Anal Archives — Page 764 of 957 — NSFW story

[FM] Really Real Estate

Let me start this off by giving you folks some background on me. I’m doing this for a couple of reasons, one – because I think you need to know this stuff in order to understand the magnitude of why this was such an atypical situation to happen to a guy like me, two – because I’ve been an active Redditor for over eight years and I have a strong belief in giving *something* back to the community, and three – you can decide in the next minute or so if you feel like wasting your time reading this wall of text. Oh yeah, four – If you did read this, I’d like your input and opinions on things, after all, that’s what we are here for.

Sexy Party

Last night?

It was time for a sexy party. I even wore a costume. Yes, me!

Jonah got pressed into volunteer service at a Burner-run play party last night. We decided to go to play before that volunteer shift. Am I glad we did! There was an anal play workshop that was extremely educational. Although every now and then, I love anal play, it’s complicated for me. I have quite a lot of pain when I have anal play, and fear of pain makes me hesitant and nervous about anal play unless I’m so utterly turned on that I’m the one craving it. With Jonah, that’s never been as issue, but I find that so few men really understand anal play. So, yay for sex education! Read more »

Three Times a Charm [marriage]

“So go ahead tell me what happened, Natalie.” Trevor sat on the couch with arms folded looking over at her standing by the window. They had been fighting for hours, after Trevor found out that Natalie was upset about their daughters grades.

“Why won’t you face me?” He said rising from the couch walking towards the window. Natalie looked out to see a gloomy day of haze as she began to regret being with Trevor.

“I can’t Trevor you mean nothing yet everything to me.” She said as a crumbled paper fell from her hand. Trevor quickly picked it up then saw it was divorce papers. He threw it back to the ground then grabbed her by the shoulders.”Give us a chance, please!” Sorrow set in his gray eyes as he began to cry uncontrollably. Natalies eyes were vacant of love but he kept searching through them for compassion. She closed her eyes tight with one tear trailing down her cheek.
Placing his hands inside hers, she began to tell him why she is leaving.

“I watched you fuck the 18 year old girl Abbie on my bed.” Squeezing his hands tighter she kept on. “I watched you fuck Brian in our car in the parking lot.” His eyes became transfixed on hers as anger radiated Natalie’s face. Read more »

Daddy

I waited downstairs by the car like he told me too. A long trench coat kept the rain off my body but kissed my face with tiny drops. Looking back at the door I saw him running to the car to let me in. I sat in the back wondering where he is taking me. The front seat was for good girls only and I had been so bad. He looked in the mirror at me with a stern face while driving . I became shy, putting my head down while fumbling with the straps of my purse. The car came to a stop which made me peer out the rain soaked window. Beautiful lights sparkled like diamonds as I began to assume our whereabouts.

Daddy escorted me from the car then placed a rhinestone collar around my neck. I looked in his eyes with a slight smile as he gave me the good girl collar. Daddy likes to give punishment for bad behavior which is a whole night of nipple pinching and paddling. I knew I had done something bad yet he flashed me a smile then grabbed the leash. Read more »

Weekend Vacation – Part 1 [MMF][CUCKOLDING][LONG]

I hope you can forgive bad formulations and mistakes, English is not my native language.

How I was cucked by my buddy Karl for the first time after losing a bet to him you can read [here](https://old.reddit.com/r/cuckoldstories/comments/9b97nw/wager_with_an_old_army_buddy_mffcuckoldinglong/).

And how my wife arranged for me to be cucked a second time on our wedding anniversary, I posted [here](https://old.reddit.com/r/gonewildstories/comments/9bvyiw/anniversary_surprise_mfcuckoldinglong/).

After those two stories happened, I was cucked a few more times by Karl, after losing other wagers to him, and once or twice my wife arranged for me to be cucked. While those sessions were just as enjoyable it was nothing new. I have one cuckold experience left though, which is interesting enough to post it. So here goes:

So my buddy Karl, his long time girlfriend Christine, my wife Clarissa and I arranged for a little vacation. So we booked some rooms at a hotel in a big city for a weekend, from Friday to Sunday. We checked in and unpacked. After that we went out, shopping, sightseeing, drinking and whatever else you do on vacation in a big city. Read more »

A Memorable Fuck

At fifth and third street, Julian sat on the bench waiting for his next trick. No formal address, working as an escort in Las Vegas for the past two years. Reaching to get a cig from his pants pocket he thought about the fuck he had last night. The school teacher with bouncy breasts who paid him five thousand dollars to fuck her anal and spray cum on her face. Last night, made him reconsider the idea of quitting. The money paid for everything he could ever want because working in an office cramped his style. Waiting patiently, a black sedan pulled into his view. The hook-up came from back page and from the looks of her picture she needed a good fuck. Dabbing the cig on the bottom of his shoe, he got up and approached the vehicle smiling in a childish way. A foot from the passenger door, it opened revealing an attractive blonde with huge tits and a curvy frame. In awe of her aesthetic, he checked the cell to see the picture again. She looked different from what he seen previously which made him tilt his head in wonder.“Your name is?” Julian said while leaning against the car.“I’m Diana the CEO of Rosenlock Cosmetics.” She said while rubbing her breasts looking in his eyes.“So, what did a woman like you want to do with a guy like me tonight?” Julian said moving in close to her neck to lay one kiss.
“Oh, you move fast, well my apartment is right here so let’s go upstairs and get to know each other.” Diana said while moving with sass up to the apartment door.
Julian watched her ass move like a milk shake as she walked up the stairs to her apartment. She turned around observing him right on her ass. “Sorry I was making sure I didn’t lose you.” Julian said as he ran his fingers through his dark long hair. She smiled back at him then opened the door to her apartment. Stepping inside, he noticed luxury chairs dripping in gold and plush white carpet. Her apartment looked like a palace fit for a queen. She told him to have a seat while she put down her things. Julian sat on the white couch that felt like velvet. As he admired all the gold relics in her apartment, she emerged from the bedroom door in a black robe.
“Are you comfortable Julian?” She said moving closer to him sitting on the couch. Julian was intrigued by her beauty. Her nipples pressed against the robe making their own impression. She noticed his eyes panning down at her big breasts, so she opened her robe. Her breasts were full youthful and perky.
“Wow, your breasts are amazing I love them already.” Julian said squeezing each one while she smiled broadly at his comment. Going in for a nibble on her breasts she pulled back and closed her robe. Confused by her action he moved closer to put her at ease.
“Julian how much money do you want because I am a unique kind of woman?” Diana said as she started to part her legs to invite him in.“Well depend on what you want me to do, but I will take ten thousand if that’s ok?” Julian said as he began to unzip his jeans while sitting on the couch.
“How about sixty thousand now and ten more after we finish?” She said spreading her legs open even more. The more she talked about money the harder he got. Cock stiff with lust he got close to her and rubbed in between her thighs. Soft moans led him on a chase for her sweet pussy lips as the two got closer exchanging exhales. Then as he got closer to her lips, she whispered into his ear. “Julian suck my cock.” Julian moved back quickly from her lips then stood up as if he had just woken up. “You are a man?” Julian said moving back slowly as she tried to grab for his hand.
“No, I just have a cock but I was born female.” She said putting her head down slowly then looking back up to see his expression.“Look I never sucked a cock before and it won’t be today.” Julian said trying to zip his jeans back up.
“Julian I’m sorry, I will put the money on the kitchen counter take it and again I’m sorry for wasting your time.” Diana said as she laid the money down returning to her room. Julian looked at the money then grabbed it heading for the door. As he went down the stairs with a feeling of disgust he paused upon reaching the last step. What are you doing Julian she is paying so much just for one night. Thinking about it he decided to head back up the stairs to at least comfort her.
“Look I am sorry please open the door.” He said waiting for her to open the door. Peeking out with fear she let him. She sat on the couch with an erect cock stroking it as she spoke to him.“Do you want to be here Julian?” She said rubbing her cock up then down.
“I never done this before but there is something I like about you.” He said while sitting next to her on the couch watching her stroke with urgency.“Maybe start slow Julian, suck my nipples while I stroke my cock.” She said taking off her black silk robe. Her long hair reached to the perky nipple as Julian sucked it slowly. As he sucked her nipples she stroked even faster making Julian hard. His cock tented up in his jeans as her strokes made him drool onto her nipple.“Oh yes, Julian suck my cock baby.” Julian hesitated but his lips wanted to feel her fat cock in his mouth. He went over to her then placed his lips on her wide fat cock. The size filled his mouth as he sucked deeply into his lips. Her moans intensified as she rubbed her nipples watching Julian sucking. Aroused with curiosity he kept sucking her cock as if it was meant to be. She gently started to pump her cock inside his mouth making her moan loudly. Turned on by her body Julian unzipped his jeans and began stroking his cock as he sucks hers. Julian had never been this horny in his life and wanted to fuck her so bad. Knowing his desire, she slid her cock from his lips then turned to sit on his cock.“Julian fuck me dirty baby.” She said while easing onto his hard cock. Sliding up into her anal he began a slow fuck as she grinded on his cock. The tightness made him fuck her slow as she began to grow with excitement. As he fucked her anal she began stroking her cock again which turned on Julian so much. Stroking faster her cum exploded wildly into the air which made Julian come inside her anal. The climax exhausted him yet he wanted more. Sliding off his hard cock, Diana stood up rubbing her cock and then put back on her robe.“I guess you will be leaving now, people usually fuck me and go.” She said with sadness in her eyes walking towards the door. Julian rubbed his cock and began to put back on his jeans. Gazing at her watery eyes he threw his jeans back onto the floor.
“Nah, I am not leaving we are going to do this again in the shower, are you ready?” Julian said grabbing her by the hand running to the bathroom.

Jenna Gets What She Wants Part 2

[https://www.literotica.com/s/jenna-gets-what-she-wants-pt-02](https://www.literotica.com/s/jenna-gets-what-she-wants-pt-02)

It was Thursday morning, the day after Jenna had been sodomized by her math teacher Mr. Reed and Principal Brooks. She was nervous, but also excited, about the prospect of seeing either of them today. Would they exchange glances, or even words?

Jenna opened her locker to find an envelope addressed to her. She checked to make sure nobody was looking and pulled out the note inside, unfolded it read it.

“My office. 11am.”

She could only assume it was Principal Brooks who had written it, and that he wasn’t done with her yet.

Sitting down in her first couple of classes that morning proved difficult for Jenna. Her asshole had taken quite the pounding, especially by Principal Brooks, but her time with Mr. Reed had been her first. It was sore and hurt when she sat down, so she shifted uncomfortably in her seat for almost the duration of her classes, hoping nobody would notice. But someone did.

“You OK there, Jenna?” asked Mr. Lewis, her chemistry teacher.

“Yes sir,” Jenna replied, embarrassed that he had noticed. Read more »

The Roommate[mm][bj][forced gay]

My hand gripped my shaft tight, the lube gushing between my fingers and my laptop sitting high on my chest. My roommate Matt would be out for hours so I had taken my porn to the living room to enjoy a good fap before bed. There was something dirty and exciting about being in the common area naked. I had only known my new roommate for about a month and we haven’t talked very much. All I really knew about him was that he was gay and he loved going out to this club downtown to meet guys. He would come home most weekends with at least one guy who would stay until the early hours of the morning. Our bedrooms were next to each other and the walls in our apartment were quite thin. I could hear him groaning through the walls and from the sounds I heard he loved giving blowjobs. Read more »

Fifty shades of fun [MF] [mdom]

This happened a few years ago, with a past partner. Quick descriptions: me, 6′ tall, dark hair, trim, 7″ in both length and circumference; her, 5’4″, strawberry blond, perky C cups, and into martial arts. Both in our early 30’s.

Her kid was with her ex for the weekend, so I came up with a plan.

I had already trained her to do what I wanted without question, so when I gave her instructions, she would obey.

> Go to [X] trendy hotel in our city at 5 PM. Get a room, and tell them to leave a key card in my name at the desk. Go to the room, get naked on the bed, and blindfold yourself.

She’s a good girl. The hotel has a bar mostly of of sight from the front desk; I got there a little bit early, and watched her nervously check in while I was sipping Bourbon. After I was sure she had time to get ready, I grabbed the key card from the front desk, and headed upstairs to the room. Read more »