How I [F] took my [M] friends virginity

Disclaimer:- As always with my stories, this is long. It is about how I took my friends (soon afterwards – boyfriends) virginity and has a warts and all approach. If you want idealistic fantasy of a virgin guy making a girl orgasm repeatedly, this isn’t for you; but if you want something real, please read on. I hope you enjoy it.

My friends all think of me as a reserved, shy girl. Which on the surface is true. I don’t like being the center of attention and I am not especially extroverted. I had a couple of boyfriends over the years but nothing stuck. What they didn’t know was that the whole time I had been having fun with older men whenever I could get away with it. Having this secret double life excited me. For people to look at a boring; average looking size 10 5’4” girl, with shoulder length chestnut hair, brown eyes, round face and a button nose and have no idea the slut that live within – this seemed like the fun kind of secret. My friends were continually trying to set me up on dates, which usually ended the same way – they went home alone and so did I. I often had the comment from the girls that I must be ‘gaggin’ for it’ and similar things. I wasn’t – I made sure I got my fix.

My childhood friend Sam was a year older than me; we were hanging out on the eve of his 21st birthday. It was well known within the group that he had about as much charm with women as broccoli does with a five year old. He always tried to laugh it off but I knew their little jabs hurt him, so I always tried to change the subject. We were always close but totally platonic. Close enough in fact that he confided that he was still a virgin, and that he was conscious of it. I found this strange, he wasn’t bad looking at all. He was only around 5’10”/5’11” but he was well built. Looking back his problem was that he was too cute; he seemed to fall into the ‘Aww so cute!’ rather than the ‘Wow, he’s cute!’ category. Even to me. I couldn’t help but feel his problem was always one of confidence; he never had any experience so he wasn’t comfortable enough to try it on, so he didn’t get any experience and the cycle continued.

On the day before his birthday we went out together, the rest of the group were busy so it ended up being just us, first for dinner, then a movie and then back to his for a quiet couple of drinks. When we got back to his I made a joke about how I’d taken him out on a date (I paid since it was his birthday).

“I hope you aren’t expecting me to put out!” he jokingly responded. His expression turning more serious, “Is this how a date goes?” he paused a moment, “I wouldn’t know.” He smiled again, appearing to perk back up.

“No, I don’t put out on the first date; neither should you!”

“You put out on dates? News to me!” he opened a bottle of vodka and handed it to me. I poured some into the coke I had already in the glass. “You know you should put the vodka in first right?”

“I don’t have many second dates.” I swirled the alcoholic mixture together. “It’s still alcoholic.” I winked at him.

“I don’t get any dates. Can you believe I’m going to turn 21 and still be a virgin?” he took a long sip of his own drink. “How sad is that?”

“I don’t think it’s sad. Do you want some advice from me?” I waited for him to nod before continuing. “Today you were completely relaxed, you were yourself, and we had a wonderful day together. If you took a girl out like this on your first date you would have your pick.” He contemplated for a moment.

“The problem is that I’m too nervous.”

“I’ve seen you with girls, even some really pretty girls, and you don’t look nervous?”

“That’s different, there’s no expectation with them. There is nothing saying anything has to happen. I’m comfortable with that. It’s just with a date…” I stayed silent, hoping he was going to elaborate. “It’s just… It’s the sex thing.” He pretty much downed the rest of his drink.

“The sex thing? That’s what you’re worried about?” I tried not to appear as if I was mocking him.

“It’s just… by now people are expected to be good… and I haven’t ever done it…”

“Ha.” I laughed a little, “Sex is no big deal. Trust me, anyone who brags about how good they are is masking for something. Do you think you would feel more confident if you just had it and found out what all the fuss was about?”

“I don’t know… probably… like I feel it’s a massive social weight on me. The lads who know I’m a, well you know, make fun of it and when girls find out they are put off. It feels like a barrier.”

“What if you made it not a barrier?” he looked at me, clearly interested in what I was saying.

“How?” he chuckled to himself, “You gonna hire me a prostitute?”

“Oh no… you can do better than that.” I shifted my weight to lean forward on the sofa. I didn’t normally feel nervous; I suddenly did. I don’t know whether it was because I didn’t know how it would be received, how close it was to my usual social circle or whether I might actually like this guy. Whatever the reason I felt my mouth go a little dry. “How would you feel about not turning 21 a virgin?” he looked a little shocked as he tried to work out what I was saying.

“What do you mean?”

“Look, we’re both adults. Sex is no big deal. Why don’t I help you out? It doesn’t have to mean anything, it’s just doing it so you realise it’s no big deal.” I suddenly felt really silly and a little unsure of what I was doing. He stayed silent a little too long for me to be comfortable. I stood up, “I’m sorry, I should… er…” I tried to think of something to break the awkwardness.

“Are you serious?” he suddenly came out of his thought. “I mean, is that a real offer?” avoiding eye contact as he spoke.

“I think so. If you want?” My nerves beginning to calm down now. “I’m sorry if it’s made it awkward suddenly.” I sat back down, unsure of why I really stood up in the first place.

“I’d love to!” his excitement at the prospect bubbling up. “Are you sure you want to?”

“I guess today was like a date; I guess we can just think of it like we pulled. A practice run for next time you take a girl out?” he looked brimming with nervous excitement.

“How does it work?” he asked.

“You put the penis into the vagina, pull it out a bit and repeat until satisfied.”

“Haha no; I mean, how do you go from casual chatting to sexy time?” I guess it’s a genuine question, and one I couldn’t think of an easy answer.

“That depends, every situation is different.” I moved to the seat next to him. “Try to start getting close to them, take tonight for example, you could have sat next to me to have the drinks and suggested something on tv to watch. Try to get the mood more intimate.” I stood up, taking him by the hand. “Tonight though, we’ll get down to business. Come upstairs with me.” I was hoping he would make some pun about how he’ll cum with me, but he didn’t. I didn’t have high expectations for his performance, but I really wanted to have sex with him. I realised at this moment this probably wasn’t just a pity fuck. He followed me up the stairs, I could feel his excited energy starting to overrule his nervousness. He followed me up eagerly.

We entered his room and I sat down in the middle of his bed; he followed suit. “You should kiss me now.” I said bluntly. Hesitation for just a moment; he moved his body to line up with mine. I had enough of waiting so I leaned in, gave him a peck on the lips, then pressed harder with slightly parted lips – encouraging him to kiss back. He was enthusiastic and passionate; too much tongue but I didn’t mind. I could feel myself getting a little turned on as he swam around my mouth. I pulled away to catch my breath, he waited only a moment and leaned back in. We kissed until he was comfortable, he had relaxed finally, and I assume he was as ready as I was to move on. While we made out I felt his crotch. His hard cock barely held by his shorts. “What do you say we get these off?” Before I finished my sentence he was pulling them off. “Woah, slow down!” I joked.

“Sorry! Getting excited.” He yanked his top off, only a bit slower, and lay totally naked on the bed in front of me. He looked nice, and had a nice looking cock at about 6” but not so thick. Stroking it with my hand I could feel his heat, the way my fingers pushed a drop of precum out of his tip sent a quiver down my body.

“Have you ever seen a girl naked in real life?” I asked him.

“Err…” I started pulling my clothes off as he tried to think of an acceptable reply. As if I didn’t know. By the time he spoke I was finished and kneeled by his side. “You have nice tits… and…” he didn’t finish whatever he was saying. I moved his hand down to my pussy, encouraging him to have a feel. His probing fingers felt amazing, “So warm and wet…” sounding almost bemused.

“Yep, that’s pussy for you.” I leaned my head down over his stomach, “Want me to suck your cock?”

“Be my guest.” Came his borderline cocky reply. Wasting no time I kissed his throbbing cock, sucking the shining precum off the tip. Opening my mouth I slid my tongue down his length, closing my lips around as I sucked him hard. Up and down, I didn’t want to use hands, I wanted his first to be as good as I could do. He was silent, breathing heavily as I worked him. For a minute or so he relaxed as he oozed his salty liquid slowly into my mouth. At one moment he started rocking his hips into me, so hard I gagged and had to come away.

“Don’t do that!” I scolded him. Taking a second to regain composure, I could see he knew he’d got carried away. “You have to be gentle; gagging can really ruin both of our days. You don’t want teeth marks in your dick and I don’t want to throw up.”

“Shit I’m so sorry! I just…” I was already back to sucking and didn’t hear what he said after that. I worked him hard for a minute before I felt his first shot hit my throat. Instantly I moved up, just keeping his head in my mouth, using my hand to milk him as he filled it with cum. After five or six heavy bursts he leaked out a little more before it was clear he was done. His cum tasted great, he clearly drank a lot of water and ate a lot of fruit. Keeping his hot load in my mouth I sat up, making a point to show him that I was swallowing it.

“Tip for the future – give some warning. No girls like to be surprised.” Using my hand I wiped away the saliva around my lips.

“That was amazing.” He smiled radiantly. “And you swallowed? I thought girls hated that.”

“Some, it depends on mood for me. You tasted good so it was easy. Some of that shit is like battery acid.”

“How many times have you done that?” he inquired.

“Enough to know. Now…” I ran another finger over his cock, “You’re still technically a virgin and there are a couple of hours until you turn 21.”

“Can I lick you?” he blurted out, interrupting me. “Like on the… you know…” Laying next to him I lifted up my legs, I thought it would be more traumatic if his first experience was me sitting on his face.

“Just call it a pussy, or fanny, or cunt, or whatever. If you’re about to put your cock in it you should be comfortable will saying it out loud.” I laughed as I finished speaking. “Now are you getting your head between these legs?” he moved fast, not pausing for more than a moment. He lashed his tongue out, licking up and down the entirety of my lips, making an attempt to focus on my hood. His soft lips felt surprisingly good as his tongue probed it’s way around. Using my fingers I pulled my hood back slightly, exposing it more for him to concentrate on – he got the hint to take over.

Soon enough he was doing a good enough job I lost track of time, on the way to an orgasm but not quite enough. Still, I made sure to make a little noise to encourage him. He lifted his head up after a while, “My face aches.” He smiled, face glistening with my juices.

“Oral is hard, why do you think they call it a blow job?” we had a chuckle for a moment. He was now completely at ease. He was ready. “Are you ready to fuck me?” I asked seductively.

“Hell yeah!” He sat up, ready to position himself in front of me.

“What position have you always wanted to try?” I asked.

“Err… doggy? Maybe girl on top?” he seemed unsure.

“Doggy is a bit impersonal, on top would be better. Lay down again.” I gestured after sitting up. “This way you can play with boobs.” Sealing it with an awkward wink.

“Can I play with your tits?” I straddled him, balancing myself before grabbing his hand and pulling it onto my boob.

“If a girl is straddling you naked, you probably don’t have to ask to touch her boob.” I smiled, using my other hand to guide his cock into me. Sliding down his rod I saw him mouth ‘fuck’ and breath heavily. He felt great sliding into me, I was dripping wet and ready for him. His hand momentarily lost interest in playing with my boob before he remembered what he was doing. I slowly gyrated myself on him, “How does that feel?”

“Unbelievable! Uh…”

“Try to match my rhythm.” He made an effort but couldn’t quite get the timing right so I stopped moving, allowing him to work himself inside of me. His thrusts began to press themselves into the right places. So far, a half-decent job. I started to move in time with him, squeezing myself over his cock. Proving too much he tried to pull out but because I was on top he couldn’t, so instead I sat down and milked him. Using all I knew to milk him as he came hard in me. Once he was done I rolled off and waited for him to talk.

“Is it always that good?” he finally asked.

“Oh yeah; and the first time isn’t even the best.” Considering it was his first time I enjoyed it more than I thought.

“Best. Birthday. Ever.” He smiled, “Thank you so much.” I felt awkward that he thanked me.

“Don’t thank me, I had fun too.” I was still turned on and could feel the wetness of my juices and his cum leaking out between my legs. “It isn’t your birthday yet anyway. Tomorrow you can use your new found skill to screw a whole bunch of women.”

“What about if we practised a few more times?” he rolled on his side to face me.

“I think it’s too late to walk home by myself now…” he shot a real shit-eating grin as I spoke – his birthday was only just getting started.

Source: reddit.com/r/gonewildstories/comments/esh8cg/how_i_f_took_my_m_friends_virginity