This story actually happend with my second girlfriend and looking back this is actually a bit funny, since everybody knew what was going on that afternoon. Once again sorry: English isn’t my native language.
It was right at the beginning of my sexual life. I had a girlfriend before, but we’ve never gone further than petting, since she was afraid of my dick.
It’s a bit funny since I’m just average in lenght and maybe a bit above in girth, but both of us were virgins and before she became confident we sadly broke up.
I actually remember the situation quite well (who doesn’t ? It was one of my first sexual experiences): We often met at her place cause her parents were divorced and she was living with her father who also worked on weekends.
We kissed and cuddled before and I’ve already seen her nice boobs (with the darkest nipples I’ve ever seen in my life), but we never “touched” eachother. One day she went for it and unbuttoned my trousers, she was unable to get my dick out, so I did it for her, took her hand and let her feel it.
She had never seen a hard dick before and was also very afraid to touch it at the beginning, especially because im partially cut and seeing my entire glans on top somehow made her uncomfortable. Out of my own interest and also to make her more comfortable, I opened her shorts and she shown me how to please her clit with my fingers while she was giving me sort of a handjob (it didn’t really worked out cause she was so afraid to make something wrong). I just touched her pussy and clit back then but never completely put her pants of, so I only touched but didn’t seen her down there.
But I couldn’t get her comfortable and so this was the maximum of our sexual experiences. I remember that I had to stop on my way home (which went trough a forest) to jerk off because I was so damn horny and still had a boner for hours.
So my second girlfriend took my virginity, which wasn’t really a very nice act. She wasn’t very confident and experienced, but not a virgin anymore. So she just “let me do it” to make me happy.
We had some petting for the first time and were laying on her bed. She already had my dick out and was giving me sort of a handjob. I tried to please her the way I’ve learned from my former girlfriend.
At one moment she asked my if I was still a virgin, I was a bit ashamed since I knew that she wasn’t anymore. She smiled and tought that we should do something about it. So she handed me a condom, I put it on while she spread her legs wide open and so I just went for it.
I didn’t realized that she was incredibly tight and so I just rammed my entire cock inside her, not really knowing what to do. I wasn’t watching her or her body, this was my first time and my head was spinning. I came very quickly and that was it: I wasn’t a virgin anymore…
Looking back it was a very selfish act and with the experience I have today, I feel sad about that because this could have been much more for her. I also immediately thought this after it was “done”.
She never said anything, but I knew that this wasn’t a very enjoyable experience for her and I was certain that because she was so cramped it also must have hurt her.
So I just wanted to give her something back as soon as we were together again, but this was no easy thing. We both still lived at our parents places, in her case that was a small farm where they were doing agriculture.
This made it complicated for her to visit me in my place, since she had to help out in her free time and we couldn’t do much more at my place because my parents were around most of the time.
We mostly saw each other on the weekends, but because this was a farm, most of her and her brothers friends were around, so having some time on our own was again hard to get. Also her brother liked to party the entire night, what made our privacy even more complicated.
She had her own bedroom on the top floor of the house, but sometimes even that was no option to get away from it all, without anybody randomly showing up.
One saturday afternoon we were again a big crowd, having fun at the farm and enjoying the summer. She was doing something for her parents and I was waiting for her to show up. When she finally came by, she was all sweaty and exhausted. The only thing she wanted was to take a shower…
So I asked in front of everybody who was around, if I could join. I don’t really know if anybody really bothered, but asking this in front of a bunch of teenagers may be a bit offensive, but she agreed and so we went off.
I just wanted to be as nice as possible to her and give her the most pleasure I could offer with the little knowledge I had at that time. I had a raging boner right from the point on when we went into the shower, but I put my ego back and wanted her to just enjoy the shower and relax.
She was a bit chubby, but had an extremely nice face, a lovely smile and some absolutely gorgeous boobs. Her skin was always a bit pale but it fitted her blonde hair and the green-grey eyes. She was almost exactly the same height as me. Ignoring how absolutely damn horny I was, I started creaming her body and her hair, rubbing her back, providing some small kisses here and there and she seemed to like that very much.
I think this went on for about quarter of an hour, nothing really sexual or naughty happened. Then she kissed me: Just a simple kiss, without tongue and she just slightly touched my still raging boner without doing anything further.
I grabbed a bit of soap, but it between my hands and started to rub her thighs, she spread her legs a littlebit and I gently went along the outside of her labia. I didn’t touch her clit or went inside her. Just giving her some simple, nice, gentle rub around per pleasure zone.
She let me do this for a minute or two and then whispered in my ear, that we should go upstairs into her bedroom. So I took a towel, rubbed her dry and put on my shorts. After that I went for her bedroom while she went off to get us something to drink.
When she came back into her bedroom, only wearing a towel, I stood up and just gave her a nice hug, kissed her on her mouth (without tongue) and released the towel. This was my chance to give her back what she deserved: I just whispered in her ear, that she should lay on to the bed and let me do the rest.
She looked a bit shocked and I ensured her, that I’m not simply going to put my dick into her. She laid down a bit nervous and was a bit astounished, when I didn’t show up but instead started to kiss the inside of her thighs.
I had no idea what I was really doing, the only thing I knew was: There is that clit and that pussy and somehow I can please her by using my fingers and tongue on her. So I went upwards with my kisses and arrived at her pussy. I took a finger and started to look for the clit, It took me a minute to finally find it and I pushed slightly against it.
Her lips looked a bit like swollen, but I was fascinated by the first proper sight of a pussy. Her clit was hidden behind her inner lips and could only be found by touching it gently, but it was able to find her little pearl !
She moaned and I knew that this couldn’t be wrong. I also realized, that the window was open and everybody outside could hear us, but stopping now was no option ! So I replaced my finger with my tongue and started licking her clit. At the beginning I was very gentle, but soon realised, that she moaned even more, when I pressed it a bit.
As we were both just a the beginning of our sexual experiences, we handn’t shaved ourselfs. So my nose was deep down in her hair. But it was really okay, since I could still smell the soap we used in the shower and I just enjoyed been between her legs.
Her pussy got massively wet and I had to convince her, that this is no problem for me, I have to say: I was fascinated and it gave my confidence, that this was the right way to bring her to climax. After a while I gently startet to again massage her lips with my fingers and at some point I gently started to stick one in her hot, wet hole.
She seemed to like that, but the inside was extremely thight. I moved my finger really gently against all sides, still pleasing her clit with my tongue and sometimes my other hand. I gently tried to widen her tight pussy with my finger by gently pushing it in all directions and it worked.
I was able to put a second finger inside her and her moaning became louder and more intense, I had only one goal: Bringing her to explosion, ignoring how damn horny I was and that my cock was rock solid for quite some time by now. She started to move more and more and her breathing was getting heavier, then she said “please stop, I’, going to explode”… I didn’t
She went of like a rocket: Her entire body tightend up, her breathing was heavy and fast and I it felt like she was pressing even more juice out of her now softened, widened pussy. She took her pillow over her head but everybody heard what was going on.
This went on for like a minute or two, her body was as tight as it could be, every muscle seemed at its limit and I wanted it to go on for ever. Altough this was hard work for me (especially my tongue) I was also in heaven: I was able to give her something back for what she had done for me.
She rolled back and forth, from side to side and I just didn’t stop pleasing her, it was so worth the effort !
She grabbed my hair and pulled my head towards her, kissing me as passionately as possible. We cuddled for a couple of minutes, while I still slightly massaged her pussy and boobs with my hands. As I’ve said before: She had really decent sized boobs and I haven’t seen her big, round nipples that hard before.
Then she wanted to move on, turned me over and went down on me. I didn’t expected that to happen and I felt a bit guilty: I didn’t wanted her to do that because she felt she had too. I immediately told her that and she started to giggle: “I have no idea how this turns out, I’ve never done that before”, holy s… this was getting better and better.
So she grabed my dick, pulled what is left of my foreskin back and just put it in her mouth, then we both laughed, this was not working well. I told her to grab the bottom of my shaft and gently move the skin forth and back while sucking on my glans. It made me extremely horny, but I didn’t reach climax and I didn’t wanted to come in her mouth.
She was a littlebit dissapointed, but I didn’t mind and so she started to give me a handjob, this only took a minute and I exploded all over her sheets. I was just pumping my cum out in streams like never before when I did it to myself. We both laughed hysterically as her sheets where now completely ruined by her juices and mine, everybody could hear what was going on in our room. We were both sweaty and messy.
For some time we were just laying there, kissing each other and cuddle a littlebit. Then she once again grabbed my dick and said out loud “know I want to get fucked properly”, I almost instantly had a rock hard boner… I grabbed a condom from her bed table and started again to rub her clit, she was already hot and dripping wet again.
So I simply went on top of her, the good old missionary position. I didn’t wanted to rush this again, so I first checked out her pussy. Altought it was hot and wet, it was very tight again. So I had to use my fingers once more, before we could start with the main course. The trick worked as before and I slowly was able to enter with extrem caution not to harm her.
This time I noticed many more details than the first time. I had to move in and out very carefully, because she was just so damn tight. I now noticed how her lips enclosed my dick all around and how wet and hot it was inside her. And now I could also see her clit that was normally a bit hidden, I started gently rubbing it.
Because she was so tight and wet, even when moving slowly it made a noticeable slurping sound, we didn’t mind…
So for the first time, I really saw the entire women laying in front of me: Her big boobs slowly moved up and down in sync with my motion, her eyes were closed, the head rolled to the side. She was sweaty, breathing harder and harder and there was a bit of a smile in her face.
As I had already jerked of quite extensively before, I was able to bring her to climax once again by gently moving my dick inside her while rubbing her clit. I somehow was a bit nervous to not come before her and this had the opposite effect, so it really took me some time to come. Also I didn’t really move much after she came, since it was getting a bit more tight in there.
I didn’t came as hard as before, simply because my head was spinning now, but it was very nice that this time it had a happy end for both of us.
I gently pulled my dick out, lay next to her and we kissed each other. We were both in heaven, exhausted but totally happy, cuddled for some more minutes and then went down to our friends… nobody said anything.
Source: reddit.com/r/gonewildstories/comments/5qcrjy/my_first_time_properly_pleasing_a_woman_and