Gina Ch. 01

Story Info
Tommy loses his virginity & meets an older woman.
2k words
4.27
131.2k
22

Part 1 of the 10 part series

Updated 10/29/2022
Created 08/12/2006
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I was on my way home from my girlfriend's house, and I was furious. Well, girlfriend isn't quite the right word anymore. We had a huge fight and ended up breaking up. It started when I finally talked her into sleeping with me.

I had gone through the usual ritual, involving dinner and a show, some wine at her place and lots of kissing. At least I thought that was the usual ritual. I had been a virgin until tonight, and technically I wasn't entirely sure if what we did counted as sex. Maybe I was still a virgin?

After we had kissed for a while I started feeling brave and started touching her breasts. She had small, firm breasts, but I didn't get to enjoy them for too long before my girlfriend removed my hands. She wanted to just continue kissing, but I had other plans. I wanted this to be the night when I finally could say "hey, I'm not a virgin anymore".

I was 8 years old, the same as my girlfriend. I'd turn 19 in just about two months. I'm not what you would call a big guy. I'm 5'6" and weigh just above 140 pounds. At that time I weighed even less.

When she removed my hands from her breasts, I seized the opportunity to slide my hands down her petite body until I reached her thighs. Stroking her thighs, thinking I was a professional seducer, I whispered in her ear that I wanted for us two to go to her bed and make love. She tensed a bit, hearing this, but after a few seconds she kissed me and took my hands before she got up and led me to her bed. She laid down on it and just looked at me, smiling shyly. I knew that she was no virgin, but figured she still wanted me to take the lead. I took off her clothes, and even managed to unhook her bra, without her helping me. I marvelled at the sight of a naked female for the first time since I hit puberty. Not counting the numerous porn movies I'd seen of course. Then I took off my own clothes, while she still lay on the bed. My dick stood erect, thinking it would get its' first taste of pussy in just a few seconds. I lay down on top of her and kissed her on her lips before I tried to slide my hard cock inside her pussy.

"Wait. I want you to do something for me first."

That was the first words she had said in the last hour. "I'll do anything," I replied. Anything to get my dick inside you, the voice in my head continued.

"This is really embarrassing," she said, and hid her face under her pillow. "I want you to go down on me before we have intercourse."

"Of course I'll do that for you," I replied, smiling, while I asked myself "who the hell uses the word intercourse during foreplay?"

I had seen this being done thousands of times in porn movies, so I had a good idea how it should be done. I licked her pussy all over for a while before I finally found her clit. I inserted two fingers into her pussy, and started fucking her pussy with my fingers while my tongue licked her clit. My fingers went faster and faster in and out of her pussy, while my tongue remained its' slow pace on her clit.

Until now I had thought that licking pussy would be something that would make a woman cum immediately, but to my surprise she still hadn't had an orgasm after the first 5 minutes of this. 5 minutes turned to 10 turned to 30 minutes before she finally came, but when she came it was all worth it. She started shaking, clenching her thighs, pressing them hard against my ears, and her pussy squirted on me. This was the first time I had ever heard about a woman ejaculating, but it was amazing.

When she finally stopped cumming, she just lay there with a big smile on her lips, and I knew I had made myself worthy of loosing my virginity tonight. I climbed on top of her and she guided me inside her hot, wet pussy. I was so horny I thought I would come after the first two thrusts, but somehow I managed to hold on until I got used to the sensation of a pussy around my cock.

One thing I'm really proud of is my ability to hold an orgasm for a long time. Even though I was still a virgin I had masturbated for years, and had never been a fan of quick orgasms, so I had taught myself to hold my orgasm for a really long time before I finally let it go.

When I finally got used to the feeling of a pussy around my dick, and started fucking her for real I felt like a king. It lasted for a few seconds. I wanted to be able to grab her tits while I fucked her and figured I'd make my girlfriend get on top of me, so I asked her if we could change positions.

"Why do you want that?" she asked. "Can't you just do it like this?"

"I just want to try something else," I answered. Then I made the huge mistake of trying to make a joke. "You don't want me to be the only one working here, do you?" I said, referring to the fact that she had been on her back the whole time.

"If you don't like having sex with me this way, we can stop right now," she said then.

After this we both said some things that are best left unsaid, but it ended in a huge fight and we broke up.

I still hadn't had my orgasm.

So there I was, on my way home from my ex-girlfriend's house. I was furious and horny, and not quite sure if I was a virgin or not. On my way home I had to walk through downtown. There were a couple of strip joints there, with a reputation for giving extra service for a little money, and I was seriously considering the possibility of loosing my virginity that way when I heard someone coming up behind me.

"Aren't you a bit young to be hanging around this place, young man?"

I turned around and saw a woman approaching. I could feel my face turn red, knowing that it couldn't have been that hard to figure out what I was considering. I was standing outside one of the strip clubs, facing the door with my wallet in my hand, counting the money in it.

The woman was somewhere between 30 and 40 years old. She was shorter than I was, but it was clear that she weighed more than me. Since it was chilly outside she wore a big coat that hid her body, but it was still clear that she was a big girl. She had long blonde hair and a really pretty face.

I looked down, afraid to look her in the eye, and told her that I'd never been in a club like that before. I told her that I had just broken up with my girlfriend, and was on my way home now. Then I turned around and walked home. Fast. I did not dare to turn around and give her another look, although I wanted to. I was afraid that she would laugh at me, call me a pervert or even worse.

Nothing much happened the next week. I didn't try to get together with my girlfriend, even though my cock pleaded me to.

The following Saturday I went to a club with some of my friends. I had never been to this club before, but my friends had. They hooked up with some girls very early in the evening, and left me alone at the bar. I was watching my friends dance with the girls when I became aware of some girls sitting at a table. There were five of them and they seemed pretty drunk. To call them girls might be an understatement. They were all above 30 years old, and I recognized one of them. It was the woman I had met outside the strip club last week, and it was clear that she had seen me too. She smiled and winked at me while she took a sip of her glass. I smiled back, relieved that she wasn't shouting "pervert" and pointing any fingers at me.

I went back to watching the dance floor, looking for my friends, but I couldn't see them anymore. Then one of my friends came up to me from behind, making me jump and almost spill my beer.

"We're leaving," he said.

"That's cool," I replied. "But since I'm the only guy who hasn't found himself a girl yet, I think I'll hang around and have some more beers before I'll leave."

"Suit yourself. Keep an eye on the dance floor. There are lots of single girls out there," he said with a wink.

"I'll do that," I replied.

Three beers later I spotted the woman from last week on the dance floor. This was the first time I had a real chance to have a good look at her. Her hair was long, and she wore it in a ponytail. She had a white top that showed very much of her cleavage, and she had a short, black skirt on. She was dressed to get laid. I noticed that her tits were very large, and I felt my dick swell in my pants.

"Forget it," I told myself. "She's not interested in anyone your age anyway."

I drank some more beers.

"When the club closed, I still hadn't moved from my seat at the bar. I got up to leave when she approached me.

"Hello again, young man," she said.

"Hi," I said, blushing.

"I'm Gina."

"I'm Tommy" I answered.

"All night I've been thinking about sucking your cock."

At exact that time I took a sip of my beer, and it caught in my throat. I coughed hard, while she stood there grinning at me.

Play cool, I told myself, before answering. "I think I can let you do that, since you asked so nice."

Then she surprised me. Again. "I said I was thinking about it. Not that I'd do it. If you'd danced with me or something earlier tonight I might even do something more than just thinking about it."

She looked down at the bulge in my pants. Then she slid her hands down in each of my front pockets. Her right hand cupped my balls through the pocket while her left grabbed my hard cock. Then she kissed me. I could taste the alcohol on her tongue.

"Just think about what we could have done tonight. What you could have done to me tonight. How you could have used me, tonight. But you haven't earned it. At least not tonight."

Then she turned around, lifted her short skirt a bit, and grinded her ass against my hard cock.

"Mmm," she purred. "It feels so good against my ass."

Then she took a step forward, and I could see her bare asscheeks while her skirt slid down. It was clear that she wasn't wearing any underwear.

I looked down on my hard cock, and when I looked up again she was lost in the crowd of people leaving the club.

I put my hands in my pocket to try to hide the tent I had in my pants, when I felt something in my left pocket that shouldn't be there.

I left the club and waited until I was alone before I took out what I had found in my pocket. It was a white thong. Her white thong. Her wet, white thong. It had a phone number written on it.

(to be continued...)

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AnonymousAnonymous10 months ago

interesting story. it wasnt rushed . whats missing are characters the reader can identify with. characters that are real. personally im looking for that woman who isnt perfect. i prefer the flawed , imperfect person. the woman who isnt a pro at sex. i would revel in her ackwardness, as i perform in my own clumsy way

AnonymousAnonymousabout 5 years ago
Loose?

People don't loose their virginity they lose it.

Try to learn the difference between the two words.

AnonymousAnonymousover 17 years ago
great start

He damm well better go after her!!!

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READ MORE OF THIS SERIES

Gina Ch. 02 Next Part
Gina Series Info

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