Teddy and Kitten: The First Date [MF] [M36 + F23] [long] [cheating]

Disclaimer: I know this isn’t particularly steamy, but perhaps it’ll pique your interest and give you enough background to want to read the second date, where it crosses a lot more lines.

I’m sure we all remember Yik Yak, that beautiful anonymous app that allowed us to speak our minds and be judged for our mistakes. Being in Boston, the community was vibrant. There were shenanigans, major league fuckups, desperate hookups, and most importantly, the establishment of alter ego characters. We’ve all been there, used our keyboards as masks and became someone we dare not be in real life. I became the sarcastic troll that is my constant inner monologue, whereas what everyone else sees is a driven student, well rounded, big dreams, some past struggles but the strength to overcome anything.

[MF] Laura gets fucked in the frat house, and not for the first time…

So, when I was in college, I lived in a fraternity and we had a sister sorority down the street who we did mixers and all that kind of stuff with. Most of the girls were your typical sorority slut/bimbo/ditzy type, but not Laura. Laura was from the Midwest (this was an East Coast school) and she was the kind of girl who smoked cigarettes, wore all black, had tattoos, and short black hair. She had firm, peach-sized tits, which she let show through her thin tank tops. She usually wore skinny jeans or sometimes a mid-length skirt at parties, but she never quite fit in. She was pale, and not exactly quiet but not outgoing either.

I knew that she put out, she had a bit of a reputation and at least two guys in our fraternity had fucked her before. Additionally, that reputation included the fact that she squirted, and that she usually didn’t make guys use a condom. So, stupid man-slut that I am, I decided I was gonna make it happen. I waited until we had a party one weekend, and when I saw her (we knew each other through friends pretty well), I told her to wait around until the afterparty. I know it sounds dumb, but our afterparties really were something people wanted to stay for. We always had coke, and plenty of booze leftover, and things would always get a little wilder.

Shy meeting with an escort. [MF]

So my 19th Birthday was on the horizons months prior a friend developed interest in us having a sexual relationship. I turned her down though due to barley knowing her a month at the time. Later from that she says it was a good idea nothing happened because I was more like a sibling than anything.
Anyway nothing ended up occurring between us. During this time I was away in a new town. I didn’t have any close friends and didn’t know much of the town at the time so I was quite lonely and anxious. So my Birthday is approaching in a few days and I haven’t done anything sexual at the time I really wanted to try foot worship/play more than anything. I spent quite a lot of time browsing the web and up on an escort site.I called this 22 year old Honduran girl that was the most recent post on the site

I was nervous and standing outside wanting to make the call away from where ever people could hear. I explained to her that I was just interested in feet worship/footjob and nothing more. I told her I was just a regular college dude and she agreed to meet me for $40 and to call when I was near by.

I get older [m], and [f]reshmen stay the same age (long)

Hey y’all I’m back. This night of sexytime happened a couple months ago in my senior spring of college. At this point I had given up on standards and was enjoying the libations of alcohol and women regularly. All my roommates after 4 years of school had gotten hitched up with girlfriends, but I was as single as could be (see my previous post). I had a FWB but at the end of the year she was more focused on hitting the books rather than my cock.

So cue a Saturday night, as I’ve mentioned previously my roommates were on a co-ed sports team, and they had just returned from a meet, which they had won. So the team threw party at a house in the college neighborhood not far from my house. Now I enjoyed these parties because the girls were very hot (college sports do that do a women’s body) and the beer flowed freely. Usually is stuck to the cheap Natty Light, but for their recent win the team had splurged on some harder stuff. After a couple shots of vodka with a good looking classmate named Beatrice, Kate (the girl I had cheated on my ex with) texts me. Now Kate is definitely crazy and is on a different sports team than the one I was partying with. Kate was hot but senior year and alcohol had gotten her a little too chubby recently. I politely responded that I was at the party but was planning on staying while.

A fun day with my boyfriend [MF]

I apologize in advance for shitty writing!

I went over to my boyfriend’s last week. I had told him some things I wanted him to do, controlling me more, telling me what to do, being rougher, choking me, and spanking me.

Well on to the story. I got over there and he’s sitting in his room. I walk in and I’m wearing the bra and panties he asked me to wear for him. I lay down and take off my pants, start touching him some, and then I take off my shirt. He puts down his game and starts really paying attention to me. We lay back and get cuddled up and comfy, I’m rubbing him though his pants and he has my panties pushed to the side. I asked him to take off his pants and he said “take off yours first.” I took my panties off as fast as I could and he kept fingering me. He pulled me on top of him and guided his dick into me. I started bouncing on him and he started thrusting from the bottom harder into me. He took off my bra and threw it to the side, and then took off his shirt. He pulled me down to him and started thrusting harder again. He kissed me though this time and bit my neck and ears. He pulled my hair and pulled my head to the side and kissed down my neck and bit my collar bone and shoulder. He spanked me hard while I was on top to make me gasp. He grabbed my ass and squeezed it hard. Then he sat me up and bit my nipples while still thrusting into me. He moved his hands from my boobs to my throat and choked me and pulled me down harder.

[MF] I ended up having a lot of sex with a co-worker! Good times….

Alright guys, I’m typing this out for the second time tonight… My phone died during the first draft… This story will be in 3 parts!! I hope you enjoy!!

So, towards the end of my first year of teaching I had a bit of an agreement with a co-worker (chris is how I will refer to her now)… Chris was Latina and 5’4″… She was the best kind of curvy a solid C cup with an ass that was out of this world!! And, while I noticed I never thought of her as anything but a co-worker… We were both prone to carrying our workday stress in our shoulders and seeing as both of us were quite skilled at massages we would help each other out a few times a week (damn I was dumb back then… I should have seen all that follows from a mile away).

I planned to stay for lunch, ended up staying overnight. [FM]

Long time lurker and I decided to share my fondest memory. It’s been lying in my drafts for around a year, and I think I should share it. I’m not good at writing but hope that I can do as much justice to the whole memory as possible.

It all started when I was in the midst of packing to move across the world. Long story short, a lot of things were going on at home, and it wasn’t feasible for me to stay where I was. In my hour of boredom and anxiety, I decided to post a dirty personal on Reddit. There was a flood of responses and most sounded creepy or just weird. You know, the wrong kind of weird that a girl would want to stay away. Amongst those messages was Harry’s- I took a liking to his short and polite message and decided to respond. He also mentioned something about cocktail making. Heh, *cocktail*, get it? I’m lame.

[MF] Submissive girl I met on Craigslist gets her asshole filled with cum for the first time

A few weeks ago, I was browsing through the lovely corner of the internet that is the casual encounters section of Craigslist. I’ve had a handful of successes on Craigslist, the trick is to just sound like a real human and prepare for 99% of the responses to be either robots or people who are clearly lying about who they are.

I came across this one post that said she was looking to be used, and it didn’t follow any of the clear spam bot formulas. I sent her a brief description of myself, a picture, and a link to the part 1 of my last story as an example to show her what my definition of “using her” was. She responded back to me, and we ended up going back and forth for a while about things she was interested in trying. We traded numbers, and started chatting a bit more explicitly.

[MM] Seduced by an Older Dominant Man

Hey guys Not sure how many of you like [MM] stuff on here but thought I’d share this experience! I’ve been wanting to type out this experience for a while now. This happened about 2 months ago and was probably the hottest experience I’ve ever had. I just recently turned 20 (slim,tall,indian,from USA) and have had 1 relationship and 2 flings with 1 being on grindr with a younger person as well…So still relatively new.. I was on grindr and was contacted by an older gentleman (46 yr. old, White, muscle, hairy). I had been looking for an older man before then but was pretty picky about seeing the right one. So we started chatting and things got pretty heavy after a day or 2. We had scheduled a meet up a couple days later because his place was a little drive from my college since I was away from school when he found me on the app.
I seemed at easing chatting with him on Grindr and I told him about my sexual preferences. He fit the bill for me. Stocky, somewhat tall, thick thighs, broad chest.. I also said that I’m really into white guys so he proceeded to send me a bathroom body pic with a girthy white cock in his hands. I melted a little :) He seemed a little aggresive with his messages.. for example “I want to make you my little brown sex toy” and things of that nature, maybe I’m not experienced yet but I haven’t gotten messages like that certainly when we haven’t met yet, but I found it kinda hot.

Unexpected fun from an uber driver [MF]

This happened a couple months ago. I was in town for a business conference sort of thing and since I live in a small town I scheduled a doctors appointment while there.

The doctors office wasnt too far away from the conference but it was pretty chilly so i decided to take an uber. I noticed my driver was pretty cute which had me excited as i waited for her.
She pulls up in a red Jetta and when I get in i instantly notice her amazing bright green eyes. She was a little on the thicker side but had a great smile and from my limited view had a pair of nice tits. I usually sit in the back seat when using uber but decided I needed to sit in the front seat once i saw her. We exchanged the usual pleasantries and off we went.

We get to talking and I found it very easy to carry a conversation with her because of how outgoing she was. After a couple minutes I start to notice that according to her gps we still had 10 miles to go but the office was suppose to be 5 miles away from where she picked me up, but I’m enjoying our conversation so much I dont worry about it fees be damned.