I have (kinda).
When I was in my last 3 months of college, my girlfriend of 2 years and I had a tough series of discussions to decide what to do when I graduated and she would continue on for a master's degree. I knew I couldn't stick around the school since there were no jobs for me there, and we had a tough summer previously staying in touch and keeping up a long distance relationship. She even had one guy hound her every single day at work, making sure he was the first to know when we finally split up. We decided that since things couldn't easily continue, that we aught to spend the last few months together as friends, adjusting to the other as single people.
That said, we stayed friends with benefits.
I had a tough time initially trying to get my confidence up. I started confiding to a mutual friend of ours. She can best be described as a tomboyish lesbian with a curvy figure at odds with her manly attitude. She was short, with a pageboy haircut, wore glasses most of the time, and never wore makeup. Below the neck though, she had a killer set of both T's AND A, which at parties she had no qualms about flashing. She could be a flirt when she had a drink in hand, but always defended her lesbian honor, saying she hasn't had a man since she came out some 4 years prior.
In these late night AOL messenger conversations, I would complain at my inability to flirt in person. Every time I'm talking to a girl i'm interested in, I'm either completely honest and spill my guts, or I clam up and don't get the courage to let her know I'm interested. I've only been with 2 girls before; my most recent ex and my highschool girlfriend. She too was going through a breakup. She had a butch girl who lived some 2 hours away, and was tired of being stood up on their date nights. One fateful night, at about midnight, she calls me (or I messaged her) after we both got stood up on a date. We were both so frustrated, the conversation turned immediately to sex. She hadn't had any for weeks, and I was questioning if I could be with anyone else at all.
She was the first to mention that she had thought about swearing off women for a while. "Celibacy?" I ask. "No, I mean try cock again." she replied. "Well, I'm free tonight." I respond with all honesty. "You sure, like, you want to give this a try?" "HELL YEAH!" I didn't type that last part so very enthusiastically, but I thought it that way.
Unfortunately, though it was past midnight, we couldn't meet up immediately. I had no car, since I lived on campus, and her house was nowhere near the bus line. She offered to pick me up once her housemate got back in touch with her. The minutes dragged on, and I feared that there was no chance of it happening that night. at about 2 am, she calls me and tells me to meet her out in the parking lot. I hop to my feet with all speed and run out into the cold (It was October in the mountains. I forgot how cold it got that time of year.) I waited for about 20 minutes, each passing minute making me feel more foolish and expecting her to cancel, but she eventually pulled up. I hopped in the car. Though I was pleased to see her, I was honestly let down by her apperance. She had just hopped out of the shower, it looks like, and was wearing a sweatshirt and jeans. I've heard of casual sex, but this was taking it to the extreme.
On the drive to her place, we discuss what the night is going to be about. "I'm not sure about fucking right away," she said, "since it's been so long. I want to work up to it, if you know what i mean. And when you go down on me, I expect you're going to do it like a guy, so I'm sorry in advance if I have to show you how I like it." I nod and agree, not quite knowing what to say. We get to her house, she takes me upstairs, whips off her clothes, and gets me to do the same.
I'm sorry, dear readers, but this was getting to be close to 3:30 am. I remember first some kissing, then working my way down her neck (which she loved) to her tits (which I loved) and then starting to eat her out. I had only been with two girls, true, but in both cases delayed intercourse for months before taking that step. She told me I was very skilled with my lips and tongue, and that I ate pussy like a girl (a compliment that I have received since that night). She was critical, however, of my fingerwork, and taught me to use my whole arm, biceps and forearm, to finger her roughly after quite a warmup. I gave it a shot, and got her to a quivering orgasm.
Unfortunately, she couldn't quite handle the rush of hormones so late at night. When she pounced on me for my turn, after just 2 minutes of trying to suck me off, she appologized, and said she just can't handle any more. She said as i was making her cum, she could only think of her girlfriend and that it was giving her a panic attack. She wanted though to make it up to me. I asked if she wouldn't mind posing for some dirty pictures. "Of course!" I got out my camera and swore like a motherf*cker that it was out of memory. She offered to let me stay the night (downstairs on the couch) and she would give me a ride back in the morning. I'll admit, though i was horny, i was also dead tired, and took up the offer.
The next morning, I woke up, she made breakfast, and we talked quite distantly. Just when I thought it was safe to talk about the night before, another friend of ours, a guy, knocks on the door. She told me to let him in as she went to change. He was surprised to see me at her place so early in the morning. He asked if my girlfriend stayed the night. That's when I was about to break the news to him that the constant couple was no more, and we were splitting up. Before I could answer, my tomboy friend comes downstairs and says "He was just leaving" and ushers all of us out the door, we pile into her car, and she drops me off before they head to something or another.
I thought I had totally fucked up. The first girl i hook up with is a mutual friend, a lesbian, and to tell the truth, bipolar. I'd seen her bad side and knew I was going to be on the receiving end (no pegging pun intended)
But, surprisingly, she liked the encounter, but didn't want to rush it again until my gf and I had made our breakup public. We would have a few more flirty nights, but sadly wouldn't get down and dirty 'til after I graduated. But that's another story. And that night, my camera was ready....
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