[M] My 2nd time with Jess. The girl I can’t stop thinking about.

The first story – https://www.reddit.com/r/gonewildstories/comments/3idkek/m_story_of_my_first_time_have_told_only_a_few/

Please read My first story about this same girl linked above which details my first sexual experience and the beginning of my relationship with “Jess” (“names have been changed…” and all that). This was never intended to be more than just a story about my first time. But now that I’ve written it all out and relived some of the moments it makes me think of many of the times I’ve spent with Jess since then. My feelings toward her are more complicated then I have let myself realize. So maybe this can be a bit of therapy for me while being something interesting and sexy for you to read. I promise there will be less context than the first story and more good stuff (SEX!!).

After our weekend in the Adirondacks we kept in touch. I kind of went to college for a year, she went through some stuff but we finally both landed on our feet in different towns. One night after losing a job I didn’t like I was feeling down and she was the first person I thought of. So I called her, she cheered me up a little and invited me to Rochester (This is not actually where she lives, I just figured I’d be safe). I liked the idea and since she had been sending me a lot of pictures, some naughty, I had been spending a lot of time fantasizing about her. Also she was my first, and was better than most girls I had been with since then. So, jobless, I head off to see her again, this time with plenty of condoms.

I finally find her apartment, it’s late, I’m tired and I’m glad to be out of the car. I hear her unlock the door but it doesn’t open. She calls from what sounds like a distance to invite me in. I walk into her living room and there she is, on the couch in black lacy lingerie with garters attached to thigh-highs and those amazing boob barely fitting into a corset. By now I was less timid with girls so I went for it. I pulled my shirt off on the way to the couch then started kissing her like I was auditioning for a part in an action-romance movie. As much as I love that piece of lingerie (I’ve seen it a few times since) it is a pain to get off. We did our best to not let it kill the momentum. Next thing I know we are standing up naked, kissing and groping at each other. Let me tell you something about her ass. It is like the sexiest, most pleasure inducing stress ball you can ever imagine. Grabbing that thing has added years to my life. I was feeling bold so I turn her around and bend her over the couch then get on my knees with her ass in front of me and her fine pussy hiding between her legs. She got the idea and spreads her legs while I gently stroked her lady parts. I spread the lips a little and give it a lick. I circle my tongue around, being careful not to touch her clit yet. When I press the flat part of my tongue into her whole pussy she presses down a little and I feel her hips start to gyrate and feel a big sigh leave her lungs. I love this moment when you know a woman is starting to get into it. This continues for a while and inside I’m celebrating because this is one of the many things I had fantasized about doing to her.

Now I’m on my back and she grabs my cock and I have that surge of ecstasy when you’re cock is confidently handled by your woman the first time during sex. She strokes up and down, and examines it a little before finally leaning over and putting her sweet lips around my incredibly hard cock. I feel her tongue press against my tip before sliding her mouth slowly down the shaft and back up, one of the best feelings in the world. She cups my balls while she gives me head, stopping occasionally to catch her breath or wipe some spit off her chin. I know I’m not going to last (remember, I’m still young and hadn’t had a long tenure in the world of sex). I ask if I can cum on her. At the time I didn’t know if this was too weird or kinky but she doesn’t seem to mind. In fact, she got a little excited and when I told her it was time she got in position on her knees with one forearm under her boobs and the other hand stroking me hard and fast. I moan quietly while I let her do the work, then I squirt my warm cum on her chest. Some of the first stream went over her shoulder but she readjusted and pointed closer to her boobs and the rest hit her right where it counted. It was a lot of thick white cum, I was young and I had a lot to give. She laughed and looked down at all her hard work. I follow her to the bathroom and watch her clean up. I study her naked body, watching her move, enamored with the way she looks, even better than she looked when she was 18 in that cabin. She wants to lay in bed together and I do too. We spend the rest of the night talking. It was getting close to morning now since I had driven a long way from home. We fall asleep together and wake up in the afternoon with bad breath, felling a little sweaty from having slept in each other’s arms. And these moments – despite how unsexy they are, despite how great the sex was – these are the moments that I remember most fondly. We would have many more of these moments, times when one of us needed the other. Maybe we were just feeling horny enough to make the long drive. But we have never had a romantic or traditional, boyfriend/girlfriend relationship. Even though those late nights with her are some of the most romantic times I’ve spent with a girl. We did have more than just oral sex that day. It was not fantastic sex. Maybe we didn’t know each other well enough or maybe we weren’t experienced enough. But it was fun sex.

I recently broke up with a longtime girlfriend. It was long overdue. And it all started with How I Met Your Mother. The story involves Jess and sex. I would love to share it if you are interested.

Source: reddit.com/r/gonewildstories/comments/3if6zw/m_my_2nd_time_with_jess_the_girl_i_cant_stop

5 comments

  1. Love these stories. Reminds me of my sheltered childhood. Have you talked to her recently? How does she feels about you?

  2. I would enjoy hearing the rest of your story. . . . .hoping that you end up with Jess. . . .

Comments are closed.