Conservative College Coeds’ Night of Sin [MF]

I went to an extremely conservative Christian college under some delusion that it would be like my highschool youth group. Ya know, where all the chicks are, hahaha. Ironically, the girls in my youth group had plenty of sexual deviance. My college was very different. Prude, homeschooled virgins for God made up the majority; and everybody is 18, lol. Pippa and I bonded over the fact that we were in the minority.

Pippa was a year younger than me. She had a boyfriend back home. She told me how they took eachother’s virginity and how she struggled with wanting to have sex more often but knowing it was wrong in they eyes of our peers, teachers, parents and God. Looking back, its been one of my biggest regrets, attending that school (DONT BOTHER ASKING). She told me these incredibly hot stories about she and her boyfriend. She’d tell me how nice it was to talk so freely with someone about ‘sex stuff’ and that telling the stories really turned her on.

I think about having children a lot more than I used to…[MF]

I found Erin on AFF. We were both in our early twenties. Before I decided to message her I perused her profile. Her pictures were cute, cute enough to  make you wonder if there’s a real person behind that account. Her blog of experiences in the lifestyle caught my eye. Topics range from ‘what’s it like to be the only unicorn in existence’ and ‘for real single men, get your shit together’.

We started chatting and eventually graduated to texting and then a voice call. I wish I still had the pictures she sent me from our initial chat. In them, she was wearing a black corset and the most adorable velvet choker. She had a little thing for soft BDSM; something I hadn’t explored in the slightest, at the time.

That night we talked on the phone got to know each other a bit. I asked her what she wanted and what she was doing on AFF. Her response aligned with my lifestyle. She pretty much reiterated my response to the same question when she asked over instant messenger: no strings. Purely sexual relationship if we click and like playing together. I don’t think I consciously caught it at the time but in hindsight I have always believed that she wasn’t completely honest with herself or me. – more on that later…

Ode to Craigslist: My First Milf [MF]

As I’ve mentioned in previous posts, I discovered the Lifestyle after getting dumped by my high school sweetheart.  Well, this is Genesis, the very beginning. Also, in light of recent events with the loss of Casual Encounters, I thought I’d share my very first CL success story.  In those days AFF, Craigslist and SLS were the only real means of finding a hookup online.

I realized that posting was really the best was to find someone to play with.  Single ladies, I don’t envy you. May your inbox RIP.  I posted my ad and within a few hours, I was chatting with Joyce.  She said she was older but played coy about her age for a while. She said she loved younger studs with stamina.  We flirted by IM and exchanged some pics. Before I knew it, she was inviting me over.  Nervous as fuck, I agreed and gave her my cell number.

Rachel [MF]: My Soul Mate

Rachel was the first real slut I’d ever encountered. She was my step sister’s best friend and was always at the house growing up. Rachel was the first girl I truly lusted after. I’ll never forget the first time she bent over in front of me; her red g-string riding her hips above her jeans. I was in love. Obligatory: Everyone is 18 in this story.

Naturally, I was friend-zoned because of her friendship with my sister.  It was agonizing to be near her through the times I was single and if I’m honest, the times I wasn’t either. We talked about everything, especially sex. She’d always tell me about who she fucked, where, when, the deets… Fuck, I wanted her. 

Her first 2 years of college were wild. Tons of booze, drugs and cock. So much that it landed her in jail, hospital and rehab on a few different occasions.  We reconnected after she moved back in with her parents during this rough patch.  I helped her find a job and told her she was welcome to come to my college house whenever. We’d always been close but things were different. We started hanging out and things got romantic. She’d always tell me about her wild fucks with random guys but never wanted to flippantly cross that line with me.  At the time, I was her rock. I smoked weed but kept no liquor in the house and was otherwise very anti drugs and party lifestyle . She needed to be away from the party life and sought regular refuge at my place.

Premeditated Infidelity [MF]

[Trigger Warning]: This post is about cheating. Please move along if you intend to spam me with hate or judgment. Save your breath, I know I’m scum. Thanks! Obligatory: Everyone is over 18.

 For a laundry list of reasons, I ignored my gut and decided to try monogamy once again. It all seemed so promising at first. She was fun and spontaneous with a great sense of adventure and a firecracker in bed to boot. Our sex life was intense from the very beginning. She was more open minded and comfortable with exploring new ways to enjoy each other’s bodies.

We built trust quickly. I knew that I needed to share my sexual history with her early to get a sense of long term potential together. I spent most of my 20’s single. I didn’t desire a commitment because I was still trying to figure myself out. I found myself gravitating towards Lifestyle sites and events. They fit with my ‘sexual ethics’; I didn’t want to play games, lead women on, date, break hearts… I just wanted to find women already on the same page: the intent is to meet for sex. If we click, let’s play again and often. Nothing else implied.

[MF] Busted in a car with a milf twice my age.

I’ve always had a thing for older women. Seeing Stiffler’s Mom on American Pie as a teenager and fantasizing about meeting my own version someday. I lost my virginity to a family friend and former babysitter that was 6 years my senior. But that’s a different story for another time. I want to tell you about Katie.

I was 19, heartbroken from getting dumped by  my high-school sweetheart after she told me she was fucking the guy down the hall in the dorms. Yeah, she dumped me… My self esteem wasn’t great back then. I was too raw for dating or anything relationship like; I devised a guilt free search for meaningless sex.  Long before tinder, Swinging and Adult Lifestyle websites were my best hope next to Craigslist.

One of my first replies was from the female half of a couple.  She said she was looking for a young guy, experience unimportant. We started chatting and I was so over-eager, I’m sure. She was a gorgeous blonde married milf of 2.  Her body was that of a real woman; curves, cute little love handles and a couple of stretch marks, battle scars from motherhood. She appeared confident and sexy in her photos and had a wonderful way with words. She was reassuring and kind as I nervously told her that I was new to the concept of casual sex. Our age difference intimidated me as much as it excited me. She was 41, 22 years older.

Exploring anal with cheating gf I met on AFF [MF]

I dont know about you all, but from time to time I shut off the porn and dig into the ol’ spank bank for some hot memory action.  Since I’m just barely on the otherside of divorce, you can imagine there’s been a bit of ‘me’ time.  There are my absolute favorites but every once in a while, I stumble into the memory of a long forgotton encounter.  I decided that I dont want to forget the hottest encounters with the women I’ve been with over the years.  I’ve posted a few stories with throwaways and one other account.  I’d just like to have all of them together from now on.  If you see a repost, there’s your disclaimer. Also everyone in the story is over 18 and names have been changed.

Like many guys growing up in the glorious age of internet porn, I always wanted to experience the feeling of a tight asshole gripping my cock.  I was told by my first few girlfriends that my size made it out of the question. I never considered myself huge by any means but Ive always known I’m above average in length but more notably girth.