I decided to go visit some friends in New York City just after Christmas one year. It was going to be a whirlwind tour staying with a different person for a night for five nights. Some of these people I knew through family, or from high school, and two of them I had met years before on HotOrNot — which was kind of an early version of Tinder.
All of the friends I was hanging out with were platonic friends. Sure, one of the girls from high school had a crush on me — but it wasn’t reciprocated — and the two girl from HotOrNot had been genuinely good friends to me for so long that I wasn’t trying to push my luck into a hookup. I just liked hanging out with them even if they were both beautiful.
Well, technically, I did sort of try to hook up with each of them once several years prior but I blew it both times. The first I just didn’t make a move on at all. She came to my town, got a hotel, we went out and had a great time, but when it came time to being the man… I just didn’t do it. Thanked her for the great evening and drove home at 2 am leaving both of us unfulfilled. I got into a car accident that night too… I was so distracted thinking about how I fucked up that I hit a parking column.
The other one, I’ll call her Veronica, had also come to visit me one weekend and gotten a hotel. I tried to take her to a show, but got lost on the way. I tried to take her to dinner, but the place was booked. I tried to take her dancing, but she didn’t want to do it after the full day of not making it to the places I tried to take her. When we went back to her hotel room I just felt so defeated that I never even thought about making a move. Again, they became great friends after that, so I’ll never complain about fucking that up. Especially, as it finally came around that I had a second chance with Veronica during this post-holiday visit.
She was the last person I was visiting and I was staying with her on a Sunday night. Let me tell you a little about Veronica. She is an incredible person. 5’10”, Italian, brunette, dark eyes, tan skin, great body, and an amazing personality. MBA, whip smart, successful, talented in 10 different ways, great sense of humor. I adored her and, for some reason, she adored me in kind.
I had been visiting Veronica or vice versa once a year — maybe skipping a year occasionally — for the past nine years. I had met her friends and family multiple times and it wasn’t uncommon for me to show up at her birthday parties or graduations as a surprise. So her people knew me, and that night we were going to hang out with some of her people. We had a good time at a baby shower, then went to dinner with some other friends, then she and I stopped at a bar near her place to have drinks and catch up 1:1.
I had recently ended things with a long term FWB and had not had sex in about three months while I was waiting to hear from a girl that was trying to decide if she wanted to be with me or not. ***Feel free to read the story I posted yesterday for more details, this story takes place in a narrow window of time during that period.*** So at the bar that night I unloaded to Veronica about my situation, my past, my feelings, and my overall crazy horniness built up after not having sex for so long after having it 5 – 15 times a week consistently for years.
Veronica, wisdom just emanating from her all the time, laid down the law and told me how incredibly dumb I was. She helped guide me through my BS and, when she was done, unloaded all her baggage on me as well. We were drinking hard liquor; being deeply, deeply honest with each other; and it was exactly what I needed. At one point, after talking about the breakup she had just gone through — having been cheated on by her long time guy — she confessed she was feeling down about herself and wasn’t sure if she was even that attractive. I assured her, immediately, that she was one of the most attractive people that I had ever met — which was true. I explained that it was probably a matter of people not talking to her because she was too attractive to be considered approachable.
“If you think so, why didn’t you ever make a move on me?” She asked bluntly.
“I always wanted to, but you are too gorgeous, too sexy, too incredible. I didn’t want to fuck it up.” I confessed.
“You don’t like me.” She shook off my admission casually, “You told me years ago that you would never date someone with brown eyes.”
“Oh my god.” I was gob-smacked, “I said that when I was like… 19. On AIM. Because I was a dumb kid. I didn’t mean that. I’ve dated lots of people with brown eyes.”
“Bullshit. I never thought you were attracted to me because of my eyes.” She was being completely genuine.
“No, no, no. I’ve always been incredibly attracted to you. You are perfect.”
“I don’t believe you.” She looked me dead in the eye and wet her lips. I finally had the courage to do something about it and I moved in to kiss her. She kissed me back and then there we were, making out at the bar like the two lovesick fools we were.
We took a cab back to her place and made out the entire way there, the entire way up the steps, and the entire way back to her bedroom. We stripped each other naked along the way. In a flash we were in the improbable position of being friends who thought that we weren’t attracted to one another when we had been the entire time. She was a sight to behold. Long legs, full breasts, cleanly shaved pussy. She was happy with what she saw in me as well. I was in the best shape of my life, my thick cock was rock hard, and I had a pent up lust that she was going to bear the entire benefit of.
She reached out her hand and wrapped it around my cock and guided it to her mouth as she sat on her bed. She licked all around the head until it was nice and wet then licked either side of the length of my shaft. Finally she spit on it and rubbed the wetness in with her hand before wrapping her lips around me. She pushed her head down as far as it would go as I began to hit the back of her throat and she gagged just a little. She looked up at me with her big doe eyes and I was struck by the tragedy of having ever said something so dumb about not dating brown eyed girls.
She played with her pussy as she sucked my cock and it was turning me on like crazy. I wanted to feel her on me; I wanted to be inside her. I told her as much and she lay back on the bed immediately. I got in bed with her and we kissed long, deep, passionate kisses. I took one of her dark nipples into my mouth and played with it as I slipped two fingers into her. She was incredibly wet and was obviously just as turned on as I was. Normally, I would have taken the time to go down on her before fucking her, but I was impatient and needed it right away.
I moved her long legs onto my shoulders, took the condom that she handed me and slipped it on, then dove right in. Her pussy swallowed my cock whole and it felt like velvet. She gasped and moaned and told me that she always imagined that had a big cock. The whole time we fucked she confessed all the things she liked about me. I did the same in return and shared with her all of the times I had jerked off thinking about her, wishing we were doing what we were finally doing now. We were both so wildly horny that each of us came very quickly. We cuddled in her bed afterward and laughed at how stupid it was that it took us this long to figure it out.
After some water, a bathroom break, and a little time to sober up we started things again. This time more slowly and deliberately. We had sex once more after that, and then made love once when we woke up aroused at 4 or 5 am. It was a deeply intense session where I think we both used one another to express something special with each other because we had such a close level of trust and respect in that moment. It was unexpected, wonderful, and very healing.
The next morning I kissed her goodbye then headed home. I thought about her the entire time and was thinking about what it might mean to give up my life as it currently was to move to New York and give being with her a shot. Unfortunately, I never pursued it. That next night the girl I had been waiting to hear from — but had ghosted me after two nights of love making and a lot of promises — finally called me and told me she was moving home and wanted to give it a shot with me after all. I forgot all about Veronica and our special connection for a few months until things blew up in my face and I ended things with the other woman once and for all.
I think it all worked out though. I am still incredibly good friends with Veronica. My wife adores her too. My wife doesn’t know about this story or the night of passionate sex that Veronica and I had — but I don’t think she would mind. In fact, my wife thinks Veronica is just as interesting and attractive as I do; perhaps one day we’ll invite her to join us as a couple.
Source: reddit.com/r/gonewildstories/comments/n4mtdp/i_had_sex_with_one_of_my_best_friends_after
God damn that is somehow both hot and wholesome!