***For the sake of anonymity, the names in this account have been altered. All other details are true.***
It was late 2001. I was 24 and enrolled on a series of internet dating sites. I received a message from a woman, Anna, a few years younger than me who had just recently graduated college. She did not have the best profile picture, but I had a pact with myself never to ignore anyone who messaged me. I hated it when I would contact a woman only to be ignored so I couldn’t do it to anyone else. I set up a date, and I was glad I did. Anna looked better in person. She had wide hips and a fairly large ass, but she was also quite tall, so she was athletically proportioned. We had a nice enough date, but there definitely was a disconnect in terms of our loquaciousness. I was always a talky kind of guy; Anna was more on the taciturn side. Still, after dinner she invited me to the apartment into which she had just moved. So new, in fact, that her roommate still hadn’t arrived. We started making out on her couch, and things got pretty intense in a short amount off time. I had two fingers nestled in Anna’s hairy vagina when she asked if I’d like to go into her bedroom. I did, and, again, so new was this apartment that while her mattress had been delivered, she had yet to put sheets and bedding on it. We did not have sex that night, but we did everything but. In fact, with Anna’s upside down pussy on my face, I slid my pinkie finger in her anus. She did not flinch from this and seemed to enjoy it. Anna gave competent head, but my orgasm occurred during a break while she was jerking me off. I distinctly remember cumming on her bare, brand new mattress.
We certainly had a good time sexually, and that hairy pussy of Anna’s was calling to me. I set up another date with her, even though personality-wise, we weren’t exactly a fit. I hadn’t met anyone else, so at that time Anna was the best thing going for me date-wise. I picked her up at her new apartment, and this time her roommate was there. Jen was a cute, blond cheerleader-looking gal from a small, rural town. Despite her small-town upbringing, she was quite well-traveled and worldly as I gleaned in just the first few minutes having met her. She had wooden sculptures from Eastern Europe that I had recognized, and she enjoyed showing me these treasures and telling me about the trip from which she obtained them, who purchased them, points of interest in the carvings. We had an instant connection, but, alas, I was going on a date with her less attractive (and less interesting) roommate, and Jen, herself, had a long-distance-boyfriend.
I put Jen out of my mind and when Valentine’s Day rolled around, still not having met anyone else, I asked Anna if she’d like to go out for the occasion. As I had later learned, Anna was having quite a lot of dates with other guys through the dating site on which we met, but whether I was her favorite out of the 3-4 other guys or the first one to ask her, she agreed to go out with me for Valentine’s Day. I picked her up again at her apartment and saw Jen once mare. This time Jen’s long-distance boyfriend was there. He was a nice enough guy, but he seemed kind of lazy and boring just lying on their couch the whole time. Not nearly worldly and sophisticated enough for Jen, at least as far as I was concerned. I remember quite specifically thinking, ‘You should be going out for Valentine’s Day with the roommate.’ Somewhat desolately, I took Anna out. We had a nice enough time and this evening we went back to my apartment. Perhaps because it was Valentine’s Day and our third date, when I suggested we have sex, Anna agreed. I did not know that Anna had been meeting multiple guys at this time, but something told me that it would be wise to use a condom. Only problem was I never had any luck with condoms. If I could even get one on, I would lose my erection during the penetration process (the condom robbing me of all sensation). Lo and behold, this happened with Anna. I attempted to penetrate, but lost too much rigidity with the condom. Two more times and three wasted condoms later, we gave up and engaged in our usual 69 routine.
Anna and I went out one more time, this time with a good friend of mine and his girlfriend (who would later become his fiancee and wife). This was probably the best thing for both of us because it opened Anna’s eyes. Anna – quite honestly – told me that she could not see us having as deep a relationship as my friend and his girlfriend, and we did not go out again.
Fast forward one year. I am at my local grocery store. There I see Jen with another young woman. I am not sure it’s her because I suffer from the ridiculous cognitive error in thinking that once two women live with one another, they will be roommates until one of them gets married. Since this other young woman was not Anna, I figured ‘Jen’ had to be a different woman grocery shopping with her roommate. So I didn’t say, ‘hello.’ Jen was quite sure I was the guy who briefly dated her former roommate, and came up to me and said, “I know you, you’re ________. You dated my roommate, Anna.” It was now that I learned she and Anna were no longer living together. I also learned that she was no longer dating that long-distance boyfriend lying on their couch a year ago. In fact, beautiful, worldly Jen was just playing the field. Not dating anyone in particular. ‘Well, add my name on the roster,’ I thought. I got her e-mail address.
Even though she gave me her e-mail, Jen had the same doubts most females would have about pursuing something with me. Would it hurt Anna’s feelings, who though no longer her roommate, was someone with whom she was still on good terms? Is it weird for a guy to make a play for the roommate? As I would alter learn, one of the guys with whom Jen was playing the field not surprisingly attempted to sabotage my chances claiming, “Oh, he’s just trying to pull off the Seinfeld Roommate switch.” Jen’s friend at the grocery store was an ally and endorsed me. She felt enough time had gone by since I last dated Anna, and it wasn’t as though Anna and I were ever in an exclusive relationship. Following this friend’s advice, Jen went out with me. We had a wonderful time. Jen was my match for loquaciousness. We both had a lot to say, many opinions. We decided to go back to my apartment. I thought for sure I was going to get to go down on Jen that night. It turned out she let me finger her, but when I tried to eat her pussy, Jen pulled away claiming it was too soon. Jen did not give me so much as a hand job though we hooked up until the sun rose. I had the worst case of blue balls I’d ever had the next morning. I was glad I at least tried to go down on Jen because I got to see her vagina. Bubblegum pink lips, trimmed though natural blond pubic hair, and just by looking at it I thought, ‘You may have found the vagina to end your pursuit of all other vaginas.’
We went out for dinner again and had a terrific time. Not much happened sexually, but on the third date, Jen took me back to her apartment, and fucked me. Why such coarse language? I endeavored to use a condom, and as usual, I lost my erection in the process. I tried another time, same thing happened. Jen said we could do it without a condom, and though I usually turned down those generous offers, I thought Jen was different. If she had a disease that would be the worst trick G-d could play on me. Here He answers my prayer of the preceding year when I said, ‘I should be going out for Valentine’s Day with the roommate.’ It was fate. I decided I would have sex with Jen without a condom because she was going to be the last woman I would have sex with at least until death do us part, and Jen got on top of me and rode my bare cock.
Nineteen years (14 of which as husband and wife) and three children later we’ve been together ever since that fateful first date in 2003.
Source: reddit.com/r/gonewildstories/comments/tohr3s/my_fortunate_sex_life
What a great story. Would love to hear more of you and Jen.