Tag: Swingers

Scotty & His Mom – A Cruise Like No Other – Part 12 [m/s inc]

PREFACE

This story was written at the request of a fellow Redditor who rewards me with pics of his smokin hot mom. I know he’ll enjoy it. I hope you do too! See my profile for previous parts.

Key characters:
Scotty – the son; 25yo; 6 ft; 190 lb; athletic build; blonde hair; hazel eyes; 8-inch cock

Renee – Scotty’s hot curvy, MILF mom; 49yo; 5′ 4”; 160 lb; 36DD-24-38; blonde hair; hazel eyes

Ray – swinger Renee & Scotty meet on cruise. 5′ 10”; 170 lb; dark hair & eyes; 7-inch cock; wealthy.

Stephanie – Ray’s swinger partner and hot THICC MILF; 5′ 3”; 166 lbs; 34DD-24-44; dirty blonde; blue eyes

PART 12

“What did you say?” Scotty asked his mom back in their room. Renee had just started telling her son how Stephanie grilled Renee on how Scotty and Renee had met? Scotty was curious, if not slightly aroused to hear the explanation.

“I told her you were a former BFF’s son.” Renee answered.

“What best friend?” Scotty asked, confused. His mother smirked and rolled her eyes.

“There is no best friend, silly.” She responded. I made it up. Told her you and I grew close.” Read more »

Anal adventures with my man and a 19yr old guy [FMM]

Five or six weeks after the experience we had with a cute redhead, my man (39) and I (36) were out of town when we met this 19yr old college kid at a swingers party. He was a muscular blonde white guy, very handsome, so I asked my man if we could play with him that night, he said yes and took him with us to our hotel room. We got naked and, after the guys kissed and licked almost every inch of my body, I got down on my knees and started to suck their cocks.

I was really horny and loved the way the guys were getting more excited with my blowjobs. The kid grabbed my head and made me swallow his cock all the way to his balls, and his moans turned me on even more. I have to say something in this part of the story, he wasn’t my first young guy, he was actually my third, but he made me experience some new things for the first time. Read more »

How I Turned Myself Into A Perfect Sissy Part III [M23/F26] [Anal]

*I really advice you to read the previous parts first,* [*they are over there*](https://www.reddit.com/r/dirty_boy96/comments/xuwfq0/how_i_turned_myself_into_a_perfect_sissy/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

A few weeks later my transformation was in full swing. I was training my holes, I was wearing panties only, I regularly shaved my body – my roommate was so nice and helped me with the hard to reach parts. My useless dick, my clitty was locked away all the time. I already had lost some weight, regular workouts helped with getting skinny and developing some damn hot curves. And my hair was growing out and I all felt nothing but great.

Also my, or better said our online platforms, because my roommate was a huge part of it too, did great. More and more supporters showed up. More and more men enjoyed watching our content. Or sent me encouraging messages, and yes some money too. It was enough money to think about permanent hair removal, because shaving my whole body nearly every day, was just a very tiresome thing to do. Read more »

Yet I found it Enjoyable [23F] [F/M] [ teasing] [orgasm] [oral]

We host an intern from a nearby institution once per year. typically a junior or senior in college, with the goal of giving them practical work experience in the profession before they graduate. Obviously, it’s a big issue for the intern. Our proprietor enjoys giving back and is an alumnus. Having an additional (unpaid) hand to help with administrative tasks, typing, errands, and other small tasks might be useful for us as well.

Charlie lacked any unique qualities. He was a nice guy and a fantastic student, and I don’t say it in a bad way. But none of this was motivated by him in any way. It’s not that he was simply too attractive or too endearing for me to reject. In really, it was more about me than it was about him.

That summer, I had been divorced for approximately a year. Longer separation doesn’t make it more real, though. At first, it had been difficult. I cried into my pillow a lot of lonely evenings. But as they say, time is a great healer. I began going out with pals and making new male buddies. It was also exhausting. They say there are many fish in the sea, but they fail to mention that there is also a great deal of trash. I kept finding myself on dates with losers, liars, or fantastic guys with whom I just didn’t click. I had a couple casual relationships, but nothing that lasted or was extremely fulfilling. When I met Charlie, I was taking a sabbatical for my own mental health. Read more »

My First Time Going All The Way with Another Girl: And It was FUCKING HOT!

I arrived at Amy’s wearing a barely-there bikini, turquoise. The top lifts my breasts to a position that makes my Bs look like Cs. The bottoms are made of practically nothing, forming a nice little V just above my ass and promptly disappearing. A piece of fabric barely larger than a post-it note covers my nether regions.

I’m sure if I bend over, the boys, and girls can get a little peak if they wish. It’s my go-to swimsuit for parties, especially if I want a little nighttime after-party action. And I usually do. Under my bikini was a short little sundress, hitting me well above mid-thigh, of a slightly darker color. Teal. It was sheer in spots, almost see-through, perfect for going over a swimsuit.

Chris greeted me at the door. He is Amy’s boyfriend, and it was his birthday. I’ve been crushing on Chris ever since he started dating my best friend. He hugged me at the door, pulling me into him, his bare chest pressed against me; insta-turn-on. He is off-limits, he’s my best friend’s boyfriend, but that doesn’t mean that I haven’t fantasized about him. It doesn’t mean that I haven’t stared at my ceiling while fucking myself with a vibrating dildo and climaxing to the thought of him moving in and out of me. Read more »

Scotty & His Mom – A Cruise Like No Other – Part 10 [m/s inc]

PREFACE

This story was written at the request of a fellow Redditor who rewards me with pics of his smokin hot mom. I know he’ll enjoy it. I hope you do too! See my profile for previous parts.

Key characters:
Scotty – the son; 25yo; 6 ft; 190 lb; athletic build; blonde hair; hazel eyes; 8-inch cock

Renee – Scotty’s hot curvy, MILF mom; 49yo; 5′ 4”; 160 lb; 36DD-24-38; blonde hair; hazel eyes

Ray – swinger Renee & Scotty meet on cruise. 5′ 10”; 170 lb; dark hair & eyes; 7-inch cock; wealthy.

Stephanie – Ray’s swinger partner and hot THICC MILF; 5′ 3”; 166 lbs; 34DD-24-44; dirty blonde; blue eyes

PART 10

Fifteen minutes later, Renee and Stephanie were in the dressing room with three bathing suits to try on. Renee had no problem undressing in front of Stephanie as she tried on each suit. The first was a shimmering, canary yellow one-piece with cutouts on either side of the abdomen and a center gold ring holding it all together. The top had built-in push-ups to show off her fantastic tits and the back was a thong style to show off her ass. Renee liked it, but Stephanie wanted to see the others. Read more »

Scotty & His Mom – A Cruise Like No Other – Part 9 [m/s inc]

PREFACE

This story was written at the request of a fellow Redditor who rewards me with pics of his smokin hot mom. I know he’ll enjoy it. I hope you do too! See my profile for previous parts.

Key characters:
Scotty – the son; 25yo; 6 ft; 190 lb; athletic build; blonde hair; hazel eyes; 8-inch cock

Renee – Scotty’s hot curvy, MILF mom; 49yo; 5′ 4”; 160 lb; 36DD-24-38; blonde hair; hazel eyes

Ray – swinger Renee & Scotty meet on cruise. 5′ 10”; 170 lb; dark hair & eyes; 7-inch cock; wealthy.

Stephanie – Ray’s swinger partner and hot THICC MILF; 5′ 3”; 166 lbs; 34DD-24-44; dirty blonde; blue eyes

PART 9

Scotty was standing outside of the cabin room he shared with his mom. He listened through the door but couldn’t hear any sounds of sex coming from behind the door. He knocked softly and waited. He quietly used his passkey to unlock the door and turn the knob. He peeked inside, and found it pitch black and quiet. The bathroom light was on, and he heard the faucet running. His mother was alone. He closed the door and stood outside of it, again. This time, he knocked loudly and yelled. Read more »

Scotty & His Mom – A Cruise Like No Other – Part 8 [m/s inc]

PREFACE

This story was written at the request of a fellow Redditor who rewards me with pics of his smokin hot mom. I know he’ll enjoy it. I hope you do too! See my profile for previous parts.

Key characters:
Scotty – the son; 25yo; 6 ft; 190 lb; athletic build; blonde hair; hazel eyes; 8-inch cock

Renee – Scotty’s hot curvy, MILF mom; 49yo; 5′ 4”; 160 lb; 36DD-24-38; blonde hair; hazel eyes

Ray – swinger Renee & Scotty meet on cruise. 5′ 10”; 170 lb; dark hair & eyes; 7-inch cock; wealthy.

Stephanie – Ray’s swinger partner and hot THICC MILF; 5′ 3”; 166 lbs; 34DD-24-44; dirty blonde; blue eyes

PART 8

“Vea,” Scotty said, remembering the bartender’s first name. Vea seemed to have had several drinks in her. She was with two other women who continued on, leaving her.

“Fancy meeting you here,” Vea said, bowing her head as Scotty rose.

“You look…fantastic.” Scotty said, genuinely, eyeing the slight, landing strip just above Vea’s slit. The dark-skinned, beautiful woman smiled sexily and nodded. Scotty continued. “This is…,” he hesitated in introducing his mother. “Renee.” He simply said. Read more »

[M] meeting couples

I’ve been exploring my bisexual side in new fun ways. I’ve been meeting up with couples on swingers sites for a soft start into bi play. It feels much more relaxing and slow paced to have a woman there to play with alongside the male. Swapping between the two and getting to slowly try new things has been really fun.not sure I want to try male alone quite yet but it’s very fun to play with somebody’s husband whilst they’re masturbating to the sight of us having new experiences

[MF] My Mutual Masturbation Story

I had a good guy friend in college who I became quite close with my freshman year. We bonded over our music passion and love of swing dancing. Josh had a girlfriend back home and I was busy having a bisexual fling with my RA and another affair with my history professor. It was a busy time. My sophomore year though, things slowed down. LeeAnne had started dating someone seriously so I didn’t have a regular fuck buddy. Josh was still dating his girl and to be honest, we were both hard up on a regular basis.

One evening while hanging out in his suite, he was an RA this year, we were having some beers and the conversation turned to sex. We had discussed our sex lives at points but it wasn’t a normal topic for us. He confided in me that he was really struggling to not fuck other women at school but desperately wanted to stay faithful to his longtime love. I confessed that I had not been intimate in quite some time. Excusing myself to the bathroom, I wondered if this conversation would go anywhere. Josh was attractive for sure but honestly, he was definitely in the friend zone for me. Read more »