Tag: High School

Journal #1: [MM] The time I (18M) got more than I bargained for with a random man (M30’s) from Craigslist personals. Long and hot story from when I was in college.

I have always been a very sexual person. Coming up, I had done a lot of solo sexual exploration, this led me to discovering tons of fantasies, fetishes and kinks in my head, but living at home, I never really had an outlet for them. Throughout high school I had the same girlfriend and we had a great sex life, basically humped like rabbits, but it was always pretty standard sex and at the time I was pretty ashamed of the abstract sexual thoughts I had concocted in my head and never broached the subject with her. One of the biggest ones was loving to wear women’s clothing, make up, shoes – which I later found was called Cross Dressing. For me Cross Dressing wasn’t really inherently sexual, but it was a way for me to transform from a boy to a girl, the thought of which just made me happy (more to come on this in another story).

Fast forward to college. I move into the dorms with my new roommate, who was openly gay, we’ll call him Dan. We were pretty close (just as friends) and soon made friends with several people from our floor, we’d all go out together, eat together, study together you name it, we were close. Read more »

[MFF] They called it “Torture Time”, it was anything but torture

I was so inexperienced at the time that the thought of being with two girls at once had never even crossed my mind. It was the early 90s and a much more innocent time before the invention internet porn. I was still jerking off to the lingerie catalog from Sears or a playboy when I was lucky enough to get my hands on one. I was so happy one girl was willing to have sex with me and I wasn’t sure anyone else ever would again.

It was the summer after we graduated high school and my girlfriend Emma (name changed) had decided to take our relationship to the next level and we had sex for the first time the night after graduation and the following weeks consisted of having sex all day while her parents were at work. It was that exciting kind of sex where everything is new and awkward. You’re exploring and learning and you never really get to have that feeling again. All these years later I still look back on that fondly. Read more »

Red lingerie unleashes something in me [Mf]

So I’m male and a senior in college, this happened last year with my now girlfriend. The girl in question, let’s call her Rachel, is about 5’10, has dark brown hair going down to the bottom of her shoulder blades, dark amber eyes, perky C cup breasts, and a round ass that will be etched into my brain for the rest of my life.

Backstory:

Rachel and I had gone to the same high school, we knew of each other but never really talked until our junior year music theory class. She’s a theater girl and a hell of a singer, I’m a tenor saxophonist trying to make it seem like I know what I’m doing.

Anyway, it’s a really small class so we all get to know each other pretty quickly. Rachel and I actually hit it off but it’s another month and one obvious hand on my leg for me to ask her out.

We go on a few dates and while it wasn’t exactly a Hollywood movie, we had a good time and had done some minor make out stuff, though nothing sexual yet. Read more »

[MF] The first time I [M20] took my now-wife [F19] home to my parents

Despite the fact that I practically moved in with Laura and her family shortly after we started dating, my parents didn’t meet her until almost a year and a half after we started dating. Part of this was due to the fact that she lived at home near our college, and I lived hundreds of miles away in a different state. However, another reason for this was how my parents treated relationships. Those of you who have Middle Eastern parents most likely understand how careful you have to be when you date someone. If you’ve been dating them for more than a few months, you better be prepared for a serious, long-term relationship. It’s leaves you in an awkward situation where you have to either be treated like a married couple, or just not tell your parents about your relationship. Read more »

Dude…you gotta fuck my wife with that thing

I never thought I’d hear those words come from my best friend’s mouth, but one day in the locker room, I had to make sure I heard what I thought I did. “What did you just say?” I asked with confusion written all over my face. “Dude…you gotta fuck my wife with that massive dick.” Now, we’ve seen each other naked plenty of times, so this caught me off guard. I looked him on the eye and asked…”Why?” He just looked right back and said “c’mon bro. She’s been dying to get pounded by a huge cock since high school. You know this. I don’t get why you never even tried!” I shake my head before responding. “Dude, she’s been your girl since 8th grade! You’ve been my best friend since kindergarten! Not gonna fuck that up for some pussy.” He laughs at this. I stare blankly as he takes another look at my dick. “Dude how have I never noticed how huge that dick is? We practically grew up together and it’s not like we’ve never seen each other naked.” I’m still looking at him in confusion. “Didn’t realize you were so into big dicks, man.” He laughs at me again. My cock twitches a little from all the attention though. I try my best not to get hard. He doesn’t need to know how big it gets. “Seriously, you gotta show it to my wife. She’ll be all over that beast.” I don’t know, I really don’t want to jeopardize our friendship. His wife is hot, I’ve known her for years. I start imagining her curvy body naked. Big mistake. “Fuck, bro! How big does it get? You picturing my wife naked now? I promise you she looks even better than in your imagination.” I know she has an incredible body. I’ve seen her in bikinis plenty of times. She doesn’t leave much to imagine. I’m rock hard at this point. “Dude, come over tonight. Wear gym shorts with no underwear. I’ll take care of the rest.” I sigh and nod. “Awesome! She’s gonna fucking love your mobster, bro. I should warn you, though. She loves to suck cock, and you may need to pry her off of it to fuck her. See you tonight!” He gets dressed and excitedly heads out of the locker room, taking one last glance at my now throbbing erection with a smirk. He knows I’m hooked on the idea. I rub one out in the shower to relieve the pressure, and make sure I don’t cum too soon tonight. I know she’s gonna be super tight. I love my buddy like a brother, but let’s be honest. He’s way smaller than me.
I stop at my apartment and try to calm my nerves before heading over for dinner at his house. I put on my most flattering gym shorts, with no underwear as requested. Read more »

A New Sensation with the Bella Twins [WWE] [Feminization]

It was late in Omaha and the hotel lobby was so quiet you could hear a pin drop. There was no sign of any other humans, but that was typical of most Monday nights. There had been a little bit of ruckus earlier in the night. There was a WWE show at the Civic Center close to the hotel and that always brings a certain element of drunken idiots through the hotel. The hotel bar was packed with people trying to keep their buzz going after the show, but thankfully they were all gone a few hours after I started my shift. It was the time of night that I longed for every shift, a time where I could just space out and think. Read more »

Adventures in Broadcasting, pt 10: the Gift

Her name is Y. She was always early. She’d always show up when we had about an hour to go, even though she didn’t go on until noon. She was T’s best friend at the station, but I don’t know if Y was aware of T’s personal life. Every morning I’d catch T and Y chattering although I could never hear what they were talking about. Inevitably, one of them would say something and they’d both giggle like schoolgirls.

So on the day of my promotion, I left the station manager’s office to find the whole cast and crew (except for C, of course) was there to meet me for a surprise congratulatory celebration. As I made my way through the throng of well-wishers, T came up and whispered in my ear, “I got you a surprise. I can’t tell you about it now, but you’ll know it when you get it.” I didn’t know what she meant by that, but the mysteriousness gave me a semi. Knowing T like I did, it had to be good. Read more »

Mom and Son – Mom teaches Son about sex.

I was lying in bed watching my beautiful wife prepare for bed. She had just stepped out of the shower. I was admiring the beauty of her nakedness as I could easily watch her toweling off. Her breasts were medium size with a firmness that allowed her nipples to point forward. Her torso was very shapely with a narrow waist line. After giving birth to our son, she had exercised to restore her original curves. I could see the slight crease of her shaved pussy while she was in the standing position. Her long slender legs always looked so sexy when wearing a dress. Now I could see the full length from her toes to her crotch. I looked up to see her face. Her lips looked so desirable to be kissed. Her long blond hair flowed down the sides of her face and back. I’m so lucky to have her as my wife. She will soon be in bed with me. 

While watching her, I started to reminisce. When I was a boy growing up with my mom and dad, I was very curious to see what a girl looked like without any clothes. I didn’t have a sister to peek at. But, I was always tempted to catch a glimpse of mom.  Read more »

Forbidden Lust – Getting Caught Masturbating Leads to Oral Sex [caught][MF][panties][school girl][18 years old][tease][sneaking]

I woke up on Christmas Eve to the sound of someone knocking on the door. It was after nine o’clock. I was asleep in a guest room in my uncle’s basement. Next to me was a pair of my panties that were stiff with my dried cum. Cara had used them the night before to give me a handjob while everyone else in the house was asleep. It was the third time in less than a week. The first time was right after she caught me jacking off in her basement.

At first, I felt guilty. Cara was only eighteen years old. She was still in high school. And she was my aunt’s step-daughter. We weren’t blood-relatives, but it was still an unusual situation. I’d known her since she was in elementary school. Our family thought it was cute that she had a crush on me growing up, but an actual relationship would have been scandalous.

But the guilt faded quickly. It was replaced with desire. The taboo element to our secret encounters made them more thrilling. I was becoming obsessed. Read more »

Fourth of July Makeout [FF]

A couple years ago during the summer between my freshman and sophomore year I went to a Fourth of July party with my then boyfriend and all of our friends from high school. During the day, my boyfriend’s friend, we will call him Joe, brought his girlfriend Amelia with him to the party.

As we were drinking and goofing around on the porch, she and I began to flirt, and at one point, I had this tiny, 5’2, 95 pound beauty sitting on my lap leaning into me, in front of our boyfriends. Both of them were laughing, and I saw a look exchanged between the two, noting that they liked it. So, I continued to wrap my arms around her and pull her closer, she seemed to like it, and through the day into the evening, she and I would casually flirt and make jokes at our boyfriends.

Once the half-hour show was completed and the adults had left, leaving the college kids alone at the bonfire and with all of the drinks, we all had fun. One friend insisted we play truth or dare or drink, and at one point, I was dared to give Amelia a lap dance. It was awkward and not the best, but you could tell that all of the guys present were watching and enjoying the show. The game continued on until we all decided we were ready to sleep off the rest of the night. Read more »