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
I met my friend Raven(alias of course) from freshmen orientation, but it was completely platonic up until junior year. She’s about my height, 5’5, latina, pixie cut hair, and curvy with what she later told me were 32C breasts. Sometime in junior year we started talking about sex and she told me how she hooked up with a friend in freshmen year to lose her virginity. Even though that could’ve been me, I was still holding out on having sex with someone I had romantic interest in. This got me to see her in a new light though and I started masturbating to her of course. And of course as a single young 20 year old I was very horny from time to time, so I submitted to my urges one night when my roommate was out to dinner on a Friday night. I invited Raven over to chill after a dinner with her, and we went to my room. At this point we talked about sex a lot, or at least I asked her a lot of questions about sex and she was totally chill with answering them honestly. At this time, I just wanted to cop a feel of her plump tits, and I knew she was very open about sex so I figured she wouldn’t be mad if I asked later (guys, do NOT do this with girls you are friends with IF you think they will be mad at you. Don’t jeopardize friendships because you need to jerk off). So I grabbed my laptop, showed her reddit, showed her GW and asked her if she was into exhibitionalism. She said no, and at this point I asked what porn she watched. She was really embarrassed and just told me she was really into BDSM but didn’t let up on any specific websites or videos. We kinda just sat there for a second as I closed the porn tabs, and before I could let the awkward silence blossom, I spoke out.
“Hey Raven? Can I ask you something?””What’s up?””So like in highschool I knew a guy who told me his friend let him feel her up for a little bit, and I was wondering if you’d let me do the same? I’d really like to touch your boobs.”
She gave a slight smirk but was really quiet.
“Is that a no?” I asked with a throbbing heart. I’ve never felt boobs before and hers were so tempting.
“Im thinking” she says. Before my heartbeat can slow down she says “Okay. Just over the clothes though. And close the door”
I sprint to the door and lock it. I come back and she says she doesn’t want me to see them directly, so I sit down and she sits down on my lap with her back facing towards me. I quickly spread my palms and get a handful of firm squishy bra. All i can say is “Wow.” At this point we both start breathing heavily as I continue to just feel her bra.
“Hey can I touch them.. directly?”
She’s quietly thinking for a brief period. “Okay.” I wanted to practice taking off her bra, so I say “Wait, Let me do it.” With one hand and a general understanding of clasps, I got them free. Oh fuck, I can’t believe this is happening. I grab her warm firm tits and slowly make my way towards her nipples. She lets out a soft moan as I tease her and get them rock hard.
“Hey.. do you think you can teach me more?” I asked.
“Depends. What do you want to learn? You don’t want to have sex right?””Can I touch you.. down there?”
She unbuttons her shorts and before she can even move her hand I slide my hand down and above her panties.”Whoa, its so warm””Yeah.. if you go lower, theres the entrance”I slide a little lower and feel her moist panties. Oh fuck shes so wet. Without even asking, I bypass the panties and go straight for her wet pussy. Oh fuckkk. She lets out a very deep breath and I’m the hardest i’ve been since I discovered masturbation.
“Wheres the clit?”
“A little higher.” I feel around for a bud of flesh, and the moment I touch it she moans in intense pleasure. In me is the intense drive to pleasure her even more, and my arrogance to make her cum. I slowly take my index and middle fingers and slide down to feel her slit. When i reach the entrance it is sopping wet and I make my way inside with my fingers. The moment I pushed in I felt resistance from her pelvic bone as she moaned even louder than before. (Although my personal roommate was gone, it was a 2 bedroom apartment and there was our 3rd roommate playing Dota with his headset on).
“You should stay quiet.. There’s someone else home and the walls are thin.. and I don’t want to be explaining this to him later..” (None of us brought girls over, we were all pretty conservative guys).
“Okay” she said,through her heavy breathing, as her pussy clamped down on my fingers. There was just enough space for me to press against her walls but not enough for a third finger. Using what i learned off the internet, I use the “come hither” gesture and this fucking gets her.
Somehow one of us suggests to lie down. I turn down the lights because she still doesn’t want me to see her tits, but that’s fine. Right now I just want to pleasure my friend. Now I’m lying directly on top of her, her shorts off, panties down but still around her legs, and I’m still popping a major erection. I can feel the precum just dripping onto my boxers, so I alleviate this by grinding on her leg.
“Hey you can take off your pants too, if you want” she suggested. “No.. that might take things too far” I backed out. “Okay” she says. “But you can at least put your entire body weight on me.”
I don’t know how I was able to keep any control in this situation, grinding on her sure helped, but I hadn’t even had my first kiss yet and here I am finger banging a friend. With my right hand I’m stimulating her clit like its some kind of joystick in a quick time event, and with my left im either covering her mouth of loud moans or playing with her nice breasts. This goes on for about five or ten minutes, before she says she needs to catch her breath.
“Wow. I didn’t know you had that much dexterity with your fingers”
“Yeah… video games.. haha””Wellllll, I can help you out too if you want””I really dont know…..””Okay””Ready to continue?””Yeah”
We get back to it, me pressing my weight against her as she grasps the back of my head with her hands and moans as silently as possible. I start kissing her neck and biting her ear when she lets out an audible “Ahhhh.” Before any more of this can continue, I hear my roommate come home from dinner. I rush to our bathroom sink to wash my hands and she runs to the actual bathroom to wiper herself off and pull up our pants. He opens the door to see her run to the bathroom with her pants around her legs, and goes “Oh ooops my bad.” “No problem man, how was your night?” “I;ll talk to you outside ha ha..” “Yea okay”
And myself and Raven exit the room trying to act composed, we put on a movie and later I drive her home with my roommate. He did ask me what happened later on, I lied and said that we slept on my bed, it got hot, she took off her pants, and ran to pee later on. “Nothing happened” Not sure if he believed me or not, but he knew she was a friend of mine since freshman year and he never brought it up again since she never came over again. And that was my first time dealing with foreplay.
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Part 2: The Blowjob
So here’s the blowjob story, it takes place in my senior year. Raven is working as a volunteer for student health this week and is giving out free condoms. Shes also in a fwb with someone and he’s supposed to visit her for the three day weekend. I ask her for some free condoms because hey, anything can happen and I dont know when I’ll meet a girl i like. So on a friday I bus to school for a comedy night, and head to her apartment on campus to grab the condoms. To make sure I dont do anything stupid, I jack off before I went to school (but the brain in my penis is stronger than I thought). I should also mention that she had her nipples pierced recently, and Ive been dying to see them (and saying “I dont believe you” doesnt work)
I go to her apartment and see what she’s up to. She’s doing homework and tells me she’s upset that her fwb cancelled on her. This immediately sends signals to my dick, but I try to convince her to go to the comedy show with me. She’s not really interested, but I dont really want to go by myself so I just stay in her room shooting the breeze.
“Hey so.. if you’re horny and your hookup is gone for the weekend.. Maybe I can help you out like last time?” So much for jacking off before coming here right?
“Thanks but no thanks” Shot down just like that.
“Wait.. why not? You had fun, I had fun, you’re not seeing him seriously”
“Wellll, we’re not going to have sex and I dont want to take advantage of you”
“What do you mean”
“Dude, I have a backpack full of condoms”
“Its okay, I have the willpower to draw the line, We can stop before it goes too far. So how about it?”
“Umm Im thinking”
“So thats a no then”
“How about you beg a little more” she says with a coy tone and a slight smirk.
“Please Raven. I really want to finger you again.”
“Fine. But lets lay down some ground rules. No lights. No sex”
“Okay, how much time do you want? 20 minutes?”
“No.. 20 minutes seems a little rude, How about 45?”
In my mind 45 minutes was a little long. I wasnt sure how long the busses ran and I didnt want to sleep over at her place. Its not personal, I just like my own bed.
“Okay.. lets set an alarm then? Oh and one more thing, Ive lost my first kiss, and I was wondering if I could practice making out with you?”
“Ummm I dont really like to kiss or makeout, we’ll see. Also I had my nipples pierced so, I dont want to show them to you sorry, only to special people. ”
My heart is pounding as she sets the timer. Fuckkk I cant believe this is happening AGAIN. Ive wanted to touch that magnificent pussy for a looong time, but she was really quick to jump into relationships with other guys.
She turns off the lights, lights some scented candle in the corner of the room, and I immediately pounce her and start kissing her. Im trying to get some tongue play but she isnt playing along, so I move on to her neck and her ears. I know how much she loved it last time. She’s enjoying this, and I start groping her through her shirt. “Wait” she says. “Let me just take off all my clothes, itll be more comfortable that way” I was 100% surprised by that but I;ll roll with it. “Hey, let me practice taking off your bra again?” “Oh, didnt you notice? Im not wearing a bra right now” And she lifts up her shirt and I can vaguely see her nice round breasts in the candlelight. “Thought you didnt want to show me your piercings” i tease. “Yeah well…” She says in an embarrassed tone. (I was sorta on the rebound right now after a mess with this one girl, so I let go of some of my boundaries from the last time). I go straight to sucking on her nipples, something I didnt do last time. Her piercings definitely made it tough to tease them in any way, I couldnt really bit on them, so I just kept swirling my tongue on it. She said that if she were to take them off they might bleed so, a guys just gotta stick with it. She slides off her shorts and panties. I noticed she starting trimming her pubic hair to be neater. Using what I learned, I went in for the clit, slowly teasing it as she starts breathing heavier and heavier. Since we were in her apartment, there was more leeway with how much noise she could emote. I take off my belt since its making her uncomfortable, unbutton my shorts to free my boner, and say fuck it and just take off all my clothes too. This is the first time Ive ever been naked in front of someone, so I was feeling really embarrassed. (Im 5’5ish at the time with some mass from the gym with a slight gut from not committing to a lean diet). My dick was out and pointing directly at her. I pull the foreskin back and lie in embrace on top of her warm welcoming body. We kiss a little bit more as I continue to feel her up and grind on her. By this time we had hit snooze on the alarm once or twice, till i got up and just turned it off. It didnt matter how long this took anymore. I wanted her. I could feel her frustration so I wanted to try nonpenetrative sex. I took the tip of my dick and searched for the entrance of her pussy to rub it against.
“What are you doing?” She asks
“Actually.. maybe its not such a good idea.” I backed out because I didnt want to do anything stupid. That’s when it hit me. Ive not touched her ass yet. I spoon her from behind and grab a bit of that fine ass of hers. Oh man latinas are blessed. I take my fingers covered in her juices and put it near her mouth. She wildly puts my fingers deep into her mouth and I lose it, I kiss her and taste some leftovers of that delicious salty juice. I finger her from behind and keep teasing her, and I take her hand and place it on my firm dick. She grasps the shaft and starts stroking.
“What happens if I keep going?” She teases me.
“Oh there;ll be a climax of course. But maybe you could help me out this time?”
“Welllll if i did that in this position, itd all be on you.” Wow I was surprised she was down to finish me off with the ground rules set.
“So I can cum on you then?”
“Yeah, but I’d prefer if it were in my mouth.” Wait. What. Oh fuck. What. Wait. What. My brain fried. Was this forreal?
“Okay.” I said as I sat up on my knees.
“Are you sure? It wont be going too far?”
“Well, for me sex is either vagina or anal so, I think a blowjob is okay” (Err this is debatable. Majority of people Ive talked to say a blowjob isnt sex but one or two have, leave me alone.)
As she lies down on her back, I straddle her torso and place my dick in her mouth as I mount the headboard of her bed. In goes the tip and in goes a warm wet sensation. Ohhhh godddddd. We tried this position for a few seconds but I could tell she was struggling so we swapped positons.
Now I am prone on my back as she is on her knees with her pussy hovering over my right leg. She slowly makes her way down to my hard dick (Usually Im like 5 and a half inches but I was so hard I swear I was at 6 tonight.) She slides her tongue up and down the shaft and tells me she’s not exactly a pro at blowjobs but she;ll try her best. From there I can see shes enjoying herself, appreciating the shape and getting intimate with my member. “Hey so, do you think you can go a little faster?” She gets a little embarrassed, gives me a cute face, and starts jerking off my dick with her hand. “Okay okay okay take your time!” I did not want to waste this opportunity with a simple handjob. I was promised mouth. I want mouth. She goes back to what shes doing, taking in my suggestion and going at a faster pace. I grab her hair with my hands and she takes my dick a little deeper in her mouth while making the sexiest eye contact ive ever recieved. I think she mightve gagged because I did hear a faint noise and a larger amount of saliva. I start moaning out of pleasure and to encourage her. She starts picking up momentum and starts swirling her tongue over the tip. OH MY FUCKING GOD. This puts me over the edge. “Ohhh my goddddd. Raven.. Im about to-” And there it goes. A fuckton of cum starts erupting out of my penis and i am blessed with the most intense, the most memorable orgasm of my life. She takes this like a champ and just collects it all in her mouth and swallows it whole. “Oh. Fuck.” Im left breathless as she is starts to situp. “Wow, that was a lot of cum.” “Yeah.. whats crazy is I jacked off today too haha” Then I feel a cold drop of liquid grace my leg. From there I see a string of grool stretch from the entrance of her pussy all the way to my leg. Oh my god. Raven was so wet and I have surely sinned for not giving her a good fuck. She sees me see this and she gets immediately embarrassed. “Im so embarrassed oh god” I laugh and say its hot as fuck. We calm down, cuddle for a bit, and she asks if I want to stay the night. “Im really sorry Raven, But I really like my bed. But I owe you. This was THE best orgasm of my life.” “Welllll, you’re welcome” and with that I get dressed, give her a wink, and take the late bus home, still shocked that my dick is still covered in her saliva and that she took in all my cum.
I message her later with a bunch of virgin questions. How did it taste. How did my dick size compare to others. etc etc (she said my cum tasted like nothing, I was a good size, some guys shes been with have been so big it hurts, but the guy shes currently fucking is a bit bigger :( ). We agreed this was a one time thing because.. It wasnt fair that she wasnt getting fucked. And I agreed. I craved her blowjobs and i masturbated to this event so many times, even to this day, but I didnt want to use her as a freebee for head. Her last bf only wanted oral from her and she , so i didnt want to be like that. We’re still good friends and I dont regret not fucking her.
Source: reddit.com/r/gonewildstories/comments/99mlqp/my_virgin_experience_fingering_a_close_friend_and
1 ‘st class post.
Nice to see a post where the guy mentions his normal size dong and not embellish it.