Author: highcuntry

That time I made my married, overbearing boss squirt all over her hotel bed [MF]

This happened a few years ago at my last job. I was a social worker for a small rural school district, enjoying a few days in the big city at a big annual conference. It is something I look forward to every year. It is an opportunity to get away from the small-town bubble, reconnect with old friends and colleagues and recharge.

This year, however, was different. My district had a brand-new superintendent that was the definition of intense, she wanted to learn all aspects of how schools support students, so she decided to accompany me to this conference to learn more about what it was that I did.

Dr. Newbold was an attractive, dark haired woman in her mid-40s with a husband in his late-50s and two teenage boys at home. She stood about 5’6” with b-cup breasts. Motherhood had softened her figure some, but only some, she was a former Miss Nebraska in her youth, and she cut a fine figure in a pant suit. She was always wearing pant suits. Read more »

I thought I [M] was straight, then I used a young twink [M] as a cum dump [MM]

I had been coming to this college apartment and letting this 20-year-old kid swallow my cock once or twice a week for about a month, and for the last two weeks he had been begging me to fuck him.

Up till this point I had considered myself a straight guy who used men for oral sex during a dry spell (Grindr, plus living near a college campus, made it so easy), but the kid had a cute ass and was submissive in a way that made me want to penetrate him, to use him for my pleasure like he begged me to.

He let me into his apartment wearing only a towel around his waist, which was perfect, when I’m there to fuck, I like to get right to it, no bullshit small talk. He understood this, which was another reason why I kept coming back. My routine was simple: I would come over, we would share a joint, then while I finished the joint he would move his head to my lap and suck my cock like it contained the cure for cancer, I would cum down his throat then be out the door before he got himself back together. It was a perfect arrangement. Read more »

I [M] hooked up with an older [MF] couple in their suburban dream home [MMF]

While visiting Charlotte in the pre-Covid times I matched with an older (than me) couple on a swinger app that said they were looking for a bi guy for some fun with both of them. I was just starting to explore my bisexuality at the time, I still considered myself mostly straight, although I had experimented with local college twinks I had found on Grindr that were eager to worship my well-endowed cock and didn’t ask for reciprocation, I didn’t consider myself attracted to men, rather I was turned on by the situation, their submission to me, and the very skilled blowjobs. I also enjoyed anal play and regularly played with dildos while masturbating.

Anyhow, we talked about what we were looking for and traded photos. She was exactly my type, short with an hourglass figure, a thick, perfectly shaped ass and big tits. He was also attractive, a few inches shorter than me, but muscular, the guy obviously worked out daily and did not skip leg day. He had short cropped hair and some grey was starting to creep in at his temples and chin stubble. They were mostly interested in her being the center of attention, with the possibility of some oral with me and him if it felt right. Honestly they were such a hot couple I would have gone along with whatever they wanted. Read more »