Tag: Oral

The Business Trip, Night One [MF]

Four nights

Night 1:
My road trip didn’t get off to a great start. In the space of 15 minutes, I got a speeding ticket and two messages from girls I was wanting to play with.

The first girl wanted to wrestle. She was 5’11, only three inches shorter than me. The thought of taking her on was thrilling, because I wouldn’t have an easy win. She also had a pretty face and great tits. But she was also hosting a friend from out of town, and felt guilty being a bad host. Ultimately, she had to say no.

The second girl, was one I found a few weeks earlier, and she was at the time in no shape to be a play partner. She was going through the stages of a break-up and didn’t really notice it when she first started chatting with me. The week before she had been to her first dungeon, and she allowed a Dom to play with her with a shock baton. She really loved it, but she didn’t tell her then-boyfriend about it. I could see the start of a bad pattern, so she got some hard questions from me. Read more »

Summer of Love volume 2 – The Grand Prize (FF) (Amal) (shower) (oral) – Riley Blackstone

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This is the first story IN my upcoming book ”Summer of Love volume 2” let me know what you think

The Grand Prize

Told by Amanda

I can’t believe I won! My boss made the announcement the first of the year. The sales rep who landed the biggest contract in the first half of the year would win a vacation to Caribbean. With a lot of hard work… and a little luck, I won!

I couldn’t wait to tell Emily the news! She and I were about to go on an all expenses trip for four days to the Caribbean! I called Emily as soon as I got home from work.

“Hey Amanda, how was…”

“I won!” I practically screamed at her, cutting her off as soon as she answered. “I won the trip to the Caribbean! I got the biggest client and I got the trip!”

Amanda squealed along with me, the next three minutes of conversation was mostly incoherent from screaming, laughing, and a bit of crying.

“So, when do we leave?” Asked Amanda.

“A week from Sunday.”

“Can you be ready in 20 minutes? We need to go buy new bikinis!” Read more »

The Vacation – part 4 [MF] [cheating] [oral]

Ash stood in the door frame staring into the darkness at me. I could see her but she could barely see me. She was only wearing a pair of skimpy underwear. She gently closed the door and walked towards the bed. I reached my hand down and began to stroke myself as she inches closer and closer. She crawled on the bed and without words began to pull down my shorts and boxer briefs. She grabbed my cock and guides her tongue around the shaft, feeling the growth with each lick.

“Mmm I know you’d be a good boy.”

She swirled her tongue around the head before making it disappear in her mouth. She was emphatic in her approach as she wanted to make sure it was enjoyable. You could tell based on her enthusiasm. In the quiet house, it sounded like a symphony around my cock with all the saliva dripping down her chin and she eagerly shoved it down her throat once more. Her eyes stayed looking up at me to see how I responded. Needless to say, I spent more time with my head back in ecstasy than paying attention. As she bobbed her head up and down, she would grab one of her breasts and would roll the nipple between her fingers making them erect. As she felt me get thicker and harder, knowing I could cum soon, she stopped and slowly stroked me. Read more »

A dare from my older cousin turned a Halloween party into me cheating on my bf [FM]

When I was 19 my cousin (31), who I’m not that close to and only see once in a while, invited me to an early Halloween party being thrown by him and his girlfriend (24). I couldn’t really say no since it was so close to my school and he buys me a lot of wine and liquor to keep in my dorm, so I decided to show up early and leave early because usually his parties are pretty boring and filled with dudes in their mid-30s.

This was a few days before actual Halloween, so I told my BF I would go solo – he lives a few hours away and goes to a different school. He was totally fine with it because he knows my cousin really well and didn’t care.

I dug out my last years costume – a really generic sexy cop kind of outfit that was literally a black tight button up that I buttoned half way, a black cloth skirt, thigh highs with little badges on them and knee high boots. The year before I had a dildo shaped like a nightstick but I couldn’t find it anywhere. I settled on the fake squirt gun I had and put my hair back in a ponytail, it had just gotten to that length after shaving it a while before. Read more »

Sharing My Wife with an Old Pal [MFM]

Years ago, my wife and I discussed having a threesome with another guy. I’m not bi, so I wasn’t interested in anything like that, and I’m not into cuckolding, but it was something I was into, in terms of fucking my wife with another guy. We found a guy, he came over, and it was fun, but my wife thought he was a bit of a dud in the sack, so that was kind of that.

More recently, we’ve been discussing the idea again. My wife is an extremely shy person, but she even went as far to text her high school ex about the possibility. He was very keen, considering they had never done more than oral back then. He seemed a bit flighty though, and was wishy washy throughout a couple of months of infrequent texts about the idea.

I had a friend of mine in mind though, a guy I had worked with once, who I hadn’t seen in a while. Honestly, the perfect kind of friend. We wanted someone we were familiar and comfortable with, or at least I was, but who wasn’t in our life, per se. Read more »

One night with Katherina – Part 5 [M+F][prostitution][teasing][oral]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (*u/lmczpn*) in first person ordering and enjoying a prostitute, Katherina (*u/aurora_w*), who is competent and experienced in the anal arts, but touches on some other kinks along the way.*

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***Katherina:***

As you spur Katherina on, she gets off her left knee and puts her leg under herself in a semi kneeling-crouching position. This raises her head a little higher and gives her a better angle when going down on you and allows her to get your dick a little bit deeper.

She steadies herself on your hip with her left hand. The movement is still methodical and both mouth and hand are in sync. As her head moves down she pulls on your cock with her right hand and it looks like she is trying to stuff her mouth with it. It looks really hot. The strokes from her hand get longer, so long that at some point her lips and hand begin to meet.

You let out a groan and again you see the corners of her mouth turn up in a slight grin. Read more »

One night with Katherina – Part 4 [M+F][prostitution][teasing][oral]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (u/lmczpn) in first person ordering and enjoying a prostitute, Katherina (u/aurora_w), who is competent and experienced in the anal arts, but touches on some other kinks along the way.*

***Katherina:***

Happily Katherina turns around and crawls towards you, getting rid of the denims around her knees in the process. She stops kneeling sitting in her lower calves before you. Her eyes are fixed on what you have to offer and she moves her arms up and her hands glide all the way from your knees (she pushes them slightly apart to make room for her) to your hips and further up your to your navel, then just like a wave on the beach her hands retreat again on the side of your hips but in the process hooking her fingers on the rubber band of your shorts, pulling them down and out from underneath you. Her pull was strong as the movement comes from her upper body pulling back. Your cock springs free. Read more »

One Night with Katherina – Part 1 [M+F][prostitution]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (u/lmczpn) in first person ordering and enjoying a prostitute, Katherina (u/aurora_w), which is competent and experienced in the anal arts, but touches on some other kinks along the way.*

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***Katherina:***

When you called the agency and were asked what you were looking for in your girl of choice you were looking for a nice piece of ass that enjoys anal. The woman on the phone – you could hear her smile through the phone – told you that if you wanted the best piece of ass they had to offer, that would be Katherina, a part Estonian part Norwegian girl that was heavy into all stuff back door. The operator directs you to a website with Katherine’s profile:

She is 24 years old 5 ft 3, has long blonde hair, green eyes and a very fit body

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***Mathis:***

I was immediately smitten by the girl the agency proposed to me. She was beautiful, just like you would expect from an Estonian/Norwegian girl, but what was more important to me, she had an amazing bubble butt I was already daydreaming about. I was envisioning her butt jiggling with every thrust of my cock. My balls slapping against her clit. Read more »

The Vacation – part 3 [MF] [oral] [voyeur]

The day carried on without mentioning the events of the morning. We had breakfast and had our coffee. We then packed the cooler full of beers and headed to the beach.

“It’s going to be a great day. A normal day,” I thought. I begged myself to believe this thought. I had my thick cock down the throat of my best friend’s girlfriend earlier this morning and I enjoyed it. Oh I had enjoyed it. “This won’t be a normal day, will it,” I said to no one.

We got to the beach and I see Ash set her chair and begin to tan. “God, I never realized what great tits she had. Though, I never had to until now.” Ash’s skin bronzed as Jeff and I played some frisbee then took a dip in the ocean to cool off. I came out of the ocean glistening in the summer sun, with my swimsuit suctioned to me, leaving little to the imagination. I walked up to Ash and she lifted her sunglasses like she was a 1950’s movie star and winked. Read more »

My Step Sister [M4F]

This is an account of my experience with the step sister that came into my home for a short period. 

My step sister,

 After my mom remarried I had a new step sister her name was Joni.
We were the same age, both of us were 18 at the time.

One night when our parents were out for the night I was up in my room and had been looking at some porn with my shorts off and stroking my cock.
Joni was down stairs watching tv.

Normally I am able to hear anyone walking around the house however I didn’t hear her come upstairs, my door wasn’t fully closed it was just 
A sliver of a gap.
All of the sudden I was aware of Joni walking past the door, I hurriedly attempted to cover myself but it was to late she had seen what I was doing.

 She walked past into her room and I felt relieved that maybe she didn’t see anything. A few minutes later I saw her sneak up to my door, she was watching me.
I had covered myself at first however when I saw her watching I pretended to not see her and began jerking off slowly giving her a show. Read more »