V-Carded! An Twenty-something adult male's struggle with virginity and sexual frustration

A moment over a decade in the making.

Ah right…there IS one other thing that happened that crazy evening…

The Beautiful Kind and I got back to my place about 9PM and raided my liquor selection but unfortunately my fridge was a little empty when it came to things to mix with it. I had a pack of Pop-Ice sitting up on top of my fridge and TBK suggested we make cocktails with that. Definitely an unusual idea but it actually didn’t taste that bad.

We went upstairs, undressed each other and hopped in the shower for some soapy and imaginative fun. After the hot water died - damned my landlord - we toweled each other off and retired to the bedroom. On the bed I pampered her body with my lips and tongue and finally moved my face between her legs, staring straight into her beautiful pussy. After teasing her for a little bit and trying to recall everything I had read in a moment’s notice, I ran my tongue up her slit as she shuddered.

I wasn’t sure what pussy was going to taste like after all the tuna and fish jokes you hear in adolescence but there was really nothing to worry about…no big deal at all. I went very slowly at first and then working on applying pressure to the clit, once in a while asking TBK how something felt or if I was hitting the mark. I got a little worried that I was asking too many questions, but I was trying to learn and was only thinking of her. It’s tough to notice what you’re doing down there when you’ve never done it before, so I was hoping I was hitting the right spots.

I realized that she preferred something faster than the book had suggested so I sped up the pace a bit and prayed my tongue would hold out. At one point I inserted two fingers into her and she went nuts. My ultimate goal was to massage her g-spot: palm up, come hither finger curl, look for spongy area….AH, there it is. I think I needed more practice at working that g-spot as TBK said she didn’t get anything out of it. But I must have been doing everything else right as she spasmed, hollered and yelled that she was having an orgasm.

Down below, my penis was having some of the same problems as last time and wasn’t fully hard yet. I stroked myself as TBK watched and eventually fucked her mouth for extra encouragement. Finally I was hard enough to roll the condom on and I retreated down the bed to get into position. I massaged my cock up and down along her pussy…and then slowly slid it in. And thus…

…my v-card has finally expired. And good fucking riddance.

The sensation and feeling of being inside her was very similar to my first blow job, very different from what I had expected and a new feeling all around. But it was warm, tight and wonderful.

TBK and I tried missionary position at first and I realized that perhaps I need to be hitting the gym a little harder, god damn, sex takes quite some work! Missionary was tricky because I was still a little softer than normal and I slipped out at times. We eventually switched to doggy style and this made things easier as I could pull her back into me on the thrusts. I tried to stop it and hold out for as long as I could, but I couldn’t stop the oncoming ejaculation.

We cuddled for a little bit in the afterglow lingering on the fact that I was no longer a virgin. “SHAME ON YOU TBK…corrupting an innocent virgin just so you can get off,” I scolded as I spanked TBK, who giggled. Then when we were ready to go again, I brought out my little “surprise” that I had brought for TBK for our original date…an ordinary black vibrator. I know, doesn’t sound particularly exciting or original, right? Wrong. The vibrator wasn’t for her…it was for ME.

I turned on the vibrator and applied it to my chin, essentially turning my tongue into a real live vibrating sex toy. (Let’s just say when you’re not getting any that you get quite the inventive imagination to compensate.) I kissed her and teased her breasts with my super-tongue, then went down on her once again as she went nuts. It was VERY tricky holding the vibrator onto my chin, massaging her g-spot (or at least trying) AND focusing my tongue wildly on her clit at the same time. But TBK seemed to highly enjoy it as she tensed up, screamed and exploded again.

She asked if I wanted her to get on top…need you ask? I rolled on another condom and TBK mounted me. Woman on top is a very popular position for men and I absolutely see why…TBK looked and felt absolutely fantastic riding me. This was also a better position for me as a virgin because it took a little less effort on my inexperienced part. We screamed and moaned and I spanked her ass at random times, asking something to the effect of how dirty she felt to be fucking a virgin. Unfortunately once again I couldn’t hold out for too long…

I was a little disappointed that I couldn’t last long enough to properly give her an orgasm from sex, but I thought I shouldn’t be so hard on myself for my first time. Besides, I had given her two orgasms from oral which is a feat for a virgin alone, and I’m sure most disgruntled women with duds in the sack would more than settle for that.

I was wired to go again, but TBK was getting a little tired and wanted to crash. Say what…the virgin conquered the sex goddess? I’m honored We spent the rest of the night cuddling and spooning which was very nice. The only thing that sucked was the fact that I run on far later hours than TBK and didn’t fall asleep for the longest time. I had looked for sleeping pills in the medicine cabinet prior to turning in, but I was all out. Eventually I dozed off and had a very perverted dream involving her and I.

The next morning I felt TBK’s hand on my cock and she started playing with it. This took me by complete surprise and god damn, it was HOT and her touch FELT SO GOOD. I got hard very, very quickly and immediately I could tell that my penis was far more responsive than the previous night. She asked if I wanted to go again and she helped me put on the condom.

We had Sunday morning sex in spooning position which was quite nice. I began to noticed that TBK responded to deeper thrusting than I was giving her, so I continued to do my best but the spooning position wasn’t the greatest for that kind of rough sex. We switched to doggy style and I penetrated her as deep as I could on every fourth thrust or so. Perhaps it was the condom I was using, but my performance felt better and I was lasting a little longer this time. TBK finally screamed that she was about to cum, and to the moment she said that I felt my own ejaculation forthcoming. We both damn near woke up the neighbors in an incredible moment - we came together.

We dozed off in each other’s arms again for a bit, then eventually stirred around again. I asked her if she wanted to get off one more time before she went (I had oral in mind) but she said something to the effect of being satisfied so we didn’t go any further from there. We got dressed and chatted on the way back to her place about our evening together and that concluded our date.

Posted September 17th, 2008 in Sex

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