[MFM] My First Cuckoldress

The first time I fucked a cuckoldress was a few years ago, back in Las Vegas. On my way into town, my local booty call wasn’t returning messages. We had a bit of a falling out, so I was starting to accept that she wasn’t going to be an option. So I turned to the dark realm of Craigslist.

I was trying to post a M4F ad, but hookers liked to knock those down to force men to browse their F4Ms. So I placed a M4MF, posting a pic of my cock cumming, and noting that I wanted to fuck a girl in front of her boyfriend.

This couple was amazing by the size of my cumshot, so we met in the lobby of the hotel I was staying at. He was tall and lanky, she was short and fit, wearing a tight black dress and sneakers.

There were these tiny couches – I sat next to her, forcing the guy to sit opposite and watch me flirt and chat with her. We talked a bit about our travel plans and some other naughtier topics. Occasionally I let my hand brush against her knee or thigh. She never flinched, and he grinned every time.

Reconnecting with Nikki [MF]

Nikki texted me out of the blue. “Hey,” was all it said. A couple months prior we went out a couple times, had sex, and she ghosted me. I liked her more than I should have, and I texted her back a few hours later. That night, we met for drinks and made out. Most importantly, we made plans to do dinner at my place in a couple days.

Nikki’s hair was dark brown with reddish highlights, and it fell below her shoulders. Other descriptors: 24 years old, 5’-7” tall, hazel eyes, and pale skin. She had a stud in her nose and several piercings in each ear. She took care of herself but also had curves – a combination I find very sexy. She had a punk/hipster vibe that I adore.

I’m Nikki’s opposite. My name’s Dylan. I work at an engineering firm and I fit the engineer stereotype to a T; I’m mild mannered, reserved, and average looking. I’m affable, but I lack charm. Here are my physicals: 5’-10” tall, 170 lbs, and hazel eyes. I was 27 years old at the time. I had bushy dark brown hair. My nose is large. I had a full beard and mustache that I kept nicely trimmed. I hit the gym regularly. I’m not buff, but I have definition. I have full but not super thick body hair, and thankfully no back or butt hair. Well ok there’s a patch between my shoulders and another at my lower back in the interest of full disclosure. My skin is pale.

[M]y ex-wi[F]e’s nanny

My wife and I divorced a few years ago. It was about as amicable as it could be. We have 2 kids under the age of 8. She has custody most of the time. She has a nanny to take care of the kids after school and during parts of school breaks. She is 23 and getting a degree in early childhood development at a nearby university.

I had the kids for Thanksgiving break. I decided to take them on a week long trip. We went to Disney World for a few days and then to an island in the Caribbean.

I wanted to be able to enjoy the vacation a bit myself so I asked if the nanny might be interested in coming to help out a bit. My wife was fine with it. I discussed it with the nanny and we came to terms on payment. I asked her to work roughly half time. She was going to take care of /assist me with the kids during 4 days and was going to watch them at night for the 4 other nights.

My once time shy ex girlfriend is now my personal whore [MF]

A few months ago I told you how I fucked my long time ex girlfriend again. Since that night she has been chasing me but I had no real intention to reply her messages.

Walking back home the other night I met her. She was having a drink at a bar just near by my building. I noticed her when she called my name and asked me to join her and her group of friends.

They were talking about films, she introduced me as one of her best friend (ahaha). During the conversation she kept staring at me and I could notice her nipples pointing under her tee shirt as she was wearing no bra (I could not tell whether it was because of the cold or because of my presence… or both…). I must tell how beautiful are her small tits and I will always remember them bouncing during our fucking sessions.

[f]ucked a singer in the [m]usic studio (one crossed off the bucket list! ;)

For the longest time, I had wanted to have sex with a girl in my music studio. It was one of my top 5 fantasies on my ‘sex fantasies bucket list’, and this story is a retelling of how one of them is now decisively crossed off.

I will refer to girl as Jenny.

Jenny the singer and I met though a mutual musician friend. We were all keen trying to create something. Having exchanged a few messages, she seemed to prefer the idea of brainstorming in the studio with just myself first before including the mutual friend musician. The potential that this might imply that she was interested in exploring something sexual was already good enough material for copious masturbation. We eventually agreed on a day to meet.

As soon as she got in my car I became very intrigued. Jenny’s about 5’7″, a good healthy weight, blonde, and has a very positive, ‘bubbly’ attitude. She looked a bit better in person than in her social media photos. The closest porn star lookalike that I’ve found is Madelyn Monroe.

Root Canal Relief (l o n g)

One afternoon, I woke up sharply from an unplanned nap to a searing pain in my back molar. The hot, focused agony was unique in its strength. I’ve certainly felt sensitivity in my teeth before (a childhood spent loving sweets taught me all about that), but this was clearly different.

I rushed to the bathroom and downed 4 Extra Strength Bayer, the cool tap water causing a fresh sting on the way. I breathed sharply through clenched teeth. This was a nightmarish pain that I needed immediate care for. I did a long, thorough rinse with Listerine and that helped a bit, but it was evident I needed medical attention.

I pulled out my phone and ran a search for nearby dentists. Through some miraculous stroke of fortune, I had only recently acquired dental insurance through my job. Despite the pain I was feeling, this revelation caused me a needed emotional boost.

The search had found a few well-rated dentists nearby, but in my post-nap, ache-plagued disorientation I had failed to notice that it was 5:30. Nearly all of these were closed. One had hours until 6:30, so I grabbed my keys and rushed out the door.

Hooked up with my Best friends Fiancée on our couples vacation [MF]

Hello, My girlfriend and I rented a lake house with one of my old friends and his fiancée. The house had two bedrooms that shared a master shower/bathroom, I woke up early one morning and took a shower, and forgot to lock both doors…
When I was getting out of the shower my friends fiancée walked in wearing only a towel. I covered up and awkwardly apologised but she just stood there with a menacing look on her face. She dropped her towel…She’s about 5’4″ and slightly in the chubby side, but she has big beautiful boobs, beyond DD but still somehow perky.
I pulled off my towel and was starting to get hard, she walked closer to me and leaned her knees on the edge of the bathtub, she took my now throbbing hard cock and slowly moved it between her enormous cleavage.
We titfucked for a few incredible minutes then she gave me an incredible blowjob, I struggled to remain silent while finishing in her mouth.
Since then we’ve never done anything, and now we’re are both married to the same significant others from the trip. We’ve giggled about it a few times since, and she’s sent me a couple nude pics over the years, but other than that we’ve gone back to loyal spouses..feels good to get this off my chest.

[MF] The drum room

My first story, so bear with me. English is also not my primary language, so sorry for the spelling errors.

Some time ago, when I was a student I had a strange experience with a girl at the same school. It all started after a long and hard party at the student pub, I walked in on a friend of mine and a girl that I hardly new before around the corner from pub. He had a very nice girlfriend but I could see that he was about do to something stupid with this other girl. So I went up to them and asked them where the afterparty was, teasing them about what they were about to do, saying that I would never even kiss on the first date, and surely not doing enything more. I continued talking to them and managed to get them with me to the place I was going. The girl was a bit dissapointet, but as a twist she hang on to me instead of my friend, talking flirting, teasing. Nothing more happened that night.

[mf] a nice surprise.

My wife has been trying to wake me up with sex for a wile now. For the most part I wake up the second she touches my cock. This morning she succeeded. We have been long term baby sitting and have been very tired because of it, we also have not had sex for 2 weeks in fear that the kids would hear us or even walk in on us. The kids went home yesterday morning and I started a new job as soon as I got home we ate dinner and went directly to sleep. I guess I was out because this morning I woke up hard as a rock with her lips wrapped around my cock. I was kind in a daze when I first woke up and just lay there watching enjoy the waves of pleasure of possibly the best blowjob I have ever had. It wasn’t very long after waking I was ready to cum in her mouth. She swallows ass she always does but this time I can see the added excitement on her face because she was able to finally wake me up and get me off. I’m still hard but tell her to roll over that it’s her turn. She responds with a sinister grin putting her hands on my shoulders and pushing me back into the bed. As she climbs on top of me she says in a stern but playful voice “I need that hard cock deep inside me and you worked hard enough yesterday” she reaches in between her legs grabbing my cock to guide it into her pussy and it slips in with ease she is so wet. She looks me in the eyes and starts rocking forward and back, lifting her butt up and down. Her breathing start to get heavier and faster she whispers “god you feel amazing” as she starts to pick up speed. I feel her pussy start to get tighter around my cock as she tilts her head back and starts to moan, then her legs start to quiver. I put my hands on her hips and pull her down further onto my cock, her breathing is now out of control as I start to feel the moisture from her tight wet pussy run down by leg. She tells me she’s cumming half in a moan half in a scream as her entire body starts to shake. Hearing this makes me instantly cum deep inside her. She collapses onto my chest whispers I love you, and that’s where she stayed until her breathing calmed and she fell back to sleep.