Category: sexystories

[MF] [MFM] Anonymous Sex at a Beachside Resort!

Main kinks: Free use, Anonymous Sex, age gaps

It was my second day at a beautiful beachside Caribbean resort. I needed a break from the high powered demanding job that often kept me completely occupied and this resort seemed to be the perfect place.

I decided to get out of the sun for a bit and walk around the buildings, and If I’m being honest I was hoping to satisfy a bit of my vouyeristic fantasies with a view through the sliding glass doors of the first floor rooms. But when I rounded the corner of the quietest area in the resort what I saw shocked me: A big white ass protruding from one of those glass doors, with the curtains drawn at the waist so I couldn’t see anything inside. She seemed to be laying on her stomach, her legs hanging off the end of an ottoman pushed halfway out the sliding glass door. I had to stop and collect myself, as almost instantly a tent formed in my swim trunks. Looking around there didn’t seem to be anyone else so I quietly approached the patio. Read more »

Like Mother, Like Daughter – The First Collection – Free on Smashwords! [MFF]

Be sure to pick up your free copy during Smashword’s Sale.

Link to download in comments.

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Teaser below:

**Part One**

**The Deal**

It was a beautiful summer day in southern Sweden. The sun shone down from a clear blue sky while I was driving along the fields in my BMW M6 Cab. I had only owned it for a couple of weeks and I was heading from my summer house outside of Kivik into work in Lund. When I was closing in on Loberod I remembered that there was a little Thai food wagon there that served an excellent fried rice. I drove into the small town that most people just passed through if they even knew that it existed. After a couple of hundred yards I saw the food wagon. It stood just where it used to, it must have been two years since I last ate there. I pulled up the car to the curb and stepped out. Two wooden tables with benches were placed just next to the wagon and two teenage girls sat there drinking Coke.

”Nice car”, said the first girl. Read more »

The Doctor – [M/F] Pt 3 of the story of a pregnant woman’s rather unconventional examination.

“I’m … I’m sorry Doctor … I didn’t mean to … I’m so sorry … please, please – I really would like to have the Anal test done today. Please?” she asked in her most demure and apologetic tone. Doctor Hendricks glanced over at her, his eyes surveying her whole body like a scanner. After a moment he gave a low hum and stood up.

“OK. We should do the anal tests today, I suppose. If you’re sure you’re happy to proceed” he asked, looking directly at Ana. In response she nodded avidly and smiled “Oh yes, yes please … yes the anal tests are so important aren’t they” she said in mild encouragement.

Doctor Hendricks nodded in agreement but didn’t speak. Grabbing Ana’s ankles he pushed her legs back until her ass popped up and her ass hole was clearly visible. “Did you clean it out, like I told you?” he asked, looking in her eyes. Ana smiled “Yes, just as you asked Doctor. Washed it out, and made sure to empty my bowels” she beamed, proud of herself for following his orders. Read more »

The Doctor – [M/F] Pt 2 of the story of a pregnant woman’s rather unconventional examination.

It was exactly a week later when Ana again waddled into Doctor Hendricks’s office and sat down with a smile and a slight grimace. “Everything OK Ana? You look nervous. There really is no need to be you know” said the Doctor, ushering Ana to a seat.

“I’m … I’m sorry Doctor, I’ve never had an Anal examination before.” She said smiling winsomely. Doctor Hendricks took her hand and patted it. “There, there – it will be OK. You will be OK. It’s best to be safe, isn’t it? Best to know that your body is coping well with the pregnancy?”

Ana nodded and a fuller smile drifted across her face. Doctor Hendricks coughed and looked at his computer screen “Just a few questions first” he added tapping his keyboard. “Did you manage to get your daily shot of cum, like I recommended” he asked directly.

Ana nodded, licking her lips absently as she remembered them. She recalled every spurt, every last tendril of cum that she licked off the many cocks she had sucked that week. “I … I went to the homeless shelter as you suggested, and I … I spoke with the warden there and gave him your regards.” Read more »

While you were out I had phonesex in your apartment. -True confessions of a pest control operator. [Mf] [Mast] [Str8]

I had phonesex in your apartment while you weren’t home while I was supposed to be working. And it was amazing. -Pest Control

A few years ago I was a pest control operator servicing the metro area. Most of the time I stayed extremely busy. Busier than I ever wanted to be really. But in the winter things slowed down a lot and sometimes I would find myself with a lot of extra time on my hands after finishing an appointment. One day I did something so incredibly sexy hot and totally risky I still get turned on thinking about it or talking about it.

I had a lot of large accounts with large apartment complexes where I serviced about 100 apartments every 3 months on a rotating schedule. Units to be serviced were given a written notice 24 hours in advance to let tenants know I would be in their apartment. The management gave me the keys to the units and most of the time sent a maintenance man with me knocking on doors letting people know we were coming in to work. Sometimes we’d go in a unit and it was obvious people forgot we were coming. They’d leave out their bongs, sex toys, sex swings, all sorts of personal stuff people don’t want you to know about them. Every now and again we’d accidentally walk in on people having sex, or there would be some college girls running around in just their underwear getting ready for class. It was such a socially exposing job. To be all up in other people’s shit. Sometimes if people left a joint or a bong and some weed out- we would smoke it. Read more »

[Fm][Femdom][Chastity][Bondag][Waxplay] The Dentist

Hi,

My mistress wanted me to post a story publicly. She makes me write out my fantasies as a punishment, but I wasn’t attentative enough lately, so I had to share one as well. I hope this is the right sub to post it in. This is the first time I ever posted something or wrote a short story like this.

Hopefully you will enjoy reading it.

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**The dentist**

Going to the dentist expecting it to go like any other appointment. When I enter the room and sit on the dental chair it seems like any other routine check. The dentist asks me to open my mouth while she puts on latex gloves. She checks for any cavities and other oddities and informs me that one of my wisdom teeth must be removed. I ask if it would hurt and if I need any anaesthetics. The dentist nods and assures me it’s just a local anaesthetic. She asks me to open my mouth again and with a syringe she applies the anaesthetic nearby the tooth. However, I immediately feel my body becoming heavy and my mind starts drifting away. Read more »

Comparison Shopping (Gay)

As Tyler looked down at my hand dangerously close to his cock, he could have went either way. I felt confident that locking the door was a good sign but wasn’t sold yet.
“I am so jealous of you, or maybe just horny.” I said as I pulled the dildo away from him.
” Well”, he said with hesitation, trying to think of the thing he wanted to say. After a small delay as I walked around the counter, he finally thought of his next move.
“Let’s find a dildo that looks like you.”
“I don’t know, in comparison my little 6 inches ain’t much. ” I said jokingly .
“Let’s see, we can find a match, I guarantee it.” He said hastily.
Before I knew it I was unbuttoning my pants and unzipping. I folded down my underwear exposing my 6 inch cock. Although not as long, it is plenty thick.
“Very nice!” He exclaimed while either subcontiously or on purpose licking his lips.
” Let’s go to the wall.”
He would stare at my rod then look back at the wall. Finally he grabbed one, pulled it out of its case and pushed it against my pelvis. It was exactly the same length.
“Not sure about the girth” he said.
Yeah I can’t tell just by looking.” I say as I put one hand on the base of my cock and one hand on the base of the dildo.
“I think I’m thicker” I say with a grin.
He reaches over and grabs me and agrees.
A shot of adrenaline runs through my body at his touch.
He holds my cock for a few seconds and kind of runs his hand down the length of the shaft as he lets it go. We awkwardly stand there for a minute. I need to break this awkward pause. I say, “I am still not sure about that cock, I am afraid it is too big. I have never had a guy or a dildo that big. I would hate to buy it and it be too much because it ain’t cheap.”
He piped in and said, “well, I know a way you could compare it to your normal experience without buying it.” I played dumb, ” really” I said with a confused look on my face. ” Yeah, there is a shower in the back, if you want to we can hop in and get cleaned up, then you can test me out.” I rub my hand down his muscular chest and stomach and grabbed his pants by the front and walked him to the back as if I had any idea where I was going. Once in the back, I took his clothes off revealing a body that made me almost cum at it’s sight. He was in great shape, with abs sitting rock hard across his midsection with David muscles running down his hips to his large bulging slab of meat! He then disrobed me revealing my dad bod. If he didn’t like, I never would have known. We jumped in the shower and washed quickly. We never kissed or touched each other beyond our bodies rubbing together as we bathed. We got out and dried off with old t-shirts that never sold in the backroom.
When I had dried off I dropped to my knees and he grabbed my head and violently pushed my face all the way to his body. I gagged on his long thick cock. I pulled off and started bobbing on his cock. Deep, long strokes, rolling my tongue around the shaft and head. I would pull off and lay my tongue across his balls. He moaned and would pull my hair. After sucking for a few minutes, I slipped a finger in his ass. At this point he really began to moan and he really started talking dirty. Around this time I tasted a bit of precum and knew it was time to move on.
In one quick motion I spun around and buried my tongue in his ass. He grabbed the shelf in front of him and spread his legs to give me access. I rolled my tongue around the hole, and would place my tongue as deep as I could go and roll it all the way out.
He moved over to the bed the night employees could use and laid down. He reached under the bed and grabbed some lube. He poured some in his hand and smeared it over my cock and the rubbed two fingers worth of the lube up his own ass. I raised his legs over my head and he help glide my cock inside him. He was tight and firm both anally and everywhere else. He rested his legs on my shoulder as I played with him with one hand and felt his abs and chest with the other. I could feel as I thrust deeper and deeper in his sexy ass that I wasn’t going to last much longer. “Can I cum on your cock?” I breathily said, trying to keep from cumming. “No” , He said, “Fill me up, baby!”
When those words came out of his mouth I could feel it coming on. His legs fell to the side as I leaned forward to really thrust. I was surprised as I leaned forward and he caught me with a big, wet tongue down my throat kiss. As I felt his tongue, my dick exploded and I laid on top of him for a moment just humping the last bit of cum out into his tight ass.
He rolled me over and grabbed the lube. As he stood up, I could see my cum run down his leg but he did not stop. He slathered his cock in lube. I rolled over and stuck my ass in the air expecting two fingers of lube. Instead I got two lips pressed against my little hole. He licked me inside and out. Making passionate love to my ass with his tongue.
Then I felt two sticky fingers enter me and begin to massage me. I laid with my face in the bed on my knees with my ass in the air. He then pulled me to the edge of the bed and pulled my legs off to the floor. At this point I was bent over on the bed. I spread my legs and he pushed all of him in me. It was a glorious mix of pain, pleasure and excitement. I felt alive! He fucked gently to start but became more aggressive as he bred me with his hands holding my hips in deep and strong strokes. He fucked me on my back and kissed me as he did when was on top. But when I mounted him, he really began to moan. I stuck my fingers in his ass as I bobbed up and down. I could feel my cum still in him. He played with my cock as I took all 8 1/2 inches. Until he seized up. His abs were tight as he let out a primal moan and I felt all his passion explode in me. I fell on top of him in a sweaty heap.
We put our clothes back on and I went out to the storeroom. We had broke the “be back in an hour” sign and lucky for me my wife had fallen asleep. I said “I’ll take that big black cock by the way.”
He laughed, “I think you already did.”
I left with a dildo close to his cock but more importantly, his number. So now I can close my eyes when my wife is fucking me and it is pretty close to Tyler or I can give him a call and we can “go catch a game” and I get the real thing!
So while online shopping is convient sometimes you just got to compare products in person and maybe even give them a test drive!

[f][M][Str8] 38M High School Teacher having “inappropriate” relationship with 18F Student

First, my particular fantasy really is in regard to an 18 yr old. I know that’s kind of become a fad to say “18” and when you’re really just avoiding filters, but my fantasy really is for 18 yr olds specifically because that’s when teenagers have legal responsiiblity (that last statement will make sense later.)

Oh and for the record I do not have kids ***nor*** am I a teacher, lol.

Last warning: This story/fantasy touches on being a bit masochistic. NOT violence, no rape or anything like that, just on the dark side, especially at the end.

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My fantasy has been to take advantage of a naive 18F student in my class. My fantasies always play out in my head a lot like I’m watching a movie. i.e. — I always imagine my POV would be like a camera surveying a scene. In this case, it’s after class, schools deserted. The parking lot is empty aside from my truck in the back of the lot. Read more »

Comparison shopping… (Gay)

I stood there feeling vulnerable. Staring blankly at a wall, looking like a complete idiot. It is one of those moments when you know you have stared too long and you wonder what the fuck is wrong with you. But purchasing a strap on for my wife without her there was a new choice. I came out to the store at 1:00am to avoid people and of course it was just me and a store clerk.
I guess Tyler, the store clerk, saw me in my state over overthinking and slight embarrassment and he came over.
“Hey there” he said.
I simply nodded my head never looking away from the wall.
“You know what your looking for?”
My confidence was shook due to my awkward wall stare. I was not new at this but something about doing it alone threw me off.
“I’m looking for a peg, well really a strap and about a 6 inch dildo. Looking for more of a brief style harness than an old school nylon strap and pad system.”
Tyler laughed, ” Judging by your blank stares I thought you were lost but you seem to know what you like”.
I turned for the first time to look at Tyler and a little giggle slipped out like a girl with a crush. Tyler was tall, black with shoulder length dreadlocks. He was in his mid 20s and very handsome.
“Yeah, I know you probably see a lot of middle aged white dudes come in here for this. ” I joked. I, being a 40 year old white guy myself.
” Yeah it seems to be the new trend for a lot of guys.” He said.
” Well I was anal before anal was cool. ” I said trying to make a joke that fell flat.
Well yeah, said Tyler awkwardly, let me know if you need any help.
“Shit” I thought. “And that is why your wife has to peg you because there is no game left in you.”
I quickly pulled down a harness and a 7 inch black cock… Not for any purpose, just kind of subconsciously. Then I moved on to the lubes and picked up a new bottle as well as a new bottle of toy cleaner. I made my way over to the costumes and lingerie. Considering a little gender bending but decided to wait and purchase that from Amazon or Yandy due to price.
Content with my selections I head to the counter. Tyler awaiting my arrival asks me if I found everything I need. I said “I guess”, which is my common answer for anytime I am asked that. Tyler looks up at me and said,
“Come here, let me show you something.”
He grabs the dildo I chose off the counter and walks back to my wall of awkwardness.
“This dildo is fine” he says, ” but if I were you, I would move up one inch. You see one additional inch on the length creates about a half inch on the girth at the base. You are going to want that girth, trust me. That is my dong of choice” he said with a smile.
I said, ” Well you can’t fight experience. That is a lot of cock though. ”
“Nah” , He said laughing,” That is basically the same size as my cock and I never hear complaints. Just take it easy to start. ”
Thinking he may show me, I challenge his cock size. “C’mon man you don’t expect me to believe you are that big?”
With a smirk on his face, he said ” I don’t care what you believe.”
“Oh, okay” I said hoping he was picking up on the flirting.
He sat the dildo down on the counter and started walking to the front door. He locked the door and turned off the open sign putting out a sign that said he would return in an hour. He flipped the front lights off and walked back to the counter.
“Fine!” He said defiantly.
He reached down unbottoned his pants, and as he unzipped his pants, his erect cock was pushing against the zipper. With one quick zip, without the restriction of underwear, his big cock shot out of his pants.
I stared, feeling my erection continue to grow. It was a thick, long and beautiful cut cock. It was hairless and spectacular. I looked up at Tyler and he said, “I told you” .
I didn’t want him to zip up but I also wasn’t sure about grabbing for it so I thought of the only thing I could do. I grabbed the dildo and took it out of the plastic case. I came around the counter and pressed the base of the dildo right along side the big black cock allowing the backs of my fingers to bump his dick. He had it beat by about a half inch.
My mind raced… I wanted him…. Bad! But how do I get there.
Find out if I do and how in Part 2….

Talking with a married couple…

This is what I sent them, rolled off the top of my head. Thoughts, comments and kind suggestions on my writing skills?

I eagerly knock on your door to begin to notice my young cock is already stiffening from anticipation. I think to myself a quick image of me with a fistful of the wife’s hair in hand, fucking her face so hard she’s slobbering all down her tits.. her mascara is running down each of her flush cheeks. Her eyes looking up – basically rolling in the back of her head – make contact with mine and she gargles something with my cock in her throat clearly trying to speak. I don’t care. I keep skull fucking her as she gasps to tell me something rather annoyingly important. After one long full push, holding myself in the depths of her throat… I yank my cock out grab her by her throat and slap her hard on the cheek and I say “now what is so fucking important, that you had to interrupt me” she looks up in a high-pithed, innocent, apologetic voice and says “Please come fuck me every night like a dirty little slut, make my husband watch.” Then a noise breaks me out of my trance, and you both stand there husband and wife… with warm inviting smiles – as if we’re meeting for dinner… not knowing how rough and intense this young cock is going to destroy all of the Mrs holes.