Repost: Hostel Hook up 28 [M] 23 [F]

Fresh off a recent break up, I went on a solo road trip to take my mind off things. My first stop was a hostel in the city. Unfortunately, the first night was so lame that I would have bailed had I not pre-paid for a second night. Day two was better. I enjoyed the sights and planned for the evening in case I couldn’t find anybody to hang out with at the hostel. Fortunately, I wouldn’t need my backup plan because the hostel delivered.

Upon entering my shared dorm that afternoon, I was pleasantly surprised to see a cute girl alone in the room. I introduced myself to Erin who was lying prone on a top bunk propped up on her elbows reading a magazine. Her strawberry-blonde hair was still wet from a shower and mostly blonde thanks to the bright sun shining in the window. She wore yoga pants and a low-cut tank top that gave me a down blouse view of her small breasts and bra. Her adorable smile and thick Irish accent melted my heart. Read more »

[M]y best [F]irst date ever [long]

This was during my time in college, so it has been a while, but I still remember this quite well. A little background: Anne and I became friends our second to last semester. She was cute, but had a boyfriend, so I never really tried to flirt or anything like that. One day when we were checking out our midterm grades (same course), we decide to have lunch, where she confessed that she really liked me and that things weren’t going to well with her boyfriend. I comforted her as best as I could without crossing boundaries. We started talking more, texting, flirting, etc. It was hard not to ask her out, but she needed to take care of things on her end.

Eventually, I broke down and asked her to go to the movies with me after finals. She agreed and the day before, she breaks up with her boyfriend. The day of, I meet her on campus with a huge smile on my face. We hug and go to the movie theater.

Sexy stuff starts here ******** Read more »

I’m 37 and fucked a 19 yo from Instagram. [MF]

This all started on Instagram. I was going through a transitional phase in my life; my then wife and I were looking to relocate to a different part of the state on our days off. We’ll call the new city Middleton. During one visit to Middleton I spotted an old car that caught my attention so I took a photo of it and posted it to Instagram and hash-tagged it #middleton. Read more »

First Time Without a Condom [MF]

I definitely had a huge change of heart about condoms a few years ago and never went back. I was about 19, and a Freshman in college. The year had been hard on me being away from my very beautiful Israeli girlfriend who had been accepted to another school. We had been dating for all of our senior year of high school and were doing our best to make it work long distance. She was a virgin when we started dating and was hesitant to lose her virginity. After months of dating and doing everything else except actual penetration, she was ready. The condoms we used were very basic, but I knew them to be very sturdy (so as to put her mind at ease.) It was a beautiful experience, and one I will never forget. She was shaking as I penetrated her for the first time, gently shushing her and kissing her softly until I was deep inside of her. We went slowly and after maybe 20 minutes, we both orgasmed and collapsed. Now, though this is a fond memory, it’s not one I like to look back on too often. Of course, halfway through the second half of the semester, she dumped me…. Read more »

Blackmail – pt.3 [MF]

She heard steps entering the room. She remained still. Naked. Exposed. Her breathing faster than before. *It has to be him*. Finally after so many weeks of games they were in the same room. He didn’t close the door yet. It was not important. He stood closer and touched her hair. She whimpered. She kept quiet. He touched her nipples and she tried to be silent. He whispered in her ear. “So here we are”. His warm breath brushing her neck slowly. Another woman entered the room, but she didn’t noticed. He closed the door and walked back to her, kissed her cheek. She could barely stand.

“I was thinking about that night after you bought your toys…did you bring them?” She did. They were inside a bag on the bed, he took them out. The other woman remained unnoticed, her legs a little spread on the chair. Smiling and waiting for her turn to speak. He continued, “that night you did everything as I told you, I guided you and you enjoyed it, probably you never had an orgasm as strong as that one”. It was true. *I loved every second of it*. Such shame afterwards. Read more »

Showing off her [M]outh skills for her [F]riend

It started innocently enough, she and her friend were joking about some other friend who said she hated giving blowjobs and one of them declared themselves to be completely in love with giving head. That would be the girl who sucked my dick almost daily.

They didn’t think I could hear because I was in the kitchen and I tended to not pay too much attention when they were gossiping about their friends.

But, hearing her say, “what’s not to love about sucking dick?” made my ears perk up. “It’s fun, easy, and tastes good. And he loves it.”

I couldn’t hear her friend’s exact response, but it was clearly the same sort of enthusiasm for fellatio.

I was hard. I leaned against the counter silently, listening to them extol the virtues of being good little cocksuckers who swallowed and practically begged for the chance to service on their knees. I gripped my cock over my jeans and even gave half a thought to jerking it right there while they were talking.

Instead, I was interrupted by my girl call yelling out my name, asking what I was doing and if I could bring her a drink. Read more »

Covert Seduction [MF]

Her second drink arrives as she perches on her barstool and patiently observes her target, Victor Lancaster. Victor may not know that his company manages investment accounts for sex traffickers, contract killers, and other unsavory groups. He is a rainmaker, a moneymaker, and the company lets him do his magic. He’s the weakest spot in the company’s security armor.

Victor is good looking, better than many of Taylor’s assignments. He’s already got some gray, a bit early for a 35 year old man. He’s just over six feet tall, and fit. He’s wearing a perfectly tailored suit, stylish and sleek, with a slightly loosened tie. He’s got a roguish smile, the easy confidence of a man who has won at life repeatedly, and expects the world to continue to lay down at his feet. Taylor is ready to make her move, to reel in Victor like the arrogant fish that he is, but there is an obstacle. Read more »

[MF] The Catholic School girl shtick is a real thing [Long]

When I was first met Chelsea at my friends graduation party, she was alone in the corner petting the family golden retriever while browsing her cell phone. She was the daughter of a family friend, clearly looked like she didn’t belong at parties like this and it showed. Her awkward social skills weren’t helping my first impression. Thankfully, I don’t judge a book by it’s cover. Standing tall for a woman at 5’9”, she had a farmer tan with freckled skin, strawberry blonde hair with lots of sun streaks, long lanky limbs and an ass that would make any PAWG proud. More than just a bubble butt, it was an overly exaggerated apple bottom to the point of a “daaaamn”. Even sitting down, it was something that one couldn’t miss on her. It was by far the most pronounced feature on her body. Not at all proportional to her frame. Not gonna lie, it was why I took notice of her at all that evening. Read more »

The Start of Learning Something New [part 2] [MF] [BDSM]

He walks back over to her after spending some time in the drawer. He lays a handful of things above her head, Natalie tries to look up but he stops her head and places a finger in her mouth and pulls it back down. “No, not yet.” He takes her hands in his and places them above her head, then slowly makes his way down her body, a finger trailing down her skin. His finger slowing as it reaches her nipple and gives it a pinch. Natalie’s back arches as he applies pressure. Then his hand trails down the rest of her body, getting to her waist he moves his finger away from her wet pussy and down to her thigh moving down to each ankle. Taking a grasp on each spreading her legs slightly he pulls hard and quick to where her entire body moves down the bed and her knees bend under the beds edge. Read more »

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I didn’t Cum… But My Wife Sure Did [MF]

I don’t normally talk about me and my Wife’s Sexual exploits, but after the Crazy Day we had Yesterday, I felt like I had to share this one.

So we had taken the Kids to my Moms for Spring Break, so we have the whole house to ourselves till Sunday. Since my Wife works Overnights at her Job, I didn’t think she’d be awake to WAY later, so I went and Jacked Off after I got back. That was a Mistake, as it turns out she was awake before I got home. So we go out for a Bit, Get Lunch at our Favorite Sushi/Buffet, and get some shopping done.

But after we get home, we’re laying down in bed together, and she was Horny as hell. This woman can get Insatiable sometimes, so I have to be Ready to go at any time. She wasn’t happy to hear I had already taken care of myself, but Now that Several hours had passed, I Was at least able to get him back up enough to Fuck her, so we quickly got undressed, and she used her Saliva to wet me up, and climbed on top. Read more »