First cock and more

Sheridan and I met in an online dating site and hit it off immediately. These meetings usually result in at least a few weeks of messaging before trusting enough to exchange phone numbers. We did that the first night. We're both retired and single but live about 400 miles apart - a hurdle we agree we can figure a way around eventually.

One of the things that attracted me to Sheridan is her confidence and openness about sex. She told me early on that she loves giving oral sex, and promised that if we got together she'd give me up to 5 bjs a day! We've met that goal on several occasions as I write this. In fact, she's beneath the table enjoying my cock right now, making it a bit challenging to focus on my writing.

One activity she did exclude is anal. She told me the first time we met face to face (with all mutual intentions of having sex) that she doesn't do anal. "It hurts", she said. I replied that it needn't if done properly but also said I would always respect all her wishes. Subject closed, I thought.

A few weeks back we were sipping chilled glasses of Pinot Grigio in bed after a rousing session. "Have you ever had a threesome?" she asked.

"Yes, twice", I replied.

"Two women and you?"

"Yes, both times but they were different women. About 20 years ago I was asked to join a married couple but I declined," I told her.

"Why?"

"I wasn't as self-confident back then."

"Any regrets?"

"I regret that I didn't have the confidence to discuss it in detail. I never did find out just who they wanted to do what to whom. He did tell me up front that it was her idea and fantasy and he was fine with letting her have it. And I was a bit afraid that they might overpower me and force me to do something I didn't want to."

"What didn't you want to do?", Sheridan asked.

"At the time I didn't want to have any contact with another guy", I replied.

"At that time? Does that mean you're okay with the idea now?"

"Well, I don't know for sure but I will share something I've never told anyone. You know I love your blowjobs, right? Well, I sometimes wonder what it feels like to have a cock in your mouth. And I'd like to see if guys suck different from gals. Seems like they might since they know exactly how it feels best. I just don't think I would ever act on it." Sheridan moaned softly as she heard this.

"OMG, Tony! It would be sooooo hot to see you sucking some guy's dick! You have to do that for me!"

"I don't think so, Sheridan, but it's interesting that you nearly came just hearing me say it!"

"I'll make you a deal, T. If you do that and let me watch, I'll let you have my ass!"

My cock, which usually takes a while to recover after cumming (symptom of my age) immediately stood at attention when she said that. "Sher, are you serious? You've always insisted that the back door is and will remain one-way only. Now you're willing to let me take that virginity?"

"Yes, but only if you do a guy. And it has to be all the way...he cums in your mouth, you show me the load, and then you swallow it. And I get to take pictures and a video!"

"I need to think about this. I'm not even sure how I'd find a guy."

"Oh I'm certain there are tons of guys more than willing to loan you their dick in exchange for a blowjob! And just to sweeten the pot, if you'll grab the lube I'll turn over and you can finger my ass. No entry, yet, but you can play there." And so we did, me playing with her anus for the first time.

Over the next few weeks I eased Sheridan into the world of anal penetration. It's important to work your way up in size when dealing with an anal virgin. Once she'd gotten comfortable with a single finger, I added a second, then a third, and finally all four. When the middle knuckles are inserted the circumference approximates that of my cock.

Three weeks later we're in a hotel room waiting for him to arrive. I had opened an account on a well-known hook-up site for gays and bis and, as Sheridan predicted there was no shortage of volunteers. I put in my profile my criteria: clean, circumcised, about my size, one-time only, he has to do me first, and allow pics and video although Sher would make sure his face was not in them. He would get to see them before leaving. We'd keep the room for the rest of the night so Sher could make good on her part of the deal.

I was indulging in a little liquid courage, but only one so as not to impact my ability to perform. I was half done when the knock came on the door. I let him in and found him to be just as he'd presented online. I poured him a scotch and the three of us chatted for about 15 minutes to get over the awkwardness that I felt (he seemed relaxed from the start).

Once we'd both finished our drinks we got undressed. I lay on the bed and he went down on me. I'd wanted him to go first so that I could recover while doing him and be ready for Sheridan afterwards. He did feel different than the women I've had do that but I can't honestly say it's because he's a guy. Might just have been that he's pretty damn good at cocksucking! He sensed when I got close and eased back, drawing things out as long as he could and as long as I could stand it. When I finally came it was, as I had warned him, a very modest volume. After about 45 men's volume begins to decline.

After a few minutes rest and deep breathing it was my turn. At about 50 he claimed to retain pretty much all the volume he'd ever had. So I expected to be in for a challenge. I lay across the bed, resting my head on his abs then reached out and licked the head of his cock. It jerked in anticipation as I moved down and engulfed it. I started by taking it as deep in my mouth as I could and then bobbed up and down. At the same time, I used my hand to stroke the base of his shaft. That was also a safety measure, since I know that most men instinctively thrust in a deeply as possible when they cum and I didn't want his cock to choke me.

All the while Sheridan was taking pictures with my phone and video with hers. Though I lost all track of time, a viewing of the video afterwards showed that I sucked his cock for about 12 minutes, as I too pulled back when I sensed him getting close. But eventually he couldn't deny his urges and he shot a large load into my mouth. It was one of those times when, as he filled my mouth air escaped from my lips around his cock, but I managed to retain nearly all his cum.

The texture didn't bother me as I've tasted my own cum more than once. I always figured it was only fair if I expected women to take it and swallow so I tried it every six months or so. His taste was different, most likely due to dietary factors. More salty than mine (but I consume very little salt) and with an undertone of flavor I couldn't identify.

Pulling off my first cock, I turned to Sher, opened my mouth, and stuck my tongue out to show her. She snapped a couple of pics and took video then moved in to kiss me deeply. I shared some with her then swallowed and opened again to show it gone. Then I turned to our volunteer and said "Thank you, for both!" He smiled, thanked us, and after reviewing the video and pics, got dressed and left.

"How was it?" she asked.

"Interesting. I have a much better understanding of what it is like for you. But I'll never love it the way you do!" I smiled. "Did you like watching?"

"Watching him blow you made me a little jealous. Watching you suck him made me cum. Four times, hands-free". Now it was her turn to smile - and to make good on her part of our deal.