An Unexpected Encounter

Story Info
That time I unexpectedly hooked up with a close friend.
3.2k words
4.72
38.4k
35
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

NOTE: I've changed the names in this story out of privacy concerns.

I have a great circle of friends. First, there's my roommate Kelly who I've been best friends with since high school, and who went to the same college as me. She has a boyfriend, John, who is funnier than a person has a right to be.

There's Sarah, who became friends with Kelly first and then became part of our group. She is one of the smartest and kindest people I've ever met.

There's Dennis, my "friend with benefits", who even though we tend to go through periods of fighting, is still one of the better people I've met.

And finally, there's Heather. I've known Heather since our freshman year of college, when we were both in the same English 101 class. It didn't take long for us to hit it off and for her to become close friends, with me and everyone else in our group.

Over a year ago, Heather began to date a guy named Rob, and the two of them became a very serious item. I wouldn't be surprised if there was an engagement taking place in the near future. They are an adorable couple, and Rob has fit into our little group seamlessly. But Rob's job takes him out of town on occasion, which was the case on this one weekend a few months ago.

I was invited to a party by some other friends who we all know, but who were not part of "The Circle". Kelly and John had decided they were not going to go and instead were having "date night" at John's place. Dennis and I were fighting at the time, so Heather and I went together, and we met Sarah there as well.

The party was fun, and Heather and I both had more than our share to drink. Heather had driven over to the townhouse that Kelly and I share, and we had taken an Uber from there to the party. Sarah had also taken an Uber from her place, and she left a little before us to take one back. At about 1:00 am, Heather and I took another one back to my place.

We were both still buzzed when we got back to my place. I told Heather that under no circumstances was I going to let her try to drive home tonight, and she agreed. I told her that she could have my bed, and I would sleep on the couch. Heather flatly refused. She said she would never kick me out of my own bed just because, as she put it, "my drunk ass can't drive". Heather of course had not brought anything to sleep in, so I tried to find her something to wear, but that was an issue.

Heather is not my size, and actually, except for both of us having blue eyes, we don't look like each other at all. I have long blonde hair; Heather has wavy reddish-brown hair that comes just past her shoulders. Heather is 5 foot 7, compared to my 5 foot 4. I will say that we're both in fantastic physical shape. Heather, Kelly, Sarah and I spend a lot of time at the gym, and all we push each other, which helps us all stay in great shape.

But then there is the coup-de-grace for Heather. I am lucky enough to have C-cup breasts. When I want them to, they can bring upon me the attraction of whoever I want to attract. But Heather has a set of the most perfectly shaped, round, 100% natural D-cup breasts that I think are allowed by law. It's like thinking "I sure am proud of that painting I did in art class", only to have Van Gogh himself show up at your door. If Heather wasn't one of my favorite people on the planet, I'd probably hate her for them.

All this is to say I probably didn't have anything that was going to fit her. I spent a few minutes going through my clothes and trying to figure out what to do, but Heather decided for us both, and took off her shirt, skirt, and bra. She got into bed wearing only her panties.

I was a little surprised by this. And, to be honest, I was starting to feel that familiar feeling between my legs at the sight of her almost naked body. I have fully embraced that I'm bisexual since I was 16, and I've been lucky enough to be with my share of women. So, this wasn't the first time I had had a naked female in my bed. But it had never been one of my closest friends.

All my female friends know I'm bisexual. They are all very supportive of me, but I've always made it a point to never look at any of them sexually. We were friends, they're not my reserve of possible sex toys for when I felt the need. But seeing Heather laying there, looking as beautiful as ever, with her entire body on display...my mind was racing. I quickly changed out of my party clothes, put on a comfortable pair of cotton panties and a t-shirt, and got into bed next to Heather.

My bed is not a big bed. It's a full, one size up from a twin, but it's big enough for me for now. I can comfortably sleep in it. However, it's not possible for two people to sleep in my bed without touching the other person. A lot. Every time I've tried to fall asleep with someone else in the bed with me, we touch. But, all those times, the two of us had just made love. In that situation, you don't mind the closeness and the constant touching. That was not the case this night.

I turned out the light, but then switched on the lamp I have on my bedside table so I could see as I got into bed. Heather was laying on her side, her back to me. No matter what I did, I ended up touching her. My leg would brush against her leg, or my hand would rub against her back. All this was causing the wetness between my legs to increase. She was turning me on, simply by lying next to me. I was thinking about making a trip into the bathroom to "relieve some pressure" when Heather turned over to face me.

She had only pulled the blanket up to cover her legs, so not only was I now staring at her beautiful face, I was also getting an eyeful of those stunning, perfect breasts of hers. I stared at them. I couldn't help it. Then, I realized what I was doing, and that Heather was wide awake, and looking right at me. Our eyes locked, and for what seemed like ages, we stared deeply into each other's eyes. Then Heather broke the silence, and said "you are so beautiful Jess".

I couldn't hold myself back any longer. I leaned in and kissed her, and she kissed me back. The tiny amount of clothing we both had on came off very quickly. I could tell Heather was nervous at first, but also very aroused. When I slid her panties off, she was already so wet I could smell her. And she smelled wonderful, so turned on and ready for anything. There was still a part of me saying "this is a mistake! This is Heather! This is a bad idea!". But I was so turned on I didn't care by that point, in big part because it WAS Heather. I couldn't believe that this was happening, but I was so excited that it was.

I would've sworn before that night that Heather was 100% straight, no interest in girls at all. I know that she had never kissed a woman romantically before, and certainly had never made love with another woman. But, the things she did to me that night, and how well she did them...it was unbelievable.

We were now both naked. I climbed on top of her, grabbed her arms, and pinned them over her head. I started deep kissing her and grinding against her with my body. She is such a good kisser too. I'm kissing her and grinding on her, and she wraps her legs around my waist and pulls me tight against her. That was one of the sexiest things I've ever had done to me in bed, and she hadn't even really touched me yet. I swear, I almost orgasmed from her doing that alone.

We spent a long time kissing and grinding on each other. Eventually, I let go of her arms, and she started running her hands all over my body. Through my hair, down my back, and I was doing the same to her. Her skin felt so incredible, so soft and silky. She still had her legs wrapped around me, and she was using them to rub my lower back and butt. I began to slide out from them and down her body, kissing her neck and collar bones, and then her upper chest.

I got to her breasts, and her nipples were like steel they were so hard at this point. I started sucking on them and then lightly biting them. By this point Heather was moaning and panting, and arching her back when I bit her nips. After playing with her breasts for a while, I started sliding lower, down to her abdomen. She parted her legs wide at this point, and I started doing something that I do best, and which more men need to do during oral sex...teasing.

I started by kissing her inner thighs, her inner knees, and the space between her pussy and asshole. I moved my mouth all above and around there, making sure she could feel my breath on her pussy...but never touching it. And of course, this was driving her nuts, which was the plan. She was moaning and gasping and writhing on the bed, and grabbing at the sheets. Her skin was so warm it felt like it was on fire, and finally she started actually begging me to lick her.

After a few more moments of letting her squirm, I finally licked her, with the tip of my tongue, the whole length of her pussy. The moment my tongue touched her pussy, Heather arched her back hard up off the bed and grabbed her breasts. She started shouting out to me and to the heavens and to whoever else could hear her, and pleading for me not to stop. I could tell that she was not going to last long, no matter how I tried to prolong it. Instead, I decided to go for it and see how big I could make her orgasm.

I slid two fingers into her, and she gasped when I did. I curled them up and begin to rub her from the inside, and at the same time I planted my mouth firmly over her clit. I began to suck it with my lips and tease it with my tongue. That instantly drove her over the edge. I felt her pussy start contracting around my fingers, and she started cumming. It's one of the most beautiful orgasms I've ever seen a woman have. Long and loud, her head thrust back and her mouth wide open. Not shouting anything in particular, just shouting because she has to let it out. Her whole body was tensing and shaking as it went on and on. It was magical to see.

When she finally came back down from her orgasm, she said she wanted to do me, but I decided that we were going to do a 69. I swung my legs up over her head and got above her, and we start eating and fingering each other.

Now, like I said, Heather had done nothing with another woman before, not even a kiss or anything. But her tongue and fingers while we were 69ing felt like a gift from above. She was so good, I was having a hard time remembering that "oh yeah, we're doing a 69, I need to eat her out too". And even though she had just cum really hard when I had gone down on her, she started cumming again.

As she did, she grabbed my hips with her hands, and pulled me tight to her. She latched her mouth onto my pussy, and I could feel her lips humming. I had been fighting hard to maintain some composure during this. That had already been an impossible task, but when she did this, I completely lost control. My hands gripped hard onto her thighs. I started screaming her name and yelling at her to please not stop because nothing could ever feel this good and I didn't want it to ever end. It was one of the most explosive orgasms I've ever had.

We both lay there for a bit, catching our breath. I'm sure I was in shock at this point. I couldn't believe that, of all people, Heather had just given me one of the best orgasms of my life. Gradually, our hands started moving again over each other's bodies, and we started making out again. She really was an incredible kisser. We were kissing and getting more and more turned on again by the second, and I decided I wanted to trib with her.

I could see she was kinda skeptical at first, which I understood. You see tribbing so much in porn, and so often they don't do a good job showing it. You think "well, that must be fake, not a real thing". But I climbed on top of Heather, and we scissored our legs together. I started grinding our pussies together, and she started moving her hips and body in rhythm to me. I had her left leg lifted up high and was holding it against my chest. We both locked eyes and were staring deeply at each other, and she was not quiet, not in the least.

When I'm doing another girl, I love it when she's loud, and every time I thrust my pussy back and forth over Heather's, she made like this wonderful half grunt, half whimper noise that sounded incredibly sexy. She was also arching her back again. Heather was a back archer. And that is so sexy too, especially when you know the reason she's arching her back is because you're fucking her. I started increasing my rhythm and pace. At that moment the only thing I wanted in the world was to make her cum again. I wanted to see her cum. I was above her, looking right into her eyes, and all I wanted to see was the reaction on her perfect face while I made her cum.

I moved faster, rolling my hips deeper into her, and I was still staring her right in the face. She was matching my pace, and I could tell that she was desperately trying to maintain control and not cum yet, but that she was about to lose that fight. Her head was up near the headboard, which was pushed up against the wall. I leaned forward so my head was above hers, and steadied myself with my left hand against the wall. This pushed her leg back towards her body as well, which really opened her up between her legs.

That was enough to make her start to cum again, and it was the single sexiest thing I'd ever seen. Her back arched again, like so hard I almost thought she was going to hurt herself. Her eyes were shut tight, and she was grabbing and pulling at the bed sheets. Her mouth was open, and she was screaming my name over and over. Seeing that was more than enough to push me over the edge again too.

I was grinding against her as hard as I could, gripping her raised left leg tightly to my chest. I had what still was the biggest orgasm I'd ever had. Have you ever had one of those orgasms where you can feel it start deep in your pussy, and then it spreads all over you? It tingles up your spine to your head, radiating out everywhere? This was one of those, the most intense feeling I could imagine. It's a good thing Kelly wasn't home that night. I was yelling so loud that I'm sure the people next door and across the street heard me.

We were both exhausted after that, so we pulled up the covers and turned out the light and fell asleep. When we woke up around noon, my first thought was to remember what we had done the night before, and to think that I hoped this wasn't about to turn awkward. I got up, and I tried to act normal. I said that we should get breakfast, but that first I was going to take a shower. Heather got in the shower with me, and we fingered each other, making each other cum again. I figured this meant she was fine with the night before. Ha!

The next four weeks were kind of a blur. Heather and I got together and had sex as much as we could, but for obvious reasons we had to keep it a secret. Every time my roommate was going to be spending the night at her boyfriend's place, I would text Heather to let her know. We'd both make up an excuse why we were going to be hanging out, just the two of us. Then Heather would then come over and we'd spend the night making love.

And it was always some of the best sex I've ever had -- every single time, without fail. Even though she had never done anything with another woman before that night, deep down I'm sure Heather had these feelings hidden. That night everything aligned right and she let them out. But you know there's that saying about all good things coming to an end.

After about four weeks of sneaking around, we decided to stop. Dennis and I were still in a fight and not talking much, but Heather and Rob were as strong as ever. Both of us had become increasingly worried that he was going to find out. Of course, it was possible that he would have thought it was great what Heather and I had been doing. What guy isn't going to get turned on by the thought of his girlfriend sleeping with another girl? But it was equally possible that he would be mad because she and I had been doing this behind his back.

Heather and I remain the closest of friends. The friendship among our circle of friends is still very tight. She and I never talk about it, and we've both decided to leave that part of our relationship in the past. Somehow, we managed to keep it a secret -- no one ever found what we had been doing with each other for that month. But every now and then, she'll look at me with this sly little knowing glance. I'll know that she's remembering, like I always do.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
ChumulyaChumulya3 months ago

A quite enjoyable read.

wc2728wc2728about 1 year ago

Outstanding!! Great story in all aspects, but especially in terms of being hot and sexy. Thank you very much! I'm anxious for more!

christa_pchrista_pover 1 year ago

I really enjoyed this, hope you write more!

hot_jessicahot_jessicaover 1 year ago

I appreciate this story x

JachmastJachmastover 1 year ago

I have just read your story about an unexpected encounter and it is one of the best I have seen. Your writing style is easy and it takes the reader the story that makes you feel that you are there.the tale is highly erotic and leaves you fulfilled yet wanting more. I hope you will continue writing such stories in the future

Show More
Share this Story

Similar Stories

More Than Okay Eve accidentally inspires her roommate in lockdown.in Lesbian Sex
Turning Straight Straight girl unexpectedly gets drawn into an encounter.in Lesbian Sex
Bedding the Trophy Wife Lesbian seduces the straight wife of a homophobic coworker.in Lesbian Sex
Nanny Sarah Hiring a nanny will change Connie's life forever.in Lesbian Sex
Straight Girl Problems Her BFFs are straight. There's a first time for everything.in Lesbian Sex
More Stories