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View Full Version : My first time, from shy to sly



Purple_Monkey
02-06-2010, 05:58 PM
Hello and thanks for reading this tale. Allow me to relate my first sexual experience with you, I hope you will enjoy it as much as me writing it.

I grew up in a rather strict and conservative house. As a result I never had a girlfriend during my years at school, I was just too embarrassed to introduce a girl to my parents. It doesn't mean that I didn't know anything about sex, I had a older friend who shared all sorts of info with me, he also had a stack of “saucy” magazines,(at that stage our country had heavy censorship, you were allowed to kill kids for complaining about language in school, but heaven help you if you see a nipple in a magazine).
I started masturbating at an early age, and my fantasies became wilder and more realistic as I grew older. However, my actual experiences of a sexual nature was limited,
- During my final year in school I touched a girl's butt, we were in the maths class with the teacher out, she commented on my ass, ran her hand over it and invited me to do the same. Feeling quite daring I slipped my hand underneath her skirt and touched her ass.
- A year out of school I touched a girl's breasts during a truth or dare game.
- At a movie evening me and a lady friend were sharing a duvet and she allowed me to touch her breasts.
- A very pretty girl with very nice boobs showed me her new bra, providing me with masturbation fantasies for quite some time, although I was a bit sad that I was treated as the gay harmless friend with whom such things could be shared with.

So, by the time I was 20 I was rather sexual frustrated, my friend already had 3 steady girlfriends who he screwed, and I couldn't help to feel sorry for myself. At that time I had a close lady friend, we chatted and shared almost everything, I liked her very much, but she made it clear that she simply didn't see me in a relationship way. I knew she was sexual active, in fact she screwed 2 of my friends at that time. Our encounter occurred on our second movie evening, the first time was actually the perfect timing, we were all alone, the second time my brother and sister was in the house.

What usually would happen was that I would pick her up, we would get some pizza and movies, at that time still videos, we would drag a mattress into the TV room and would lay in front of the TV watching movies and drinking wine. Earlier that evening played with some rub-on tattoos, she put one on my back and she lifted her shirt so that I could stick on to her back, revealing her bra straps. Later on we were in front of the TV, watching movies. In order to get comfortable we ended up with me on my back and her on her side, her head resting on my shoulder. This causes my arm to be uncomfortable and I rested it on her hip.

Now, believe it or not, without em registering what I was doing, I slipped my hand underneath her pants and panties ans started to stroke her butt. I only became aware of it when she turned to me and said told me, “You are making me horny.”When she said that I realized where my hand was, I started to retract it but she indicated that I shouldn't, instead she turned on her back and placed my hand underneath her shirt on her tummy. I quickly moved my hand to her breasts, pushing her shirt up until her breasts were exposed, she had removed her bra earlier because. I cupped one breast in my hand, ran my thumb over the nipple, taking in everything I saw. Then I moved my hand down, across her tummy and into her pants, feeling the soft curls of her pubic hair and finally the soft folds. I explored with my fingers, found her opening and slipped my finger in. She was moaning softly and moving her body, when my finger entered her, she pushed with her hips and took me deeper inside. I moved my finger in and out, changing the tempo from time to time. Meanwhile she had reached into my pants and curled a hand around my penis, squeezing and jerking it. After a long time she turned to me again, this time whispering in a shy voice, “I want you in me.” I had no problem with that and asked her to remove her clothes. I dropped my pants and knelt between her legs. I asked her to help me, she took my penis in her hand and guided me into the warm, tight opening. It took me a bit, but soon I had a rhythm and was moving. She raised her legs and placed her hands underneath her knees, she was also squirming underneath me. Of course just when I started to enjoy the sex, my brother or sister made a noise and I quickly pulled out and dived underneath the covers. Whoever made the noise did not pass the TV room, but the mood was broken and she was dry, I simply couldn't enter her anymore. We didn't had any lubricant ready and didn't know that spit would help.

So we went outside for a smoke, where she complained that she didn't actually wanted to have sex with me because she saw me as a friend and now everything would change. We didn't do anything the rest of the evening and the next morning I returned her to her home. The Monday we returned to the collage, where we both studied. She was staying in the residence, I drove through every day. On out way there we didn't talk about what happened, there was other people in the car. However, later that day between classes, I met her in the cafeteria, where she asked me to take her to the Union buildings, which had a huge garden, more like a park. We found a nice secluded spot and then we discussed what happened the weekend. She made it clear that although she enjoyed it, even though it was against her principles to do it with a friend. I told her that our friendship was strong enough to handle sex, we can be fuck buddies if she wanted to be and nothing will change.

(Yeah right, everything changed the minute I slipped my finger into her, we both knew it. I would say anything to get some more and it didn't take too much to convince her.)

She told em that I should learn to kiss, we didn't do it the last time and kissing was important to her. So the rest of the afternoon we with her teaching me how to kiss. During this time I had my hand underneath her shirt, playing with her breasts, I slipped my finger into her and she gave me a hand job.
We returned to collage , since I still had some classes, but we agreed to meet after my classes for some sex. I simply couldn't concentrate in the class, I kept thinking on what would happen afterward.

Now let me tell you quickly about this girl. When she was 16 she was in a lesbian relationship for a year. Although she enjoyed the relationship, she just wasn't sexually satisfied. She broke up with the girl and not long after had her first man. From thereon she would hang around the local nightclubs and party places, finding a guy she would fancy and then screw him, usually one encounter only, before moving on to the next guy. She did had a few relationships, but she mostly enjoyed the thrill of the hunt. She had a very skinny body with small breasts in a country where large breasts were considered the norm. Her body embarrassed her, so despite her numerous sexual encounters, very few guys actually saw her naked, or even her breasts. I was the first guy who saw her totally nude from the beginning. She also didn't had time to learn much, nor did she care, later I had to teach her how to pleasure a man.

After my evening classes we met outside and discussed where we should go. The campus had tight security and we couldn't risk getting caught screwing. We were both poor students who couldn't even afford a hotel room for a night. Finally I pointed out that the top floor was still open, the building was only locked at 10 every evening, but there was no classes at that stage. So we went to the top floor ladies room and entered on of the stalls. I sat down on the toilet and she sat in my lap. We kissed and I moved my hand up and down her clothes. Then she ordered me to strip, I complied and sat down nude on the toilet again. She then performed a small striptease, removing her jeans and blouse. Underneath she was wearing a lace camisole, a bra and panty set that was made from silk but had lace trimmings. Everything was white. She had changed her underwear to hide her body, but my eyes were like a kid looking at a Christmas present. We kissed and I slowly removed her lingerie, then kissed her breasts and sucked her nipples. My penis was hard as a rock in her hand. Finally she mounted me, taking my cock into her and started to move. I tried to move with her, but she pushed me down and told me to sit still and enjoy. So I remained still, watching her face, watching her breasts moving, I placed my hands on her buttocks and enjoying getting fucked by her. Surprisingly I took some time to come, I suppose the hand job earlier helped. I warned her I was going to come and she told me to come inside her. So I came inside her. We spent some time kissing some more and then she cleaned up and we got dressed again.

The Thursday was a public holiday. She was back home. My parents were going out the morning, but would be back later in the day. I phoned her and told her we had the house too ourselves for a bit, if she was interested. She told me to pick her up and I quickly raced over to her house. Back at my house we didn't waste time, we went in my room and immediately grabbed each other, kissing and undressing. I kissed her and moved my mouth down, kissing her breasts, kissing her stomach and finally my head was between her legs. I started to kiss the insides of her thighs and then moved my mouth to her pussy, kissing and licking, not quite knowing what I was doing. She squirmed and moaned and begged me to fuck her, so I did. After wards I ran a bubble bath and we spent some time in the bath, before I returned her to her house.

That was the beginning of out relationship. In that first few months I made up for my lost time as a sexual active man. She was a very willing partner and we learned new ways together. We bought sex toys and lingerie, we tried various positions, we screwed in numerous places. She had moved from the campus into a lodging house, where security was not as tight and we could spent evenings together. We couldn't get enough of each other. Even now, several years later, we still have fun, although the tempo did decrease a bit.

And that was my first time.

Saffer
02-06-2010, 11:16 PM
Nice story. Needs a little bit of editing, but otherwise well written, and from the heart.

Lucky you that you managed to make it work with the friend!

phogga
02-07-2010, 10:15 AM
Nice enjoyable story

weezway
02-07-2010, 01:06 PM
nice story

surfguy17
02-07-2010, 02:51 PM
cool story

OldHorny
02-07-2010, 04:03 PM
Thanx for the addition enjoyed the read ;dvl

frankjohnmoore
02-07-2010, 11:39 PM
nice story, thanks

Purple_Monkey
06-19-2010, 07:54 AM
I am glad you liked it. Like most of my stories, its based on a true events.

loobinator69
04-01-2012, 07:24 PM
nice story, maybe you could elaborate on the sex instead of "she begged me to fuck her, so i did"

smoothshy
04-01-2012, 10:02 PM
Good story, though I agree with loobinator