[M]y Virgin Experience Fingering a Close [F]riend and Later Getting a Blowjob in College

This might be a tame story compared to people who actually have sex in their stories, but I was raised in a female household and pretty much didn’t want random hookups in college but didn’t have looks, time, or money for a girlfriend. This is the story of how a nerdy guy got to finger a friend from freshmen year of college and eventually get her to give him a blowjob. (I fingered her jr year, but the blowjob won’t come till senior year, so this is a two act story.)

Part 1: The Fingering and Foreplay

Gf’s first threesome [MFM]

My gf Elle and I (both 24) have had a bit of experience in sharing her. She has fucked a couple of other guys with my knowledge and encouragement, during a period where we were doing long distance. The texting and snapchats leading up to and during the hook ups were super hot and intense. She recorded a couple of videos to send to me in the aftermath, and we both found it really hot. We both were interested in trying out a threesome, and this is the story of how our first one came to be..

We were travelling together through south east asia, just the two of us. Many of our nights were spent drinking and partying, meeting fellow travellers and having a good time. Elle liked to flirt with guys that she liked, and often dirty danced in front of me. She’s a tease. Until one night, on a certain party island in Thailand, she decided it was gonna happen. I was gonna see her get fucked. Elle downloaded tinder and, as we expected, many options soon presented themselves. Elle took a liking to a good looking and seemingly charming guy, who we’ll call Alex. They got to chatting, and sure enough he was staying at a hostel just a short scooter ride away. Elle explained the situation, and Alex was happy to oblige. We arranged to meet him at our hostel bar later on that night for a few drinks. We settled down at the pool to get a few vodkas into us and prepare for the night to come.

I Cheated With The Babysitter {PART 4} [Str8] [M/f] [Teen] [Age Gap] [Cheating] [Rough] [Oral][Creampie] [Daddy Kink] [Schoolgirl]

**I STRONGLY suggest that you read the previous installments if you haven’t already.**

A link to them can be found in the comments below.

**POSSIBLE TRIGGER WARNING**

*This chapter features themes that some people may find unsettling, uncomfortable and/or troubling.*

***Reader discretion is advised***

# Author’s Note and Further Trigger Warning:

>*Hi all! So I don’t want to spoil too much but just to be completely safe as to not make anyone feel uncomfortable, I want to clarify something about this chapter. Part four contains a roleplay between an eighteen year old girl and a middle aged man. The roleplay sees Kimmi act as an innocent schoolgirl whilst both of the characters refer to Mr S as ‘Daddy’. This of course means there’s a hint of incest included. (I say hint as the term daddy is often used for reasons unrelated to incest but given the context of the scene, it will likely feel more . . . incesty?) There’s no intended ageplay here but the inclusion of an* ***innocent*** *schoolgirl could certainly be interpreted that way. Finally, there’s a bit of rough sex in this chapter with hints of forced sex, particularly with one line from the main character. However, there is zero non-consensual sex in this chapter but as I’d truly hate to upset anybody I just wanted to post an adequate warning. Otherwise, enjoy the story! As always, I’d love any feedback/comments so please let me know what you think. I’d also like to let you know that I will be ending this series soon but I have tons of other kinky and erotic story ideas for the future so I hope you’ll explore them with me.*
*With love,*
*Indigo.*

I Cheated With The Babysitter {PART 4} [Str8] [M/f] [Teen] [Age Gap] [Cheating] [Rough] [Oral][Creampie] [Daddy Kink] [Schoolgirl]

**I STRONGLY suggest that you read the previous installments if you haven’t already.**

[PART ONE](https://www.reddit.com/r/sexstories/comments/7vacjg/i_cheated_with_the_babysitter_str8_mf_cheating/?st=jl143ca9&sh=afb242cb)

[PART TWO](https://www.reddit.com/r/sexstories/comments/8mus2s/i_cheated_with_the_babysitter_part_2_str8_mf_teen/?st=jl5qfaqi&sh=3b92e5a1)

[PART THREE](https://new.reddit.com/r/sexstories/comments/98d9nj/i_cheated_with_the_babysitter_part_3_str8_mf_teen/)

**POSSIBLE TRIGGER WARNING**

*This chapter features themes that some people may find unsettling, uncomfortable and/or troubling.*

***Reader discretion is advised***

# Author’s Note and Further Trigger Warning:

>*Hi all! So I don’t want to spoil too much but just to be completely safe as to not make anyone feel uncomfortable, I want to clarify something about this chapter. Part four contains a roleplay between an eighteen year old girl and a middle aged man. The roleplay sees Kimmi act as an innocent schoolgirl whilst both of the characters refer to Mr S as ‘Daddy’. This of course means there’s a hint of incest included. (I say hint as the term daddy is often used for reasons unrelated to incest but given the context of the scene, it will likely feel more . . . incesty?) There’s no intended ageplay here but the inclusion of an* ***innocent****schoolgirl could certainly be interpreted that way. Finally, there’s a bit of rough sex in this chapter with hints of forced sex, particularly with one line from the main character. However, there is zero non-consensual sex in this chapter but as I’d truly hate to upset anybody I just wanted to post an adequate warning. Otherwise, enjoy the story! As always, I’d love any feedback/comments so please let me know what you think. I’d also like to let you know that I will be ending this series soon but I have tons of other kinky and erotic story ideas for the future so I hope you’ll explore them with me.*
*With love,*
*Indigo.*

Young Love (Part 1.)[Str8][Fm][slowbuild][nosex][mast]

*continued in comments*

The shrill sound of a ringing bell cut through the lazy summer air, startling two squirrels, who scampered along the grass until they reached a tree. They were already taking refuge within the leaves by the time the front doors to Edison High were thrown open.

Students started spilling out onto the front steps, carrying backpacks, binders, and sporty duffel bags. The sound of excited chatter filled the air and a football soared over the crowd. Inside the building was even more hectic, with people shouting over each other or running to tell their friends the latest gossip.

Anthony tugged open his locker. It got jammed sometimes, so it often helped to give it a good yank. It gave and swung open, and his hand paused over a folder labeled “Music.” He stared at the folder, deep in thought as his finger traced the edge. His ex-girlfriends hysterical voice rang in his ears and he recalled the sight of her tear-streaked face.

*”You like her?! Answer me! Do you go over to her house so she can teach you how to fuck? Do you want her to be your **sex** teacher?* *Huh Anthony?! Is **she** what you want?!”*

I was a horny,methamphetamine fueled teenage,masturbation machine!The crack of dawn made me horny!(masturbation,drugs,solo,mm,m older f,incest)

The summer I graduated was my second,but first big sexual awakening.I was somewhat of a late bloomer when it came to puberty,having been pushed through with steroids,due to allergy issues,however they seemed to speed me through it very rapidly,full force.As a result I was very muscular and very horny ,however it left me with a slightly smaller than average package… of dynamite!.I was an advanced student throughout school ,which meant I was usually a couple years younger than my friends and classmates,and also a year to kill between high school and my planned college education.Well when my father died I was only 15 and my mom moved us from the Adirondacks mountains of upstate New York back to Northern California.With mom working quite a bit and enjoying her new found freedom I was free to get into whatever mischief I felt like and oh did I.I immediately grew my hair long and started experimenting with drugs,favoring coke,but meth was cheaper,easier and everywhere,literally,walking down the street complete strangers would ask,”hey,wanna do a line”,it was the mid ’80’s.This wonderful drug kept me at a constant full sexual lust,but further shrunk my little,horny,cum leaking package. ……..It was summer 1987.I had just graduated,a year ahead of most of my friends(I had been advanced a total of 2 1/2 years throughout my school years)I had at least a full year to fuck around before my serious education started.I worked some construction with my older brothers so I had cash,a new truck,a steady girlfriend that I ditched at least three or four days(and nights)a week to party.Oh, and I sold some screaming good speed on the side.After a night of hopping from kegged to kegger it was about 2 am,it was hot,june in Northern California,my buddies and I decided that since we where all wired for sound and we’re gonna be that way for a long time cause the shit was so good back then,we would grab our fishing poles and reconvene at a spot on the river where we often had bonfires and small parties,kinda hard to drive to without a 4wheel drive but close by.I was hiding from my big boobed,big sexy fat assed,bon Jovi bitch girlfriend so I hitched a ride with my buddies even sexier much older sister as she was going home right passed the dirt road down which our little beach was.I chopped her and I a ridiculously large line up(hoping she would wanna take me home to fuck,but struck out)and walked down to the river a couple of trucks were already there so i lit a fire and baited my hook and drank beer and bullshit with a dork till my buddies showed up shortly thereafter.they threw a hook in and grabbed a beer and picked on the dorks till they left.We were babbling on in meth fueled talk till the sun started coming up like my precum leaking crankdick when they announced that two of them had to go,as they had to start a new job harvesting prunes that morning,one other wanted to go home because he didn’t catch anything and was cold and mosquito bitten.I said I was gonna stay because I had caught a couple of decent fish and I could walk the 3/4 mile home.We agreed to meet that same evening when the others got off work to fish some more.One of the boys handed me the paper bag with the bait and three or four porno magazines he had shoplifted while buying bait the night before,he said oh,”here in case you get bored or horny”,have’nt even open ’em yet,they are virgin,no stuck pages”,I called him “fag”,and they left.leaving me,the fire,fishing pole,couple beers,a water…..and entertainment. After the sun rose it started getting hot,fire died,I chopped another bagger and got up to piss and check on my drooling amphetamine shrunk-to-nothing sized little cock.It was so horny and shrunken due to how horny and wired I was that I could barely hold it so I dropped my shorts all the way down to the ground and dribbled piss and precum while bathing in the warm morning sunlight.Then….I remembered the porn mags that were left.Sweet!”I hope they are good and nasty” I said out loud,loving to talk dirty to myself like I often did when all tweaked and horny. I ripped the plastic open,wnile my shorts were still down at my feet.I kicked them off and sat on the large fallen tree that previously served as firewood and bench.In my hand was the Holy Grail of porno filth!Hustler,the most reliable publication of jizz flying scripture I had known,”WOW,its even current!”Beaver hunt and all,no missing pages or cut out IPC code,the FDIC of spankbanks!Also was a copy of Big Buttsex loving Mature sluts,or something like that ,also just what I was into….oh, and New friends swingers.As morning burned away I studied each page with the intense scrutiny of a chess player,while slowly,with two fingers,tugged and pulled at my shrivelled,pre-cum covered speed-weenie in the open.Occasionally taking a break to do another blast on a nasty page and licking the residue off some open asshole shot or tranny phone sex ad.I remembered I had a small jar of Vaseline I had taken from my friends sexy slut sister on the ride here(it’s still my favorite jerkin lube,first introduced by one of my jerking/cocksucking/buttfucking cousins a few years previous).The mere thought of having a jar of a females “pussy in a jar”made me squirt a little cum when I reached down to grab it and my asshole spread open so I felt a cool breeze inside it.I started to get MUCH hornier,thinking I would like to even have a guy there getting kinky with me or a boy. The Beaver hunt was great that issue,Kinky,nasty,perverted everyday sluts saying filthy,trashy shit like how they like to tease the neighbor boys by bending over dramatically show the cum in their freshly fucked assholes and great stuff like that.I studied each nasty dream mom or aunt and greased up my now hardening cock,occasionally slipping a grease covered finger to my horny asshole,then in it.All the sudden I hear something walking the the undergrowth and trees.I grab my Vaseline and forgetting about my sand covered shorts I creep back into the trees and on a trail about fifty feet away are some younger kids a fat,bully looking kid and two boys and a chubby girl all around the same age but the bully looking one he was maybe a couple years older.they don’t notice me and walk down the trail towards,i assume a shallower beach thats down that direction.I notice one of the other boys squats,moves a board and grabs something in one of those liquor store type bags and they keep going as I see the bully trying to,unsuccesfully”pants” both boys and the girl who is wearing a dirty one piece with tshirt. I take a skinny-dip to freshen up and revive only to have it once more shrink me to kid size,but clean and cool.I have come to be aroused and mentally like the idea of my horny little baby crankdick and imagine sucking one like it or getting buttfucking by one like it,in fact I feel kinda bold and proud,after all I’m pretty much built like a bodybuilder already,good tan,drug dealer,some sluts would still want to have nasty sex and play with my horny little blue headed cock! While getting back to stroking and studying each Beaver hunt,open pussy pic and statement,i am pleasantly aroused by not one ,but two of my hometown horny girls.One is this kinda strange dressing,older very eccentric lady that lived two blocks from my house!There was a neighborhood rumor that she sunbathed nude that was confirmed by her list of hobbies,next to getting men and boys to masturbate to her while she gives her pussy till squirting….then the last kinda beat up looking bottle blond,crankwhore that happened to be staying at my house temporarily while getting on her feet(..and attempting to catch one of my older brothers that was getting divorced and once in a while stayed at our house when not working out of town).This gal oozed the”horny,crankwhore” look,catching my eye upon introduction,prompting me to not only vote “yes” when asked whether we let her stay a few weeks or not,but I immediately locked myself in my room for a three hour five gunshot,stroke session,imaging her wanting to do vile nasty things for some of my dope. Then I hear some noise coming down river,its a group of tubers loudly talking about how someone’s tube popped and they were on foot.after they passed I openly sat on the bank,fishing and jerking my semi-hard cock with Vaseline,when out of nowhere behind me I hear a whistle,its a naked 25-30ish big guy with his cock rock hard jerking it all dry and red watching me.He is about twenty feet away,sunburned but his cock is easily three times the size of mine,although he is barely bigger in stature and I a much more lean and muscular.His hair is short and black too much body hair too.Im not sure what to do but I’m getting harder so I improve his view by turning around on this fallen tree I’m was standing on,jump to the ground bend over to grab my dropped Vaseline jar,while allowing my hairless ass to speed more than is natural,offering him some.”Looks like your getting red”.is all I can think to say,reffering to his dry stroked hairy cock.”yeah,i burn easy”he says thinking I’m talking about his sunburn.”There is some skinny dipping boys and naked fat girl upstream she is letting a kid fuck her while a chubby oversized ,bigger kid is giving head to another boy while he jacks off”,”they with you?””Nope not with me,i seen them go that way though””felt kinda creepy watching them,but it sure got me hard and thinking nasty””You OK if I lube up some more and Jack off with you,i could suck your cock or I’ll fuck you if you want””No, I’m good on that I’ve got some porn mags we can jack off together though””sounds good,you gonna be a bodybuilder?,”maybe”,”should,gotta good start”,thanks”. We flipped pages and stroked talking dirty,him saying how the older lady,he had seen around,thats when I asked if he recognized Peggy the tweeter whore staying at my house he said no but”where you live?”,I lied I speed my asscheeks and tried to open myasshole to help him cum,but he shot his wad on a tranny ad in the back of my magazine and left,,,I never did come…till that night when I came home,horny and sunburned to a crisp.Peggy was the only one there she was in lingerie my brother had stopped by,rudely told her “NoWay”,and while she was sitting in my room on my bed w with he r naked shaved pussy on my pillow trying to scrape a little mirror I had in my nightstand with my Vaseline….and the rest later…

That 5th shot of Patron and sex with a stranger [MF]

*If you have not read my previous stories.. you should know, my stories are VERY LONG. If you have read them.. you know this one won’t be any different. This takes place a month before my college graduation, and it is the story of the last time I hooked up with someone else who isn’t my current fiancé. Six weeks later, we officially began dating (and yes, we had hooked up before this and do afterwards but before dating) .*

**Backstory:**

[MMF] The year two of my roommates didn’t pay rent, Part 1

In my college days, I was something of a libertine among libertines. I ran with a theater type crowd at my school, a mix of unique personalities, but with one thing largely in common – we were all horny motherfuckers.

Starting the summer of my senior year, my friend Mark and I rented a two bedroom house off-campus to live in. It was a great deal – more than spacious enough for two and great for parties. We threw two or three parties every week, and had an absolute ball.

During the summer, my friend Sasha told me her parents had kicked her out after they found out she was smoking pot. She asked if she could crash on the couch for a few weeks, and I said sure. We’d always gotten along great, so I figured it’d be no problem.

She was a busty brunette with a big butt and a slim waist who had gone from pudgy-hot a few years back when I’d first met her to hourglass-smokinghot by the time she moved in that summer.

My [f]irst lesbian experience with a [f]riend/teammate

A little backstory first is important. I am starting my sophomore year of college and I am on the dance team at this college, same with my friend who I experienced this with (We will call her Nikki). I am 18 and turn 19 in about a week, she turned 19 months ago, but we’re both sophomores. She and I are actually similar in a lot of ways, both sophomores, both blondes, both came into college with boyfriends (although they did not last), and similar body types. The only difference is, on the dance team she is known for her rather large breasts while I am known for my big butt. When she and I get drunk we usually end up dancing on each other and sometimes making out, but nothing more than that.

Anyways, we had to move onto campus early because of practices starting, I moved in first with my roommate and the next day Nikki moved into her apartment a few floors down. My roommate and I helped Nikki move into her apartment, which went rather quickly, and my roommate went back to our apartment. I stay to talk to Nikki and we talk about classes, dance, her ex, and eventually my boyfriend. The year before I may have mentioned that I like to dress up and role play during sex (I was drinking), and so she asked me about that and said she had wanted to try it out with her boyfriend but he was a little skittish and they never did.

[MF] Military Academy Handjob with a Little Cleanup

I apologize for this being a long story. There’s not much actual sex in it, but it’s an (I hope) interesting look into what it was like in a slightly different environment than most people are subject to. There’s a short tl;dr at the end, so if you want a synopsis scroll way way down. The title is the real tl;dr though.

A long time ago in an America far far away, I was a West Point cadet. The only real reason that’s relevant is that sex was pretty much prohibited. Even getting caught jacking off could get you a big round of punishment tours- which you had to “walk off” by marching back and forth in Dress Gray “under arms” (i.e. with your rifle on your shoulder.)

As luck would have it, both I and the female cadet who was my first serious girlfriend were virgins when we entered the Academy. This wasn’t all that uncommon, actually. The type of person who gets into West Point has put an extraordinary amount of effort into their academic, athletic, and extra-curricular high school career. When you’re trying to maintain a 4.0+ GPA, be the captain of the lacrosse team, get your Eagle Scout rank, and serve on student body leadership, there’s not a lot of time leftover for girlfriends or boyfriends.