I don’t remember why, precisely, I had gotten so desperate. It is weird how life provides such interesting periods of up followed by sudden periods of down. Whatever it was I was in the middle of was definitely a down period. I had ended things with my FWB about a year before. I had dated someone who was not right for me for a few months and let some bad shit affect my life. I was starting to put things back on the right track and my first sexual foray was not one of my proudest.
I had met a girl on OkCupid — I think — and we hit it off pretty well. She lived really far away in Boston, so I didn’t think there was much of a chance or reason to pursue things. We chatted for a while and she was pretty cool though. Very smart, very pretty, very witty, and very interested in me for some reason. One day things changed when the conversation got sexual. She sent me some nude photos out of the blue and I started to reevaluate my position on going to Boston. I’d never been there before and this seemed like a pretty good reason to make the trip.
We coordinated things and one long weekend I booked travel and headed there to meet up, stay with her, and have a lot of fun. We were going to tour around and we were certainly planning to fuck a lot. We had both been single and sex deprived for a few months so this was naturally the right decision.
As shitty as this makes me of a person, the moment I saw her I was immediately disappointed. I barely recognized her when I saw her; I was fully about to walk past her when she called out my name and grabbed my arm in the terminal. I have no doubt that my look of shock was evident, but I tried to play it off. She looked vaguely like her photos, but was 80 – 90 lbs heavier than I thought she would be and just didn’t have the presence I was expecting.
I was trapped in my own mind as we took a cab back to her apartment downtown and I contemplated what I should do. I liked her personality, but this wasn’t what I was expecting. I made trivial conversation as I tried to break down where I had made the mistake. Had she sent fake photos? Photoshop? MySpace angles? What happened here that I didn’t catch. Was I just so horny for any attention that I missed it?
When we got back to her place we talked for a bit and she offered a few ideas on things to do. I was still trying to decide if I should just book a flight, or a train, or take the bus back home but didn’t want to be more of an asshole than I felt like I already was for being so judgmental. Eventually I agreed to stay, do a walking tour, dinner, all that jazz. I was going to be there for two nights so I needed to make it work.
Before all that, however, she wanted to get laid. So once I agreed to what to do later that evening she sauntered up to me, invaded my personal space, and planted a kiss on me. I could feel time slowing down as she edged closer to me and I remember processing everything slowly. Ultimately, I just let it happen and I kissed her back. I was feeling so awkward and so guilty about how I was rationalizing my behavior and about staying with her in a tiny little one room apartment that I just gave in.
We moved to the bed and she stripped down; I joined her. We continued to make out and it was nice, I missed it, but I was also so torn by the perception of deception that I had and the embarrassment I was feeling that it countered most of the pleasure. I finally leveled with myself that I was being completely absurd. She was still the same smart, clever, interesting person I had talked to online. She was still pretty and she wasn’t unattractive; she just wasn’t my ‘type.’ I just needed to do it. Just needed to commit to the act.
So I moved down her body and immediately began to eat her pussy. Giving oral sex is my fetish and it always turns me on — no matter what — and makes me hard as a rock. If I could spend some time making her cum it would get me in the mood. Well that worked. I licked and fingered her until she came and then I kept going and going and going. I think some part of me hoped that if I never stopped I wouldn’t have to fuck her. That was poor logic — she started to beg me for sex after a while. She was so overjoyed at all of the orgasms she told me she needed to feel my big cock inside her and… fuck it. I just did it.
We fucked for only a few minutes before I came. It had been so long that I had no choice. I filled up my condom and then just kept pumping to make sure I was empty. Perhaps I could use that as an excuse not to have sex again since I had used it all up. Unfortunately, I had already bragged to her about how I could cum multiple times a night, so there was no escaping it.
The rest of the weekend was — overall — quite nice. Boston is an amazing city. Great food, great alcohol, interesting destinations to visit. She and I had sex three more times. That night, laying in bed, I couldn’t help but get hard when she started whispering to me how good my dick was. Cock worship turns me on almost as much eating pussy and she was a master with her words. The next day I woke up to her sucking my cock and what was I to do. I had to fuck her. Finally that night, after trying to convince her I couldn’t cum again, she started to masturbate next to me in bed. As I heard her moan and groan and tell me how she wished I was inside her I got too horny and had to do it again.
When I finally went home I was incredibly disappointed with myself. I took a while to process what I had done, how it felt, and try to figure out why I had just gone with things when I didn’t think it was right. Not sure I ever figured it out, but… at least I got laid.
Source: reddit.com/r/sexystories/comments/n5hkj6/a_trip_to_boston_mf