The beginning

It all started with a very promiscuous girlfriend who was sexy and enjoyed the occasional threesomes with another girl. She was five-feet-nine-inches, with brown hair, beautiful legs, big boobs and pretty thin. She was a more athletic body type. She was twenty-seven and I was twenty-eight. We had been dating for almost two years.

Life was good. We had a great sex life that included watching porn together, role play, and whenever possible another girl.  When we were doing it with a porno on the porn of choice was always a threesome.  Eventually, with enough MMF watching which we both enjoyed, she asked if we could do it with a guy.

I said no at first, but then after some additional porn watching with her, I said yes, under the stipulation that no one we know could know the guy.  I figured it would be near impossible to find a guy that no one knew that was willing to join us.

We had a vacation planned to NYC, and I agreed we could try and find a guy there to join us for a night.

On Friday night of our trip we went out and we thought we had someone interested while at a club. I agreed she could go and dance and try and find someone to take back to our hotel and she let me do my own thing. She made out with a good-looking guy and she even put her hands down his pants while they were grinding. The guy eventually backed off when they realized it was going to be a threesome instead of something one on one. We did have great sex that night and she kept talking about how she wanted another cock to suck on.

The next night my girlfriend invited one of her friend’s ex-boyfriend's friend out, who was one of the few people she knew in the city.  She had met him a long time ago but still had his phone number.  He had no connection to anyone so I thought it was fine.

We all met up at a great bar not too far from the hotel. We were all having a great time getting drunk and taking shots, and I was allowing my girlfriend to facilitate the conversation to our eventual end goal. He was a good-looking guy, thin and not muscular like me but he was two inches taller at around six-feet-three-inches.  After my third trip to the bathroom, I came back to see my girlfriend and him standing by the door. She had already discussed things with the friend and he agreed to come back to the hotel.

When we got back we started drinking more and put some music on. While I was sitting down on the bed she came up and kissed me and eventually got on her knees undid my pants and started giving me a blow job. She did this for about a minute and I was super hard. Then she got up and went and did the same thing to our new friend. After about three minutes she looked back at me and smiles. I take this as an invitation to join.

I walk over and spank her ass. She turns around and starts sucking my dick and then the guy stood up as well and she starts going back and firth between the two. I finally get to see this guy’s cock and it was big. About 7 inches and thick. I’m about 6 1/2 and thick. But he def was a little bigger and had no hair compared to my bush. I remember thinking man that’s a nice-looking dick.

Eventually she stood up and starts making out with this dude. He starts undressing her top and I start taking off her pants and underwear. She is also ripping off this guy’s clothes. Once they are both naked she turns to me to start undressing me. That’s when the other guy drops to his knees and starts eating her out from behind. From the look she gave me I think this guy was mostly eating her ass.

Once I was naked she moved to the bed and got on all fours. I got behind her and started fucking and the other guy got in front and started getting a blow job. I was shockingly super comfortable and turned on. I kept looking at her sucking his dick and smacking her ass and then I realized I was going to bust. I unfortunately never last too long. But I was hoping the beers were going to keep me going longer. I decided to just accept it and go as hard as possible and then I came deep in her pussy. I never bust inside even though she is on the pill, but I knew she couldn’t get upset with me. As soon as I was done I felt weird and went to the bathroom.

I was only gone for two minutes and when I came back she on her back getting it missionary. She had not cummed yet, but I can tell she was close. She was really moaning and grabbing his ass and finally she screamed out I’m going to cum and dug in tight, so he could get as deep as possible and she had a nice long orgasm. I was hoping the guy would cum too, so this could be over but to my surprise he kept going.

They changed positions back to doggy and my girlfriend started sucking my soft dick while getting in it doggy. She would stop every so often and look at me and smile and eventually when I was hard again I laid down on the bed and grabbed my girlfriend to come ride me. She obliged and got on top facing me and then after a minute of her riding me the guy stood up on the bed put his feet right near my shoulders and my girlfriend can now ride me and suck his dick. But now when I look up I have a close view of his balls and ass. He was squatting down a little to make it work and I saw a guy’s ass really for the first time.

I was shocked how hairless he was. Randomly beads of sweat would roll down onto me and I was shockingly turned on. Usually the second time around I last really long. My girlfriend always can make herself cum when on top so at one point she focuses on just riding me while jerking him off she started to tense up and with the sweat, all the moans, and the view on top and above me I cummed with my girlfriend.

I got up again and went to wash off. When I came back they were back in missionary. I was tired and shocked that he kept going. I decided to take a shower thinking it would be over soon.

But when I came back in a towel I stopped and saw my girlfriend was riding his face. I cummed inside twice and this guy is doing that? I decided to just watch. I eventually got back and started rubbing my girlfriend’s breasts and she gave me another look of like wow this is great.

My girlfriend unmounted his face and he sat up and stared at my soft cock. My girlfriend got on top of him and this time I put my feet next to his shoulders and he could see my ass and balls. He started bucking and my girlfriend was really into it. I was half hard and she was barely blowing me, and he took her hand brought it around back. I thought it was to play with his balls. But my girlfriend later told me it was to finger his ass. And that when I was in the shower they 69’ed and he had her put 2 fingers up his ass.

They were going crazy with her on top and her hand reaching back and eventually like me they both cummed at the same time. When my girlfriend got up to go the bathroom I saw the cum leaking out rolling down her leg. he rolled over and started to get changed and when my girlfriend came back he said good bye and left.

My girlfriend saw I was hard and said let me do something for you and don’t stop me. She blew me and fingered me and licked my ass for the first time and I cummed so hard quickly. She smiled, and we talked about the night. She loved how long he lasted but said I fuck better. She also admitted that he rode her face unexpectedly at one point and she licked his ass (something she had never done) and she liked it but stopped him quickly because she was nervous I would get out of the shower.

We recapped everything and even she was surprised that I wasn’t jealous. I said it was normal after all are MFF threesomes. But, I was the one super turned on about how his dick looked and how long he lasted and how smooth his ass looked. I couldn’t admit it, but I was super interested in sucking his dick. And this is when everything started to change. I started going on Craigslist and thought maybe I’d give it a try. But that’s another story.