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My First Time
I put an ad up in M4W on a free classified website a lot of years back after Fran and I divorced. I had no expectations. I was buzzed one night and thought what the hell and wrote an articulate, pretty funny ad in which I really just wanted to have some company. Out of the responses I received, one really caught my eye. It was from a guy who told me right away he wasn't a woman but he and his long time girlfriend have been searching for someone like me. It was a long, well thought out an email telling me all about them and their relationship and how they would like to find another person to add to their sex life. It was intriguing and very complimentary so I responded.
There was NOTHING in the email to suggest that he was submissive at all or looking to find someone more to her alpha liking. I described myself as being real laid back but masculine and assertive. He shared my responses and pictures with his girlfriend and they responded with pics of her. She was absolutely stunning. A total knockout. As hilarious as their emails were I was hoping for like a 6 or 7 but she was a 9. Very small and petite with a gorgeous frame on her. They gave me her number and we texted back and forth for a couple of days before agreeing to dinner. I was astonished to see that she was far more attractive in person than in her pictures.
I got to thinking when I saw her that she was more than likely out of my league but I was going to give it my best shot anyway. We drank, conversed, and ate for a couple of hours and headed out. I received several indications that she was into me but I was uncomfortable making any moves since this was essentially a feeling each other out date. We gave each other a hug and she said she had to call her boyfriend and tell him all about me. He emailed me and said they both thought I was awesome and set up another single date. I again thought I was on some sort of interview so I was on my best behavior.
We saw a movie and ate dinner at a nice restaurant. I never tried kissing her or putting an arm around her all night because I didn't want to ruin my chances. At the end of the night as I put her in her cab she leaned in for a kiss that I wasn't expecting at all and I completely botched it. 15 minutes later she called and said, that she would have let me take her home that night. We were both pretty buzzed after cocktails and she was coming on pretty strong. At one point she asked how big I was. Most guys LOVE to fucking lie about their dick size. I'm not one of them.
I figure if anything you undershoot it and then when it pops out of the underwear they are pleasantly surprised. Besides, 8.5 inches is nothing to scoff at when compared to most dudes. I told her and said it's the equivalent to when most guys probably tell her they are 9 or 10. She asked about my stamina and I told her I had no issues. She then requested a picture, which I've never been asked for in life of my dick, but I thought fuck it and sent it to her. She was pleasantly surprised.
The boyfriend later emailed me that I misunderstood what their limitations were. I was free to go as far as with her as I wanted when he wasn't around and if it helped I could pretend he doesn't even exist. He then called me on the phone and we laughed about how bad I botched the 2nd date and how I was going to have to redeem myself next time. They invited me over to see both of them last weekend. He cooked a VERY nice meal, we shared some mixed drinks and sat down to watch a comedy.
He jokingly pulled out some porn and said, "We could always watch this?" And we just laughed and settled on a lighthearted comedy. 15 minutes in or so she came and sat next to me and leaned in for a kiss. We had a long passionate kiss while he rubbed her all over and in between her thighs and she whispered to him to go down on her. He said "No he gets to first" and she kicked a leg up over his head and pushed him down. It was pretty hot. As he went down on her we continued to make out and she rubbed my dick through my boxers. Throughout this, I drank all 3 of our drinks.
Every time I ran out he'd hand me one of theirs until they were all gone. He offered to go make another for me and left the room. She got between my legs and asked what I wanted. I picked her up and took her in the bedroom. I laid her down and went down on her for 5-10 minutes and when he came in he just stood quietly in the corner, which I felt odd since I'd be trying to get a blowjob at least. She got up and went between my legs and gave me some AMAZING deep throat and put her ass in the air and called him over. Both made comments about how much bigger I was.
He was probably rocking 5 inches hard. He got behind her and ate her out while she blew me. She eventually climbed on top of me and rode me and moved his face to her ass. At one point my dick slipped out during her multiple orgasms and he quickly put it back in. Later we did reverse cowgirl while he licked her clit. Again my dick popped out (twice) during orgasms and he slid it back in. I've NEVER had male to male contact so this was new to me but the moment was so intense I just went with it. It was pretty amazing. Eventually, I was getting ready to cum and he told me she didn't want it inside that she loves it on her so I pulled out and shot it all over her, especially in her face.
She had that glossy-eyed, content slutty face that is just magical to see. He immediately dove in and fucked her and kissed her cum covered face and then shot another load on her. I was asked to sleep in their bed and after we all fell asleep he slipped out and went to another room. She woke me up with more amazing head and we had sex again. The best part wasn't how hot she was or how I became the alpha male in the room. The coolest part was how intimate and natural it all was.
There was NEVER any awkwardness. They truly loved each other and were so into it the whole time and I loved being a part of it. She would lock eyes with him as I was fucking her and smiled and say naughty things like "Is this what you hoped for baby? Do you like seeing his big dick in me?" At one point she struggled to take me all the way in missionary and he was encouraging her to take it all. She looked at him and said "really? You want me to take it all? No matter what?" And he kissed her and said yes no matter what. I thrust it deep and she had an orgasm on the spot. Nothing was ever been mentioned about cuckolding but that's obviously what has happened and will continue to happen. I'm not into the humiliation aspect of stuff yet but he has made several comments in front of us about how much bigger and longer-lasting I am. I'm enjoying the ride...