Her old crush
My wife, Amanda, and I decided we wanted to try a threesome with another guy. It was my idea but she thought it sounded fun. After a few weeks of talking about it we couldn't decide the best way to go about it. Then the perfect way fell into our lap.
We were going to New York and my wife posted about it online. An old friend of hers, Mark, messaged her back and said they lived about an hour away. They were coming into the city for a meeting on one of the days and wanted to know if we would like to meet up for a drink? My wife mentioned it to me but I didn't think much about it. We didn't set specific plans but agreed that sounded fun.
It was a few days before and she mentioned she had spoken to him another time or two. He had suggested a cocktail bar near our hotel. She also said she had to tell me something. She was acting nervous so I was getting worried.
"Honey, I need to confess something to you.". She started. "First I dated Mike. We were just dumb school kids."
"OK, that was a long time ago. I'm ok with that." I said.
She seemed relieved but continued. "We didn't have sex or anything but we made out and stuff. I just didn't want it to come up over drinks and be awkward."
I gave her a kiss and told her it was fine. She seemed satisfied and we went about our day. Something though was bugging me. A little itch in the back of my mind. I realized later it was the "and stuff."
That night in bed I asked my wife about it. She admitted they did more than kiss. They left a dance at school early before his parents were scheduled to pick them up. They walked to the back of the library next door and made out. She admitted he got his hand in her dress and felt her boobs. She even pulled his dick out and gave him a hand job until he came on her. By that point she was pretty worked up and she slid his hand up her dress until he felt her pussy. Even sliding a finger inside. Whether it was a lack of experience or he was distracted since he had already she wasn't sure but he wasn't making any real effort to get her off. She grew frustrated and they went out front to meet his parents. The next day he found out he was moving 40 minutes away. They got in a dumb fight and that was the end of their dating.
She couldn't remember a lot about it but it was one of the first dicks she ever touched. While she told me the story I was getting hard. She leisurely played with my tip as she told me the details. She admitted it was hot and very exciting to her still to this day. She began to rub me and soon I was coming too. As I shot all over her expertly working hand I wondered if this was how good he felt that night. She suggested a toy and I helped her get off while we talked about how good her hand jobs are and how lucky all the boys were who had gotten one growing up.
When we finished I told her how hot that was. She was relieved it didn't bother me and that I was still ok meeting up with him. I asked if he had been flirty and she not really but he had asked if I knew about their past. She had told him we don't keep secrets and she would tell me. That was about it, she said.
As we packed for the trip I suggested she pack a few outfits she felt really sexy in and though she gave me that look she obliged. The second night was the day she planned for us to all meet. We had spent the day walking the Met and though a bit tired I could tell she was excited. She held up 2 outfits. One a casual top with jeans and the other a much more revealing long top over leggings. That one I knew showed off her breasts a lot and the curves of her ass. I suggested that one. She looked at me as if weighing my answer like it was a test. She then nodded to herself and seemed satisfied as she set that outfit out. She then began pulling out her panties and settled on a very thin pair of baby blue silky panties thin enough to leave little line and a matching bra that made her large dd cup breasts look great.
Turns out this place was literally only a block away and we had 2 hours to go. We had agreed to have dinner with him so that was out. As we walked around our hotel we passed an adult theater and porn shop. I jokingly grabbed the door and pointed to the sign about private booths knowing that probably meant glory holes. She gave me a withering look and kept walking. So we settled on a little craft cocktail popup bar next to the restaurant. We were having a great time. The drinks were surprisingly good and she said she loved this place. I think the handsome tattooed English bartender chatting her up didn't hurt.
He plied us with 3 rounds and it was apparent they were stronger than they tasted. By the time we got the text from Mark he was pulling up we were both feeling the buzz. Amanda gave the bartender a big smile and said we would be back soon. He told us his schedule and I was wondering if my fantasy might happen in NY.
When Mark walked in he gave me a friendly handshake and her a hug. He was a clean cut looking guy about our age and he looked like he kept in decent shape. As we chatted about all the typical things my wife was definitely showing the effects of multiple cocktails on an empty stomach. He didn't seem to mind and as soon as her drink was empty flagged the waiter for another round.
As we began to run out of basic questions like work family and travel we hit some awkward silences. He asked what we had done earlier in the day and my wife told him about the Met and the cocktail bar next door. Then slipped about the hot English Bartender.
"I knew it!" I laughed back.
Mark joked that she might be in trouble with me later and she said "No, he probably likes it." She then excused herself to the restroom.
When we were alone he asked if she was drunk and I said typsy for sure lol. Then he asked what she meant about me liking it. I'm not sure why I told him but apparently I was feeling the drink as much as her. I admitted we had thought about a threesome. He didn't seem offended but did seem thoughtful. I assured him that wasn't why we met up... for some reason we both paused then we both burst out laughing. I'm still not sure what was funny except at that moment, I wondered if he was the one. He seemed to have the same thought and when we saw the look on each other's faces it was so awkward we had to laugh.
My wife came back unsure what we were laughing about and when neither could explain it she simply shrugged and ordered another drink. It was his turn to excuse himself for the bathroom. While he was gone I told her he asked what she meant. She felt bad she slipped and said anything to him but I said maybe it's a good thing. You never finished with him. Aren't you curious what his dick would be like? She said she hadn't thought of him for years until he messaged and never planned for that tonight. I told her the choice was hers. He seemed interested and I was fine with it. She could have him tonight if she wanted. My stomach was in knots but I left it there. Ball was in her court now.
We ordered dinner and the conversation came easier as we talked. The sexual tension seemed to grow though. Was it in my head or did everyone feel it? His eyes definitely seemed to wander over her breasts a lot. She had let her shirt slip pretty low and didn't seem to mind. Sex kept coming up and my dick was half hard all night. 7 drinks in and I was buzzing. I swayed a little in the bathroom and my mind was unfocused. Was she going to do it? Was she thinking about it now? Talking to him about it?
The answer seemed clear when I got back and she said we were leaving. He was going to walk to the hotel with us. I said great and helped her in her coat. We both grabbed an arm and led her out into the warm night. As we passed the porn shop she pulled us to it.
We both asked why and she looked at me and said "Condoms." Then turned to him and said "unless you have any?"