Pegging a stranger

Occasionally, I browse the "Casual Romance" section of Craigslist. I never find anything worth pursuing, but the fantasy of finding someone and doing something makes me wet.

A couple of weeks ago, I was browsing and came across an ad that I'd never seen before. It was under M4MW and it was a guy in search of a girl to peg him. In return he'd suck the guy's cock and eat the girl's pussy, but he wasn't interested in penetrating either of them.

Intriguing. I've never seen a request for a pegging. It certainly caught my attention. It also didn't include a naked picture, but instead a picture of both his strap-on dicks. His ad included that he had the harness and the toys and would provide them.

I like so much about this ad. A statement of "I want this" and a non-expectation of return penetration. A desire for a couple where the men interacted. Someone prepared with toys so he at least somewhat knew what he was doing. I read the ad aloud to the boyfriend, who responded just as positively as I did. "Email him."

And I did. But I laid our stipulations:
1. I would peg, but that was as far as his/my interaction would go.
2. He could suck my BF's dick and be sucked in return.
3. My BF would eat me out to get me off.
4. It would be in our home on the weekend during the day.
5. I would use my harness but his toys.
When it was over I was all nervous energy. What had I just done? I just invited a third into our sex life!

He replied back agreeing to everything I had laid out. We set a date and time. Then we exchanged vanilla pictures of our faces. Then dick pics. Then the waiting started. I emailed him on a Tuesday but we weren't meeting until Saturday.

Fantasies of the boyfriend sucking dick kept him occupied and horny all week. I was so happy and excited for him. I couldn't wait to see this take place. I knew how much he wanted it and now we would finally share it together.

Friday afternoon, he shaved his whole body, getting all sexy for his hot date.

Saturday morning, I shaved my legs and pussy.

Saturday afternoon, Mr. A arrived.

It was awkward. I suggested we sit and chat for a few minutes just to readdress the boundaries. How much warm-up did he want/need for pegging? What position did he like?

We went to the bedroom. Mr. A went to the bathroom to get ready. The boyfriend was very shy and quiet, but smiling. I was nervous and felt a little out of place in my own home. After all, my part was involved but not the main focus of the event for us.

Mr. A came out of the bathroom fully clothed still. I was standing between them and said, "OK, awkward. Time to get naked everyone..." and just stripped. I was only in a sundress, no bra and panties. I just pulled it off. The men grinned and followed suit.

I pulled on my harness and adjusted it with his dildo of choice. We had agreed he would lie on his back with a pillow under his butt while I pegged him.  I lubed up the toy and asked permission to do the same to him - its only courteous, right? He consented and I wiped a generous amount of lube around his asshole.

He was right, he didn't need a whole lot of warm-up. The toy slid in pretty easily and to aid my efforts, Mr. A pulled his legs up and into the air. After just a few moments he suggested the BF suck his dick, which the boyfriend happily complied after a quick smile at me. I ran a hand through his hair as the BF sucked Mr. A's dick and I slowly fucked away.

Mr. A's dick was about average in length and girth, but this is the first time the BF has ever sucked a dick. I saw him suck hard and pull it into his mouth. I watched his body tense as he fought a gag on this dick. It made me smile to see him working so hard on the other dick, knowing he was loving it. I thought about how much I love to suck my BF's dick.

And soon, Mr. A was jacking off and starting to suck my BF's dick. Mr. A requested that I fuck him harder, so I did, working my hips into him. I held his legs to help give me some help with my rhythm. My BF was distracted by his cock being sucked, so he stopped sucking on Mr. A's for a bit. Mr. A asked for me to pause so he could focus on my BF.

I removed my harness and let the BF eat me out while his dick was being sucked. His attention was obviously elsewhere as it took a while for me to cum. He was moaning into my pussy and flicking his tongue, but he wasn't focusing on his movements at all. I pulled at his hair and told him he was being naughty being so distracted. I kept having to remind him to eat like a good boy. I did orgasm, twice, all the while my BF had his cock sucked by Mr. A.

I sat up and rested my BF's head on my thigh, talking to him quietly. He was on his side, eyes closed, arms around my legs. His legs were wide open, and Mr. A was gagging pretty often on his cock. "You like that, don't you?" He only nodded. "He's a good cocksucker, isn't he? You love having your cock sucked by him!" He moaned into my legs. I ran my fingers through his hair and told him he was a good boy. He was allowed to orgasm into Mr. A's mouth, I know he wanted it. I wanted it to.

And he did.  Mr. A swallowed it and kept my BF's cock in his mouth through the orgasm. Then we both returned our focus to Mr. A. Actually, my BF did. Mr. A wanted his cock sucked more than being pegged, I sat and watched as both voyeur and eye candy. Mr. A was very close to me at this point, and it was not lost on me that his eyes would not stay off my breasts.

I was fine with him looking; I didn't offer him to touch as I didn't want that and he knew there was a boundary there, so he only looked. I told my BF to suck cock... "Yeah, suck that cock you horny boy!" "Don't you just love that cock in your mouth?" "Oh, good boy for choking on that dick!" "Swallow that cock, baby. I want you to choke on it again." "You suck that cock until it cums and you swallow all that cum, baby." "That's my good boy."

Mr. A came shaking in my BF's mouth, who sucked and swallowed and ended with a big smile on his face.

Mr. A got dressed and left fairly quickly. There really wasn't a point in hanging around, I guess.

After he left, I turned to my BF and asked, "Ok, I have to ask -- do I suck better cock?" He smiled at me and rolled his eyes.

"I know you would ask that. And yes, you suck much better cock than him. The only place he wins is that he did it with no teeth at all.... that was awesome."

"Ah... yeah, not sure if I can ever get away from that 100%. I think my mouth's too small for your dick."

"I know, but you still suck better dick."

"Good.... I needed to know."