My lesbian friend and I crossed the barrier [MF]

Back when I (M24ish) was still a server, I had a friend at my job named Holly (F22ish). I loved Holly, she was super sweet, super funny, was a stoner like me. She was a little taller, maybe 5’7 or so, real slim, small breasts and not too curvy (or so I thought), she had strikingly beautiful eyes and such a sweet smile. She was more of the tomboyish lesbian. She had a typical male looking wardrobe, kept her hair cut short kinda pixie style, and I don’t think I’ve ever seen her wear makeup. She was very clearly and obviously a girl, nobody would ever think she wasn’t she had such a natural beauty to her, but if you saw her walking from a distance without clearly seeing her face, you might have thought she was a guy. She had a habit of getting into stupid situations and shenanigans, and I was constantly giving her advice or listening to her vent about her current ridiculous circumstances, but she was awesome.

Holly and I never really flirted persay.. I knew she was 100% into girls and I never hit on her, we just had a close friendship. At some point, don’t remember how it started, maybe we were all drunk at the bar or something, but I knew Holly thought I was very handsome and the phrase “if I was into dudes…” was used by her in relation to me. Again, awesome, but nothing came of it.

One day, I don’t remember what had changed or how, but Holly and I seemed different. Hugs were a lil longer and felt more intimate, I was actually LOOKING at her, conversations seemed a bit flirty.. idk, it was just different. Can’t remember the events that led up to me doing this, but one day she was venting to me about something or other at work, and when she was leaving for the day I walked out after her and just walked up and kissed her, full on. Don’t know why, but I just did. And to my surprise she reciprocated. We stood by her car kissing for a good ten seconds before breaking. Her face was red, we both kind of laughed, I apologized and she said it was okay, and that was that.

After that Holly and and I went back to normal but things were different, you could just feel it. We sat next to each other much more often, way more hugs than usual, she would be right next to me more often than not if we were hanging with other work friends, she came over to chill more often, etc, but nothing overt that anyone could tell. One night, she’s texting me about some issues she’s having and I told her to just come by and smoke, we’ll watch a movie or go to the bar, whatever. She tells me, and I remember exactly what she said, “I definitely want to come through, I’m just kind of nervous of what might happen..”. I knew what she meant of course but Holly was one of the few I wasn’t actively trying to fuck.

For one thing she was my good friend, and another I knew she loooooved pussy, so it’s not like I honestly had a chance. So I feign ignorance asking what she means, and she goes on about how she’s never been with guy, she knows I’m big (I definitely was a ho during this stage of my life and I had worked at the restaurant for a couple years at this point, I had been with my fair share of girls at my restaurant). I told her straight up, I’m her friend she’s mine and that’s whats important, and I’m not expecting shit from her. And I 100% meant it. So she comes through.

When she gets to my place sometime later, she had a bag with her, and when I opened the door she asked if she could crash at my place because of whatever was going on with her roommates. Of course I obliged. We went into my room and spent the night smoking and talking and watching random shit on tv. At some point she was lying on her stomach on my giant ass bed, and asked me if I could get this knot out of her back. I’ve always loved giving massages and I think they’re one of the sexiest things people can do to each other, so absolutely. I rubbed her neck for a bit, she was into it, so I asked if she would want a full on back rub and she says yes.

I straddle her and start rubbing her back and I lift her shirt a bit so I can get to the skin. Of course I enjoyed touching Holly’s bare skin like this, but I kept that to myself and just wanted her feeling comfortable. Once I started making my way a little bit more up Holly raises up for a second and just lifts her shirt off. She was wearing this strange elastic strap thing. It wasn’t a bra, it was just an elastic band that wrapped around her breast I guess, I asked her about it and she straight up said she wears it so it’ll flatten her chest down some. Ah okay cool. Immediately it was getting in the way, so I just asked if she’d be all right if I unsnapped it and she said yeah so I did.

With the lotion I rubbed her whole back her arms her shoulders her neck while she just laid there enjoying every second. Eventually I started going down towards her hips and I asked her if she wanted me to rub her legs as well, and she said “hell yeah I’ll take a full body rub down”. I started at the bottom and started to work my way up her calves. She was wearing basketball shorts and I wasn’t about to push my luck so I just rubbed my hands up her thighs, but she tells me I can take those down if it’s easier. This was the moment I started getting nervous. I’m thinking holy shit, Holly is gonna be pretty much butt naked in my bed.

I played it like it was no big deal, and started to pull down her shorts as nonchalant as possible to see she’s wearing a thong, (which I didn’t expect, I figured she wore boxer briefs or at the very least those booty short things girls wear) and… Holy shit, Holly had a booty. Like a booty booty. Like a curvy plump booty. I was a bit perplexed, but it only took a second for it all to make sense.. Holly always wore baggy clothes, clothes designed mainly for males. Hell, she even wore a larger baggy male version of our server shirt, loose fitting slacks with the server apron on… Of course I had no idea what her body really looked like.

I couldn’t help but let my mind wander, and by this point I figured I knew what would end up happening but I wasn’t going to push anything. I lotioned up and went to work, rubbing and massaging her calves, thighs, glutes, then her ass.. I took my time rubbing each of her cheeks and squeezing them. She was sighing contentedly, letting out a soft pleasure moan every once in a while. I decided to risk it.. I started sliding my fingers closer to the private zones… Fingers in between her cheeks, sliding between her inner thighs, getting close to her pussy and ass. I heard her breath catch every once in a while and right there and then I decided to go for it.

I switched positions kneeled behind her and just went for it… I took her thong and started to slide them down slowly and… She didn’t say a word or make a sound. Instead she simply raised her hips a bit.. and I pulled them the rest of the way down. I started massaging her ass in earnest, spreading her cheeks, using my thumbs to grab the edges of her pussy and spread them so I could stare at it all. By this point Holly has been letting out soft moans constantly. So I really went for it.

I took Holly and turned her over to lay on her back, and surprise surprise, she had nice tits too. I always thought she was just flat.. idk shit about bra sizes but I’d guess they were a nice B size, a nice handful. I of course looked at them, but I just quickly leaned in to kiss her and she put her arms around me and kissed me back. We stayed there kissing each other passionately until I raised up.. as I’m taking off my shirt, Holly started undoing my pants… As the shirt came off I leaned forward to kiss her again. Her hands are fiddling with my button and zipper until I reach down to help, my lips still on hers. I finally get it and she starts to slide my pants down, and I just pull them straight off… Awkwardly, but I got it.

My cock was already understandably hard, but Holly just grabs it and I swear my cock throbbed even harder. Both naked now, I was surprised when Holly just immediately tried to put me inside of her… And it went NOWHERE. She was so tight it was unbelievable… Extra extra tight. But she was also soaking wet which was nice: I was actually turning her on she wasn’t just doing it to do it.

I reached down to try to tease myself inside her a bit, but it just wasn’t happening and I could tell it hurt her a bit. So I did the next best thing, and used my fingers. I started with one, and damn she was tiiiiight. But her moans… Her moans were everything. Well if we couldn’t fuck, I would just pleasure her… I want going to try to have her suck my dick or anything, we had already gone way further than I could have imagined. So I slid down and put my face in her pussy, which was apparently the right choice. She immediately grabbed my hair and started pulling my face harder into her. I was licking her everywhere I could and she seemed to be getting more and more turned on… Her back would arch, she would move her hips up and down, basically riding my face. I would spread and raise her legs a bit then slide my finger back in. I licked her asshole a bit and she would giggle a bit saying it tickled, but she liked it. I put another finger inside of her. Then after a bit I tried another finger.

I stopped and made my way back to her to kiss her some more, 3 fingers deep in her. She seemed in full go mode by this point, just grabbing my hair and biting my lips. I pulled my fingers out and went for it again.. this time, there was a bit of resistance, but my cock finally slid inside of her and she let out the sexiest gasp… I won’t lie, I thought I would cum right there. I slowed way down until the feeling went away, and I just made love to Holly. Sounds corny I know, but that’s the type of sex we had. We weren’t slamming each other’s bodies as hard and fast as we could, we weren’t screaming or slamming anything, just some relaxing smooth fucking.

She asked if she could get on top which of course I said yes. It was a little awkward at first, there were some chuckles had when she said she’s just gonna “do what I do with my dildo”. But she rode me just how I like… She squatted down and grabbed me and slid me inside of her, went in nice and easy at this point. We got more and more into it, our bodies and minds sliding deeper into pure lust and ecstasy. She and I were both moaning in earnest, kissing each other passionately. She had an orgasm riding me and started to shake a little.. But she resumed riding me. Unfortunately I was already about to cum… That’s the downside of foreplay for me, I get so turned on that it’s easy for me to cum.

In my head, I knew I didn’t want to cum in on or near her… This was already way past the line of anything I would have imagined with her, who knows how she would have reacted. So I told her I was about to bust, and she slid off of me and, surprisingly, just laid straight on top of me and kissed me madly, while my cock just throbbed and burst in between us, getting my cum all over both of our stomachs.

We kept kissing for what seemed like an eternity. It was bliss. When we started to calm down, she just stayed on top of me with her head nuzzled in my neck. I stayed rubbing her back and her ass just enjoying the moment. After a bit, we decided to take a shower. I turned the lights off and we soaped and washed each other down, laughing and hugging and kissing in the shower. When we got out, we laid in my bed with minimal clothing, watching tv, and just chatting. Holly said she was very much a lesbian and she doesn’t fuck with guys, she was just also strangely very attracted to me. We decided it best not to tell anyone for obvious reasons.

The next morning we woke up still cuddling. We chatted for a bit until we started kissing, morning breath and all, and she climbed right back on top of me and went at it again. This time was somehow even better, both of us sober and alert.. we had full on raging boners for each other. Holly and I continued hooking up regularly, pretty much 3 or 4 times a week, until we actually caught feelings. We talked and decided we wanted to be together, but it’s obviously wasn’t going to end in us getting married or anything, so we decided to have an open relationship.. she could date/go out/hook up with any girls she wanted and I could do the same, as long as we still had our time together. We took full advantage of it.. soon after I started hooking up with another girl at work, Abby, and funnily enough Holly hooked up with Abby some as well. It was admittedly a strange situation: Abby would talk to me about how she hooked up with Holly, but she had no clue that Holly and I were together, nobody did.

Holly and I stayed together until I got promoted and went into management. It was a mutual and amicable “break up”. We still hooked up some here and there, but with my busy schedule training, I just didn’t have the time to see her as much. We still keep in contact and are still just as great friends as we were before.

Source: reddit.com/r/gonewildstories/comments/tvejrf/my_lesbian_friend_and_i_crossed_the_barrier_mf