My First Time

Losing My Vaginal Virginity

It wasn’t until I was a freshman in college. There were a lot of factors at work. I was discerning to the point of persnickety-picky. I considered myself a freak because I fantasized about getting spanked as a necessary preliminary before sex, and was sure that I’d never find a lover to fulfill this desire. By eighteen years of life, I was set in my ways; I masturbated a lot and always used self-spanking for foreplay. My virginity felt like a burden that I’d carry forever. In school and social situations, I felt like I wore a large scarlet letter V emblazoned on my breast.

Then, choosing courses for my first semester at college, I signed-up for an elective, Human Sexuality, which met right in the conference room of my co-ed dormitory. Led by a teaching-assistant, we just talked about one sexual theme a week in class and got two credit hours! And I met Dave, and I liked what he had to say, I liked how he looked. I invited him up to my room on the third floor after the third class adjourned. We made small talk; I was more nervous than when I interviewed to be admitted to this school. Getting a beer from my mini-fridge, I offered Dave one, too. I took a long pull on mine.

“I’m a virgin and I don’t want to be and I really like you…!” I blurted out. Then I felt like an idiot, blushed crimson.

But Dave was cool. “I’ll take that as a compliment,” he smiled, “though I find it amazing that you haven’t punched your V card yet; you’re so pretty.

Not many more words were shared before we were kissing and pulling each other’s clothes off and rolling around on my single bed. Soon I was aroused and Dave was aroused, and I asked, “How do you want to do this…?” He correctly interpreted this to mean what sexual position would work best.

“I’m an ass man and you’ve got an incredible caboose! Can we do it doggy?”

“I’ll take that as a compliment,” I joked and we both laughed. I felt a sudden jolt of confidence; males had been leering and commenting on my bubble-butt since puberty. I got on all-fours and pushed my bottom right up into his face. Dave actually kissed it before taking aim just below it with his erection.

“This is probably going to hurt you a little bit,” he confided.

“No, it’s not. I took care of my hymen long ago with a vibrating dildo. I’m a virgin in name only.”

“Oh, great!” He slid the big thing in with comparative ease and we started rocking and rolling. He grunted, “See? Now you’re no longer a virgin…”

“Not until we both climax,” I rejoined. In my head, I felt that the act had to be consummated to be official. After the initial rush as he entered me fully and possessed me deeply, it felt good, but not off-the-charts. The longer we did it, the more hum-drum it seemed. I so wanted it to be phenomenal, and it wasn’t. Pleasant, but not building toward orgasmic. Dave has hammering away, kneading my fanny flesh, huffing and puffing. “Are you getting close to…?”

“Yeah…” he said, sounding miles away. “You’re so tight, and wet, and you smell so good,,,!” He seemed to be getting closer to closing the deal with every thrust.

I wasn’t. The realization washed over me that my head wasn’t in the game, and never would be with vanilla sex. I was a freak. It felt wonderful for Dave to massage my cheeks roughly and I desperately wanted it to hurt. This wasn’t working, it was never going to work! I felt tears well-up. I wanted to scream.

“Stop!” I quietly commanded. With difficulty, Dave obeyed. I disengaged, got off the bed, and sprinted to the adjoining half-bath. I grabbed my favorite hairbrush, the one I used to beat a tattoo into my ass with frequently, the one I used the handle to rub out orgasms with right after each thrashing. I handed it to Dave. I didn’t trust him to use his bare hand hard enough to satisfy me. It occurred to me that if I got back into the exact same position, Dave might not get my message. So, I positioned myself over the edge of my bed, ass still offered up, but not quite so obscenely. I hoped it was just suggestive enough. Tears were threatening to burst through, there was a huge lump in my throat. Don’t ask me to explain, I silently screamed! I can’t say the words! Just take the hint…!

I waggled my ass about, then arched my lower back and thrust it out towards Dave. I looked furtively from the brush in his hand to my butt, back and forth.

“You… want me to…?”

I nodded, not knowing if he got the idea or not, but I needed him to do something. He reached toward my head. He was going to brush my hair. Couldn’t he see that there wasn’t a single strand of hair in those bristles? This brush was a well-used implement of ass destruction, not some grooming tool! I shook my head no and my ass affirmatively, both simultaneously.

“SPANK me!” I croaked through a constricted throat.

Finally, blessedly getting it, Dave tried to cover his mistake by circling his armed hand in a huge circle and swatting my proffered bottom a smarting blow. Yes, I wanted to holler! The sting made me retract, but I recovered instantaneously and arched my butt up as it had been. He gave me another swat. He got it! Now I was gonna get it. The storm clouds that had me socked-in lifted a bit.

“You can do it harder…” I whispered, still hoarse but with unbridled lust. He did. Dave gave me a really good smack. “Yes!” “…Just like that…!”

Having been given permission, Dave took ownership, God bless him. Without questioning my perversion, without needing further encouragement, Dave paddled my butt really nicely. My pleasure showed in areola that hardened down into tight little nodules of needy desire. I leaned on my elbows so as to take each in hand and pinch and pull and twist them. It was clear that my titty-torture hurt, and that I loved it. Dave saw that this was me, a very sexual person, but a very kinky one. He didn’t seem put-off.

“Do you think you could paddle my butt AND fuck me from behind simultaneously?” I asked sweetly. It wasn’t like I was asking for some super-human feat of agility, but actually more akin to asking if he could chew gum and walk at the same time. Yet with a huge smile of accomplishment, Dave did as asked.

“Is it… safe… I mean, in your cycle… or should I pull out before cumming?”

“Oh, it’s fine. I’ve been on the pill since I was sixteen to regulate my very irregular periods.”

Putting his gorgeous rocket back into my silo, I knew the difference instantaneously. Words gushed out of me, “Oh Yes!” “God, your cock is perfect!” “Spank me for all I’m worth!” “Oh, fuck!” “Fuck me!” My enthusiasm seemed contagious, Dave thrust into my tight sex with abandon, all the while keeping up a deliciously steady rhythm on my tight drum of a derriere.

Ultimately, the relationship was not a long-lasting one. It became clear to me that Dave wasn’t a spanko, and clear to him that I was. (“You mean, you want discipline EVERY time before sex?”) Just as my Grannie would repeat, “You can’t make a silk purse from a sow’s ear,” I would add that you can’t make a sexual maniac/kinkster from a vanilla, white bread, boring fart. But it accomplished what I needed. Not only did it add me to the rolls of fuckers, it confirmed that Shakespearean adage, “To thine own self be true.

”