

Without getting into too much details, the convo went down the road of her telling me why she was sexually deprived, how much she was alarmingly addicted to sex, and us exchanging stories of our sexual exploits. What? You didn’t expect me to be all “virginal” and not have a commanding role in the conversation or at least have something equally intriguing to contribute to it right? I lied through my teeth about so much $h!t that it wasn’t even funny. I was basically telling her storylines of porn I had seen and the best part was that she was eating it all up.

All our conversations after that were always sexual in nature. This chick ended up telling me some of the most messed up things that she had done which still causes me to gawk in disbelief. This was good that she had become that comfortable with me, but talking to a chick about sex and actually having sex with her are two different things. I needed to perform that “friends to fuckers” conversion. This then started my plan to always be the instigator of her horniness.

This chick would get so worked up over our conversations and with very minimal input from me. All I needed to do was get her started, and it pretty much took care of itself. Secretly, she was slowly becoming my sexual goddess and this started my ever increasing lustful desires to have sex with her; but I had to be cool about it. The last thing I wanted to be was one of those guys she was always clowning behind their backs.

The way I saw it was that the best plan of action was to get this chick so horny that one of two things would happen. The first being she’d end up having sex with me since I was (hopefully) the main cause of her being horny. Either that or she’d end up having sex with some other dude in which case I’d hope her vagina falls off and into a pit of lava rendering it useless to her or anyone else thereafter. *insert Mojo Jojo laugh here*

You’re invited!

Skipping past two weeks, this chick invites me over for a movie night with a bunch of peeps. I got there fashionably late only to realize I was actually quite early. Well actually no; a whole bunch of the people who were supposed to be there bailed at the last minute (as was explained to me).

I made myself at home, started pigging out on the snacks and stuff she had spread out on the dining room table, then headed for the living room. I realized I had probably left my phone back on the table shortly after so I went back into the dining room to retrieve it. On getting there, she was just coming off what appeared to be a somewhat disheartening phone call. I asked her if everything was fine and she notified me that the last two people we were waiting on weren’t going to be able to make it and that it was just us.

I shrugged and “ho-hummed” my way back into the living room and then she called me. “FUCK!” I thought, “Wasn’t I just in there? Why the hell would this bitch wait until I was about to sit down again to want me for some shit?” I grumbled and made my way back to the living room where she was still standing where I left her.

“What’s up?” I asked.
“Nothing really, I’m just kind of upset that tonight didn’t work out as planned.” She replied.
“That’s cool, we can still watch some movies and have a cool time; no worries.”
“Hmm, true… but are you sure you want to do that?”
“Yeah, I’ve got no problem with that. I mean I made it all the way out here already anyways so it doesn’t matter if it’s just us.”
*she steps closer and looks at me weirdly*
“Exactly! So that’s why I’m asking you if you’re sure you want to watch movies.”
*gives her quizzical look*
“Umm yes. Why wouldn’t I wa-”
“-JUST watch movies?”
*she moves “breathing on me” close*
“I err… ahh…”
*she grabs my crotch*
“…oh!”

The naïve virgin in me was now in control. I honestly didn’t come there with any intentions of there being sexual contact between us so I was not mentally prepared. I was just supposed to go there, hang out with a few peeps, watch movies, and leave. I felt like a scared kitten and any excuse I could come up with to get myself out of that situation I would have used it.

Just as I was about to run out of the house screaming like a little girl, my ego popped out of nowhere and reminded me that I had been running my mouth off to this girl for the past few weeks and I had to “represent”. After that little “be a man” pep talk from my ego, I turned to him and asked him what to do next. He then looked at me and responded, “You’re on your own there homie. I’m just here to make sure your dick gets hard and you don’t bitch out. You shouldn’t have been talking all that shit!”, and then he disappeared.

I always found it funny how the male ego gets you into situations and then just leaves you hanging when $h!t is about to go down…

Schlong in hand, she led me through a hallway cheerily pointing out the doors for the various rooms. While she was there leading me along skipping and clipping her heels, I was sweating buckets and freaking the hell out. I think my biggest fear was being found out to be a phony and having to deal with her laughing at me for being a virgin.

I could see it all already. I’d wake up the next day and there’d be a billboard on Independence Drive with my face on it and the headline “Pretentious Virgin”. I’d buy a newspaper and the center page spread would be me and the headline “30 Seconds Max”. Everyone would be laughing at me everywhere I went and wearing white ribbons to pay respects to the tragedy that was my sex life. Flags and bumper stickers would be printed and distributed throughout the island and just as I was the Prime Minister was about to declare it a national holiday, I was snapped back to reality by her telling me that we were now in her parents’ room.

It wasn’t so much of the fact that she was telling me that this was her parents’ room that caused me start thinking logically again. It was the fact that I finally realized that this b!t(h was giving me a guided tour of her house… with my d!(k in her hand. Like who the phuq does that?

As I started to think about how weird this chick was for doing this, my confidence started to grow and I felt more comfortable trying to commandeer the situation. Both of my “heads” mentally became one and formed an Ultra Megazord of cockiness that sent a thundering rush of blood to my penis and made it even harder. She definitely noticed this and stopped mid sentence and gave me this surprised smile.

My confidence was now probably at its peak. I realized that all I needed to do was be as sure of myself as those guys in the pornos and I would be home free. I mean, porn and acting like I had all the experience in the world from watching it was what got me here in the first place, so that was what was going to get me through it. I was going to tear that pu$$y up!

Feeling even more full of myself I grabbed her wrist, turned her completely around to face me and asked, “Bitch, we fucking or not?”

Yeeeeaaaah… that’s probably what I was thinking at the time but that certainly wasn’t what came out. Actually, I didn’t even get to say anything at all. The second I spun her around, she grabbed my shirt and pushed me backwards; causing me to lose my balance and falling to my doom… into an Ab Lounge? What the phuq?

I don’t know where the damn thing came from but it saved my life… momentarily. Before I even got the chance to thank God for putting the Ab Lounge there, she had already hopped on top of me, taken my shirt off, and was grinding her cooch furiously against me. I’m sure it probably felt good to her because she was rocking the nuts and bolts out of that Ab Lounge. However, despite helping me achieve a good abdominal workout, each one of her thrusts felt like it was going to cause my d!(k to bend to the point where it would break.

Like I said, she had an AMAZING body and the strong legs of a horse so getting her off me from that position wasn’t exactly the easiest of things. Thankfully she eventually got tired of that and got up. Feeling defeated, I somehow managed to stumble my way out of the Ab Lounge. I thanked the Lord that the worst was over and glanced around the room for my mislaid shirt so I could leave.

My eyes then found a pair of panties and some booty shorts that her mother probably left laying around. Then I saw a shirt that looked familiar a few feet away on the ground. Just as I was piecing things together, a bra fell right next to the shirt and my eyes started to climb the most perfectly sculpted pair of legs ever gazed upon.

The moonlight was coming through the window behind her and was casting a picturesque halo around her flawlessly proportioned body. I knew she had a banging body (did I mention that before?) but I never imagined it would have looked this good naked. She looked like one of those video hoes from a rap video. Just everything on point and-… OK, Imma stop sucking her d!(k now… (no homo)

The pain in my penis vanished as my Ultra Megazord pumped another gush of blood through it. My body slowly gravitated towards hers while enigmatically relieving itself of the last bit of clothing on it (I seriously don’t remember how my clothes came off). I grabbed her firmly and laid her on the bed like a valiant knight who had just saved his princess from a fire breathing dragon.

I was in control of things again. Gone was the screaming banshee that almost bent my d!(k into a pretzel on the Ab Lounge and present was a more docile and submissive sex slave. “Ego” kicked in and I was in my cocky porn star mode again.

As I prepared to mount her, my homie Daree’s words to not “breed um” crashed into my ear drums. I put a pause on the proceedings to get a condom out of my wallet. Stepping back towards the bed, I used my teeth to tear open the wrapper and well… I think that was where things started to go downhill.

The unknown

I could be wrong, but I think something about the visual of me opening that condom wrapper like I was snapping into a Slim Jim caused her brain to short circuit. Before I went “Randy Savage” on the wrapper, I am certain we were about to “make love”. You know, with all the feelings and gay emotional $h!t that all chicks are programmed to think losing their virginity is all about. However, her seeing me open the wrapper caused her to stop thinking “he’s gonna make love to me” and switch to “oh he’s going to rip this pussy to shreds”. Now enters the Mrs. Hyde that I met earlier in the Ab Lounge…

I watched my confidence run off into the distance as she snatched the condom out of my hand, put it on, and pulled me on to her. My knees became jelly and I looked down at my d!(k for advice on what to do next since my confidence had abandoned me. “NIGGA FUCK HIM!!!” he responded, “The pussy is right there; the fuck we need him for? I GOT THIS!!!”

I looked back at her and there was this “what’s the holdup?” look on her face. I grabbed my d!(k and attempted inserting it into her cooch. That didn’t work out too well since my coordination was completely thrown off by my d!(k and I holding hands and spinning in circles singing the “I’m About To Get Laid” song. After maybe 20 seconds of bumping into her thighs and pretty much everything else BUT her vaginal walls, she grabbed my d!(k and put the tip of it by this little indentation between her legs.

A gut feeling hit me and told me to push a little and as I did that the indentation got a bit bigger. “Hello, what is this we have here?” I thought. The tip of my d!(k got a bit warmer as I pushed a little more and then it dawned on me. “I’m getting some pussy ya’ll!!!”

I paused there at the entrance and was planning out with my d!(k who we were going to call first and the epic story we were going to tell about it. The words, “OMG, I’m up in some poontang!” were bouncing around in my head and I actually forgot about the chick for a minute. She however didn’t forget about me since she wrapped her legs around my lower back and pulled me towards her. The sudden presence of warmth which engulfed my penis after her doing that was something neither my d!(k or I were prepared for. That lack of preparation became alarmingly evident to me because that one “guided” thrust was all it took for me to cum… FAWK!!!

“Is it over yet?”

I looked down at my d!(k and screamed, “DUDE WHAT THE FUCK?! I THOUGHT YOU SAID YOU HAD THIS!!” He looked back up at me puzzled and exclaimed, “I did bro; I don’t know what happened. My bad?” The exchange between us continued for a few more seconds and then we both realized something; we were still having sex.

There were two things at work here. Apparently, all those years of challenge masturbating had paid off and my penis was now “trained” to stay erect even after ejaculating so I was still “good”. The second thing happening was that this chick was horny as phuq and she (with her legs tightly wrapped around me) was still forcefully thrusting my body towards hers.

This was a good thing because she wouldn’t have to find out I was a “half-second” punk. Added to that, that nut I had just busted was one of those that drains your balls COMPLETELY (the guys know what I’m talking about) so I had no energy at all left to have sex with her. I was honestly quite content with just laying there and having her strong legs toss me around like a rag doll. That was only until I realized she was just warming up.

Two minutes in she started grunting at me, “Harder! Deeper! Faster!” I thought to myself, “Bitch you’re the one fucking me. I’m honestly only here now as a requisite for sex.” I didn’t do anything more (not like I could anyway) and she took it upon herself to change this by violently pulling me against her. I probably wouldn’t have minded it much if it wasn’t for the fact that her heels were “biting” into my lower back and was creating a sore spot. Additionally, her hip bone wasn’t exactly covered in a layer of cushion so that was another issue manifesting itself.

This wasn’t the slightest bit enjoyable and I wanted it to end. What made things worse was that the pain was becoming even more unbearable. With the energy I had left, I tried pushing myself off of her but that only caused her to tighten her grip on me which translated to more pain. She then gave a grunt that sounded like the Boogey Man asking, “Where the fuck are you going little boy?” and then continued having her way with me. I was about to scream out and beg her to stop but my ego popped up again and told me to stop “being a little bitch”. Then I was once again reminded about all the $h!t I spoke to this chick and how much “rep” I had riding on this.

I bit my lips, bore the pain, and regretted letting my ego get me into this mess. In all the porn I had seen, the guy had always made the chick his b!t(h and now this chick was having her way with me. This wasn’t the valiant story of great conquest I had envisioned it being. Instead this was a tragic emasculation. Every ounce of masculinity I had was now curled up into a ball and crying on the inside. I wanted my mommy.

Eventually her grip on me started to loosen a bit and her thrusting motions were now a lot slower. I celebrated as I realized that the end was near. I timed her weakening thrusts and successfully pushed myself out of her grip.

I rolled over on to my back and let out a sigh of relief. My thoughts now were to get my clothes on and get out of there as fast as possible. As I prepared to get up and make my escape, I felt an unusual weight on my chest. I opened my eyes to see that she had mounted me and was about to have her way with me again.

Distraught, I geared myself to kick her off me and just run but then I thought, “Hey, this feels kinda good.” She was actually taking her time now and not trying to use her cooch to snap my d!(k off like a dry twig. No sooner had I thought this, she increased her pace I started having flashbacks of the Ab Lounge again.

What made this episode a bit different was that she added the extra effect of loud moaning. Here I was banging this chick that looked good enough to be a video hoe and she was moaning like an experienced plumber was laying “the pipe”. Can you say, “ego boost”?

I ignored the feeling of my d!(k being ripped off and forced myself to enjoy this. My enjoyment was short lived however as she leaned forward and braced herself by digging her fingernails into my sides. The pain caused by this was too much for me to keep in so I had to let out a girlish squeal war cry.

What a time it was to find out that guys making noise during sex turned her on. When I let out my war cry, her moans got louder, she rode me harder, and dug her hands into me even more. That only caused me to let out an even louder war cry and well… I bet you can pick up on the vicious cycle by now.

When things got to the point where she was using her fingernail to take bone samples from my ribs, I had no voice left and she was now on top of me suffering from self induced rigor mortis.  The last thing I remembered was her taking a really deep and long breath, then she just held it and stopped moving. I honestly didn’t mind her dying on top of me or anything since that’s the type of stuff movie and book deals are made out of. My issue was that she chose to do that while having her fingers stuck into me and I wouldn’t have been able to get them out without going through the world of pain.

Suddenly, all her muscles relaxed as she exhaled loudly and collapsed onto my chest breathing heavily. Despite my ego trying to high-five me on “wearing that pussy out”, there was a little voice at the back of my mind trying to alert me that something was terribly wrong. I couldn’t hear what it was saying over her loud panting so I figured I just had to wait until she was cool again. Moments later, she finally started to get off of me and my hand slid off of her and on to an unusually warm spot on the bed.

Alarmed, I started running my hands over the surrounding area and it felt the same. I felt the bed sheets near to my head and they felt normal, then when I touched the bed sheets by hip area and it felt weird again. It took me a while to start to clue in that this weird feeling was wetness, but where did that “water” come from? The logical answer of “sweat” then came to me.

When she fully got off of me, I realized that my crotch area was wet; unusually wet. Then I also realized that her crotch area was dripping wet; unusually dripping wet. As I switched glances rapidly between both our crotch areas trying to make sense of the whole ordeal, the little voice I heard at the back of my mind was now at the front and his message cleared everything up. This b!t(h had just phuq-ing peed on me.

“…but wait; there’s more…”

The whole of the alleged R.Kelly “piss on you” sex tapes played through my mind. Was it now cool for people to piss on each other during sex? If so, was it so cool now that chicks could be doing it to dudes? I wasn’t down for that $h!t at all but my ego kept telling me, “Just let it slide homie. This is not the chick you want to seem like a punk bitch too. Just leave the pissing part out when you’re retelling the story. You’ll be fine.”

I reluctantly listened and even more reluctantly allowed her to mount me again in a reverse cowgirl. I was fed up with sex. I didn’t want any part of it again and was just about ready to go home and burn all of my porn for lying to me. Just as she was sitting on me again, I remarked to myself about the relative ease with which I was now able to enter her vagina. It almost felt like I could just “slip right in”. I didn’t even thi- “FWAAAAAAAAARRRRRRRRRPPPPPP!!!!!”

What the fu- “FWAAAP!!! ……FWAP!!! ……FWRUP!!!”

My brain couldn’t believe what had just happened. It therefore felt that death was a better option than having to deal with that reality. Every other part of my body was welcoming death with open arms; but my heart just absolutely refused to “give out”. I had seen, heard of, and been through my fair share of messed up situations in life and all of that left me with a positive message and helped me become a stronger person. Try as I may, I couldn’t bring myself to find the positive side of a chick farting on my d!(k during sex. Then to make matters worse, she was looking back at me giggling and continuing like nothing even happened… “FWAAP!!! …FWAP!!! … FWRUP!!!”

The end?

Well no… After literally tossing her off me in a disgusted rage, I gathered my clothes together and prepared to leave. She laid motionless on the bed looking at me startled but I couldn’t bring myself to give a phuq about what she was thinking. I went into her parent’s bathroom and washed my crotch area for about five minutes and left without saying a word.

As I exited the house, that little voice in the back of my mind from earlier was back again, and with a new message. I cringed as I listened to what it had to say then went back into the house. When I got to the bedroom, she was still laying on the bed in the exact position I left her in. “I think I forgot something.” I said. She opened her mouth to respond but was instantly quieted by me sticking my index and middle fingers into her vagina.

I “fished” them around for a little before a foreign (but familiar feeling) object became entangled with one of my fingers. I looked at her as I slowly reeled it out, and observed her twisting her nipples and biting her lips. I was greatly annoyed by her actions, but I had a bigger issue to deal with.

When my fingers had safely exited her grotto, she paused, gave me a repulsed frown and asked, “What the fuck is that?”
“It’s a condom… with no sperm in it.” I replied.
“Wait, you came?” she scoffed.
“Yeah… but umm are you on ‘the pill’ or anything?”
“Ha ha ha, of course not. I want to have lots of healthy babies some day you know.”
“…………………………………………………..FUCK!”

*uploading posts with pics from my phone is a motherfu-… I’ll drop them in when I get home. In any case who needs pictures anyways?*