Summer 2013

Things hadn't been going as badly since my last attempt with Dani, which I was chalking up to her just being a nut.

I'd started a new college program in January and I was absolutely rocking it. If my college had a Dean's List, I would've been on it. The pickings were slim in class though as far as women went, only two or three in the class.

I'd posted the odd personal on Craigslist, back when they still had those, but hadn't gotten any responses beyond the usual spam bullshit. Which brings us to the summer of 2013.

I was in my second semester at my new college and feeling pretty good. Then one of my Craigslist posts got a hit from a girl named Soofia. Naturally, I was wary of who I was talking to, but when after a few exchanged emails back and forth she didn't try and refer me to another site or anything, I figured she was probably real.

We met up in North York, the northern part of Toronto. I took my motorcycle, partly to look cool, and partly because it's harder to steal than a car, just in case. We bought a carton of fries and walked down to a park named for a former mayor, don't remember which.

We sat there for a couple of hours at least, just talking and getting to know each other. It was then that she told me she liked girls, but because she's a Muslim, she was looking for guys. When we decided we were done for that evening, we walked back up to where I had parked. Along the way, we had stopped for a moment, and I asked to kiss her. Soofia said yes, and there, on the streets of Toronto, we shared our first kiss.

The next time we met up, I picked her up outside her apartment in the evening in my car, Subaru Outback, nothing fancy. We wound up at the York University campus, where she had been a student, and she showed me around, telling me stories of her time there. We wound up on a blanket on the soccer field, and as we were talking she asked me if I wanted to kiss her, which, of course, I did.

She then said that we couldn't because it was Eid, and she had to abstain. I didn't quite understand, as I'm not a religious man, but I respected her faith and didn't force the issue at all. We actually had a good conversation about religion.

We met up a couple more times in her area again, once at York U again, during the Roger's Open (tennis) as she was a fan and former player, and once at a small park just down the street from where we first met. I'd gotten her on my motorcycle a couple of times at this point, and she seemed to really enjoy it.

The next time we met up, I don't remember the circumstances of, but I had picked her up and brought her to my area, about an hour's drive/ride each way. I know it was the weekend, because my parents weren't home. We made out for a while in my room before she took her top off. I spent a while caressing her breasts as we kissed, reaching inside her bra to play with her nipples.

She sat up and asked me to take her bra off, but hard as I tried I couldn't unclasp her bra. She took pity and did it for me as I kissed her back, neck and shoulders. She lay back down and I fondled her tits unencumbered now as we made out, eventually working my way down her body to kiss and suck on her nipples.

At one point she got on top of me as we made out and ground herself on my obvious erection. When I made a move to undo her pants, she broke the kiss and told me no. We kept making out, with me grabbing and caressing her ass through her jeans. I tried a couple of times to feel her ass under her jeans, which upset her a little bit, and we eventually stopped.

She told me she was going to go to the bathroom, and I had two choices. I could take her home, or I could get naked and masturbate for her when she got back. She got up and left, and I shucked my clothes. I didn't know if it would lead anywhere or not, but I figured I should keep the sexual activity going however I could.

When she came back and saw me sitting naked on my desk chair, she smiled and lay down on the bed on her side facing me, and watched as I masturbated. She stroked her breasts and pussy through her clothes a few times as I did. I admit I struggled to cum, as this was the first time someone had seen me naked, but I got there. And soon after took her home.

The next time we were in my area, we went down to the lakeshore and sat by the water, talking and making out. We decided to stop by my place, and we hung out with my parents for a bit before going to see a late movie. Eventually, we made it back to my place and in my bed again.

While I lay on her, I leaned back into a kneeling position between her legs. She was topless again at this point, her breasts heaving from the heavy making out we'd been doing. I reached out and began undoing the belt on her jeans, and Soofia again said no, but this time made no move to stop me.

With her belt undone, I held the clasp of her jeans and looked at her, waiting to see if she'd confirm that I should stop, or let me keep going. She smiled and lifted her ass off the bed, and off came her pants, leaving her in just her panties.

I went back to kissing her, slowly making my way down her body to her panties. I pulled them off her body, then kissed my way up her legs to her pussy. She asked me at that point if I had a condom, and I said no, so she reached into her purse and pulled one out. She had me get undressed and we out the condom on together. 

She wanted music, so we went to my computer and selected a long playlist on youtube, she was standing naked beside me, as I sat naked on my desk chair. Once we had the music selected, I turned the chair to her and tried to pull her onto me, but she said not on the chair and we moved back to the bed.

As she lay back, I got between her legs, and went to finally insert myself inside a woman, when Soofia said no. I was not allowed to go inside her, ever. She'd had dick before, but even though she'd cum, she didn't like it. She said I could eat her out, and she would jerk me off. I asked why the condom and explained that she didn't want to touch my semen or precum.

I wasn't about to turn down what was in front of me, so I began eating her pussy. As she bucked and moaned, she told me to lay on my side so she could jerk me off. After making her cum a few times, she had me on my back and focused on getting me off. Unfortunately, I was too used to doing it myself and she couldn't get me over the edge. I wound up having to finish myself off for her. It was still an amazing experience, and in the afterglow, we held and kissed each other.

From that point on it was open season, we had our version of sex at my place a few more times, including having her spend the night with me, and having the "most passionate sex" she'd ever had after an argument in the morning. We did it in the back seat of my car in an alley after spending the evening at a lesbian bar. We even did it in parks, with me on my knees between her legs as she leaned on a tree, or both of us on a blanket with just our pants undone and rubbing each other as people walked by.

Eventually, the cracks that I had ignored in favour of having someone in my life began to widen. She didn't want kids, I did. She was seeing other guys while we were together, and was honest about it, but made it clear she was not my girlfriend as she was keeping her options open. She said I would never be allowed inside her in any way, no blowjobs or pussy, which ate at me, though I tried to rationalize it was better than nothing.

She didn't like that I wasn't at her beck and call anymore now that I was working part-time during my off semester in the fall. And I didn't like that I had to drive an hour each way to pick her up and bring her back to my place, and she wanted no part of me in hers.

In the end, things collapsed when she went off at me over text while I was helping my mom with some grocery shopping. My frustrations boiled over, and we argued before saying, "fuck it, we're done." Just like that. While it was the best sexual experience of my life, it was also incredibly frustrating, and the end did have an impact on me. I was more convinced than ever that nothing would ever happen for me.