High School Archives — Page 676 of 805 — NSFW story

The Capri Sun [MF]

Warning–this is long.

A few years ago, a friend and I went on a summer trip to Italy. We had not been romantic in any way prior to the trip. I had just gotten out of a toxic relationship, and the two of us simply meshed well. We were not close friends, and in fact did not know each other well at all. But Nicky’s youthful energy and enthusiasm for life and travel was just what I needed at a fairly dark time in my life, and without her presence in my life I likely would have spent a much longer time self-medicating with alcohol.

She had always wanted to visit Italy, and proposed just such a trip on a whim. It had been years since I’d taken any time off work so I agreed, and booked flights for us as well as lodging at the Capri Palace Hotel, an upscale resort on the island of Capri. Feeling caught up in Nicky’s enthusiasm for the trip, I reserved the Athena Suite, an exceptionally nice room with a private pool and garden. With that, Nicky took control of the trip planning, making reservations for meals and entertainment. Read more »

[FFM] Flirting to fucking in Room 403 (Part 1)

My husband and I make the trip every year to come home for the holidays, it is always a very hectic time of year. You have to make sure to do your rounds and see everyone or all hell breaks out.

So after a week of constant family, we needed a break from it all. Finally, on the last night we were in town, we got away for a night to ourselves.

We dressed nicely with me in a halter top and a skirt with slits up each thigh, and him dressed in a button down and slacks.

Once ready we headed out. We chose a small bar that had just about every beer you could want on tap. We opted to sit at the bar, you never know who you will get to meet or flirt with.

I was on my second beer when I felt someone behind me. Before I had a chance to look I was encircled in a tight hug. It was Ally, my best friend from high school.

“Oh my God. I didn’t know you guys were in town. How are you?” Read more »

Nothing is sacred [MF]

It was Christmas Day, and I was in high school. I had a long distance relationship with this girl Tina. The relationship was a bit strange, as many relationships in high school are, where I never really felt like I knew much about her. We chatted online. We talked on the phone. Didn’t matter. Without hanging out in her presence or with her friends, it was a different kind of relationship. I was the guy on the side, the x-factor, the unknown.

We had times when our relationship was incredibly sexually charged, and had times where it didn’t factor in. Sure, that’s how real life is sometimes, but like most teenage guys, my libido was often in overdrive. So much that I went out to visit Tina for Christmas.

Dinner was pretty boring. Her dad clearly didn’t trust me, and her mom wasn’t too fond of me either. They did their best to discourage anything from happening between us, and did a pretty good job for the most part. Needless to say, I walked around with an granite-like erection most of the time. If I were a teenage daughter’s father, I wouldn’t like that about me either. Read more »

An old friend of mine from high school [30F] coming to visit me[32m] [MF].

It all started back in high school, she used to date a friend of mine and I for whatever reason didn’t like her. one day we were all hanging out, she and I had a little time together to chat and found out she was actually a real person and fun to be around. Since then we have been good friends and with benefits.

She at some point broke it off with my friend and he moved away somewhere. for a couple of weeks she would seek me out and just chill with me, I would walk her home and shit like that. I wasn’t into her because at the time I didn’t know better and I totally judged her on being a bigger girl. Read more »

Crossdressing Teen with Step-Dad part II

This is a continuation of my previous story – link in comments.

A few months have passed since my first night with Chuck. Our relationship has noticeably improved, as my Mother has even made a comment or two. I’ve started my senior year in high school. Thanksgiving is soon around the corner. Chuck has become accustom to receiving blowjobs from me regularly. At least twice a week, he visits my room with a light knock on the door. One particular night was different though. He knocked and entered, presenting me with a gift. He set it on the bed and said he’d like to see it on me, he said he’d be back in a few minutes. Read more »

[mf] The dress

Hi! I’m back. I’m going to continue to post stories of my past to make me feel better about my super boring present!

When I was 20, I was a huge asshole. I still am – but I was then, too. I had a girlfriend named Kristy and she was everything a man could ever ask for. She was a bit shorter than me, probably 5’5″ or so, with brown hair and big brown eyes. In high school she was a gymnast – which has loads of benefits. When we started dating she went on birth control because she “loved how it felt when I came inside her”, and not only did that mean we could fuck without a condom, it also meant her boobs got bigger. So her body was like instagram-model absurd. She was a nurse (at 20, an RN) and had no problem paying for my meals. Maybe craziest of all, she loved fucking other girls in front of me. I should have married this woman. But alas, I was an asshole. Read more »

Crossdressing Teen with Step-Dad

I was an only child to a single mother for all of my life. Well, that was the case until my Mom started dating Chuck. I was fifteen when fourteen when Mom met Chuck and married him a year later. I wasn’t the typical “young man” and didn’t try to challenge Chuck, who was proud to assert his Alpha male status when Mother wasn’t paying attention. You could say Chuck and I never really got along, although I was glad he made my Mother happy.
Everything changed during the summer of my Junior year in high school. Chuck worked as a handy-man/contractor and owned his own house renovation business. That summer, everything to include myself thought it would be good idea for me to work with Chuck. This would give me some “bonding” time with a father figure and maybe learn some helpful skills for later in life. Not to mention the fact it would give me spending money. I’ve seen the worst of Chuck’s behavior, I’ve dealt with him for a couple years for free, at least this time I would be getting paid.
As anyone in the contactor business know, work isn’t always steady, as I soon found out. Chuck would tell me to take the day off because he couldn’t afford to pay me for the piddle job he had lined up for the day. With Mom at work and Chuck out the house, this gave me the perfect time to play dress up. I’d been crossdressing since I was eleven. For me it was fun and a great way to pass the time while doing some choirs. Read more »

[M]y first soft threesome with [M]y best friend and his new wi[F]e

A little background. I am 6 feet tall and a athletic build from playing a ton of soccer. Joe is about 5’9 from Thailand and really fit from doing a lot of martial arts. I met Joe when we were freshman in high school, I was new and we had a lot of the same classes and we quickly became friends. We hung out a lot and being teenagers our conversations always turned sexual. Whether we were discussing what girls we had crushes on to trying to figure out how different sex acts worked. I grew up in the age of dial up internet so answers were not as easily accessible as they are today. Shortly after high school we drifted a bit but one day he called me up to discuss his new wife. She was gorgeous and I’ll admit I was seriously jealous. She was about 5’2″ petite with freckles and bonds hair. (For those of you who need more of a picture think of the porn star Dakota Skye, with more freckles) After a bit of small talk he tells me that him and his wife Linda want to try some kinky things and he thinks a threesome is something I’d be up for. I must’ve asked 50 times if he was sure and he kept insisting they had talked about this for a while and it wasn’t just a spur of the moment thing but carefully thought out. We setup a time for them to come over to my house and after a bit of awkward small talk, we went over ground rules. Basically he didn’t want be to kiss her on the lips or have sex with her but anything with hands and oral was fair game. I was totally ok with that and understood my role here was to be an extra cock for her to play with while her husband fucked her. I took a passive role and followed their lead. This was everyone’s first threesome and I was afraid if I moved too quick I would spook them.
They started undressing and I followed making sure to mirror my friend Joe. Linda had stopped and sat back and watched us undress and admiring the view. Once we were down to just boxers (which was not doing anything to hide our excitement) she finished taking off her clothes. I could tell by the look in her eyes the extra attention was working for her. Once she was completely naked she laid back on the bed and started caressing her pussy with one hand while the other roamed up and down her body. I looked over at Joe who was smiling at me as if to say “yeah, I know. You’re welcome.” Linda directed us to pull off our boxers so she could finally get a good look. With all the anticipation and excitement I was already as hard as I could get. I look over at my buddy Joe and for the first time I see hesitation in his eyes. I’m not the longest guy, only about 7 inches, but I am very thick to where when I grab my dick my finger tips cannot touch. My buddy on the other hand is not as fortunate. His dick is nothing to be ashamed of but it was definitely smaller and I could see that he was having difficulty getting fully hard. Linda also notices so she crawls over and starts rubbing our cocks. First his then after a minute mine too, again I’m cool with this knowing I’m a supporting character for them. Joe is still struggling so she starts to suck his cock. Still no progress. I can see Joe getting more getting more frustrated and about to shut it down, so I tell them I’m going to go get some water and let them do their thing. I wasn’t going to get any but that doesn’t mean my buddy shouldn’t. They half protest as I walk out and go sit in my living room. About 10 minutes later Joe calls me back into the room, I figure they’re done. I walk in and he is in the middle of just railing her! I was relived my buddy could get it up again so I sit back in my desk chair and watch not wanting to disrupt his rhythm. After a minutes they move so she is on her back wth her head just hanging off the bed and she calls me over. I look to Joe for approval and he nods so I walk over. I was not hard anymore cuz I didn’t think it was gonna work out for me but she pulls me close and starts to gently kiss the tip of my cock and it jerks with excitement before she takes me into her mouth. I can feel myself getting harder inside her mouth and she is using Joe’s thrusting to suck me off. Joe says he is getting close to cumming but didn’t want it to end yet so he pulls out and we swap sides. I kneel between her legs and start teasing her with my tongue lightly licking her thighs and pubic bone. Anytime I get close to licking her pussy lips I stop and start over on the other side. I do this a few times and then I just barely touch her pussy with my tongue and she grabs my head and shoves my face deep into her pussy. My whole face is buried and I can’t really breathe but if this was how I died I was happy! She eventually let up and I was able to breathe again. Linda is sucking on Joe but stops long enough to tell me “I need you inside me!” It took every ounce of self control I had to not slide my dick inside her but those were the rules! I slid my two fingers inside her and went back to eating her out. Linda was absolutely loving everything we were doing to her. After a bit Joe says he’s ready to fuck her again so she complies and gets on all fours facing the side of the bed with me standing right in front of her. Joe starts off slow and Linda starts sucking my balls. I was decently experienced at this point but no one had ever sucked my balls before. It was amazing and now one of my favorite things! Joe’s pace starts to pick up so she moves back to wrapping her lips around my cock and letting her husband’s thrust dictate how far deep she went on me. It felt so good and Joe must’ve thought so too because soon after he pulled out and came on her asshole. Linda is able to steady herself more during my blowjob now that Joe wasn’t fucking her and Joe walked around and stood next to me to watch his wife suck my cock. Joe’s asks if I’m close and I tell him I am. I wasn’t, I just panicked because he had already finished and I wasn’t sure how much longer he’d let me throat fuck his wife if he wasn’t involved! He responds with “Good, I want you to cum allover my wife’s face.” I immediately lost it and started cumming rope after rope. It took us all by surprise how much cum I had and was shooting it all over his wife’s face. It was so dirty and so awesome. After I finished Linda licked the last drops of cum out of my dick and collapsed into a sex coma. Joe lays down next to her and I collapse into my desk chair.
After we regained our strength we cleaned up and jumped in a car and went to get something to eat. We finished up dinner and said goodbye talking about how this could be a regular thing. Unfortunately it wasn’t. I never knew exactly what happened but Joe and Linda split up later that year. Joe and I drifted again and even more so after I joined the military. After that I became something of a go to guy for threesomes and had several more since. It wasn’t the ending I really wanted but that was an incredible night.

[Mf] a day in the past (cheating)

This is my first post and I have been a lurker on here for awhile now but want to share a story about a time involving the girl I lost my virginity to. We were broken up for a few weeks and she already moved onto another guy she is married to right now. Here is a description of myself I am 5 foot 7 I have short dirty blonde hair, a red beard, wear glasses, skinny body and my dick is 6 inches exactly maybe a few centimeters more. The girls is about 5 foot 3 maybe 4 had b cup size boobs that were fucking fantastic to cup and grab, skinny body, about shoulder length brown hair and the second best pussy I have ever got to see, fuck, kiss and lick. So there is us, here is the sex story now for all of you people, we were texting back and forth and she said she wanted to hang out it was around 9 o’clock at night, i said why dont you just stay the night since there it was getting late. She said okay and was on her way. She text me im here so I go to the door and let her in. We start making out right in the door way till I lead her to my bedroom just down the hall. As soon as I closed the door she was all over me saying she still loved me and so me being the stupid guy I was back in my high school days I was like I love you too even tho I really wanted to have sex.
Sorry here is the sex part now
I push her up against the wall and started kissing her heavily and took off her shirt while she took mine off we kept making out and i slipped my hand down to feel her pussy wet and warm. I inserted 2 fingers and started going to town on her while she just breathed heavily in my ear while moaning yes taylor yes keep going!!! I nibbled on her ear for a second cause she loved when I did that and slowly worked my way down only stopping to suck and play with her nipples with my mouth and other hand. Before I get to her lovely beautiful pussy I bring over to my bed and take off her pants and underwear. She gets mine off as well and just gave me one of the best blow jobs ever. I turned it into 69 and just ate and fingered her while she tried to keep giving me head but she couldn’t finish it. I put her on her back and ask if she is ready and she said yes. I push into her and draw out doing long but slow pumps till she is moaning and saying it feels good right when she was getting close I flipped her over onto her stomach an put a pillow under her hips and started going to town on her switching from long and slow to fast and just half my dick in her. She told me to go faster cause she was getting close I started drilling her till she came. While she waa having her orgasm I kept pumping in her slowly and got her into doggy style. When she got calmed down I fucked her rough till I was a bout to cum and pulled out and came on her boobs and face. We fucked atless 6 times thru the whole night and in the morning.