Amy, Sarah, Mary, Josie and I were all hanging out in Amy’s pool at her vacation house in Florida, having some drinks in the early afternoon.
I was pretty shocked at the story my gf Amy just told us about the summer after she graduated high school. But, I felt like a hypocrite considering she was allowing me to have sex with three other girls.
I said, “Well, Amy that was surprising but kind of a hot story.”
Amy said, “Does it bother you that I fucked all those guys that summer?”
Before I could say anything Josie said, “Who cares, you’re letting him fuck us right now. Why haven’t you wanted another dude in this group is a better question?”
Amy said, “I kind of did that already. I feel like I have experienced that and it was fun, but I don’t need that now. I am happy with you girls and Jack. I feel like another guy would mess things up.”
Mary said, “I’m kinda interested in a spitroast,” and she was blushing and looking down.
Sarah said, “Amy, you said you hooked up with those two lifeguards all summer, sometimes one on one and sometimes together. Did you get spitroasted multiple times?”
Amy looked at me embarrassed and said, “yes, that was something we did sometimes. I liked getting fucked missionary, with the other guy kneeling near my head with his dick in my mouth. Sorry Jack. Sarah haven’t you been with more than one guy at once?”
Sarah giggled and said, “I have sucked two dicks at the same time. I have not been spitroasted.”
Amy said, “Jack have you ever fucked a girl with a friend. You know two guys on one girl?”
I said, “No, I don’t think I would like that. I don’t really want to share a girl with some other dude at the same time. Um, I have shared a girl with friends, just not at the same time.”
Amy said, “What do you mean?”
I said, “This is going to sound bad. I’m not telling you who the girl was.”
Amy said, “We know her?”
I said, “Yes, she goes to school with us.”
Amy said, “Well I respect that you don’t want to hurt her reputation.”
I said, “Alright, a couple of years ago, we had that big blizzard, right after Christmas break.”
Mary said, “I remember that.”
Everyone else nodded.
I said. “We had a party the first night of the blizzard. Most people lived really close by and walked home. My friend, I will call her Tiffany, stayed the night with us guys. She was good friends with all of us. There were three of us who shared a house.”
Sarah said, “I’m 99% sure I know who you are talking about, but I won’t say anything.”
I said, “that first night, she hooked up with my housemate Rob. She slept in his bed. They had hooked up previously. In the morning, we all sat around the kitchen table having coffee. She was wearing one of his tshirts and some of his boxers because she only had the clothes she wore to the party. It was still snowing out.
We were excited because classes were cancelled. Drinking coffee turned into drinking beers, playing drinking games around the table. Rob went to take a nap in his room in the afternoon. He wanted Tiffany to come, but she did not feel like it. My other housemate Will, also went off to nap in his room. Tiffany and I were hanging out drinking, listening to music.
Tiffany said to me, ‘Do you wanna take a nap with me?’ I had never thought about Tiffany that way. She was not really my type, but she was hilarious and she was pretty cute.”
Amy said, “What’s your type?”
I said, “you can look at each other and tell what my type is.”
Mary said, “we don’t really look the same Jack.”
I said, “You are all pretty thin. Tight asses. Thin legs. Sarah is taller and Amy has slightly bigger boobs, but you are all pretty thin, tight bodies.”
They all seemed satisfied with that.
I said, “let me continue. Tiffany is attractive, slightly chubby, but not fat. I shouldn’t even say chubby, just not as thin as you guys. She has smallish tits and a bigger ass, but not a fat ass. I don’t know, it was not about looks really, she just was always more like a sister to me, never thought about hooking up with her.”
Sarah said, “I definitely know who this girl is. She is cool and I think she is pretty cute.”
I said, “I did not really think we were going to hook up. I thought we would get in my bed and snuggle and have some laughs. She and I had previously done that sort of thing. We were pretty close friends. We got in my bed and started snuggling. We were having some laughs. But, I noticed she started rubbing her feet on my feet. And squeezing my foot between her two feet like a hug.”
Amy laughed and said, “Playing footsie – that whore. But, seriously that is a good way to let a guy know you want some.”
I said, “I still didn’t get it.”
Amy said, “Holy shit Jack. Now I understand why I had to flirt with you for three years.”
Sarah said, “I had to invite Jack back to my place and have him unzip my dress. That was not obvious enough, so I had to tell him to come with me to bed.”
Josie said, “I had to fucking invite myself
to his room and take off my shirt.”
I said, “Josie, wait, you were flirting with me that night before we went to my room?”
Josie said, “Jack, you’re fucking clueless! I talked to you, and only you, at your party. I couldn’t have made more direct eye contact. I was sending you sexy looks.”
Mary said, “We all know Josie knows how to be sexy, you’re clueless Jack.”
I said, “Alright, fine, I’m clueless. Josie, I was fucking intimidated by you. You’re so fucking hot. And, Sarah, you’re so hot and taller than me. I didn’t think you would hook up with me. Mary, you and I never hooked up before this situation, but I would have been intimidated by you too. Amy, you know you’re hot and I crushed on you so hard since freshman year and we had so much fun in lab, I just couldn’t stand it if I made a move and you rejected me.”
They were all blushing a bit at that.
Amy smiled and said, “Well, I’m glad you eventually got with all of us, even if we had to hit you over the head.”
I said, “I’m embarrassed now, so back to the story…Tiffany was looking right at me and slowly ran her hand down my chest, down my abs, and into my boxers. She started slowly stroking it.”
Josie interjected, “So, once she touched your dick, did you realize she wanted to hookup?”
All the girls laughed at that.
I said, “Very funny Josie. I started feeling her body and I was thinking I’d like to see her naked. I said to Tiffany, ‘You hooked up with Rob last night. What did you guys do?’ Tiffany said, ‘We made out. I gave him a handjob and he fingered me a little. He came and then we both passed out. Why?’ I said, ‘Well, I’m kind of thinking of going down on you, if you want, but not if you fucked Rob last night.’ She giggled and said, “I haven’t fucked anyone in a long time and yes…you can do that.’ She kind of bit her lip looking at me nervously.”
Sarah said, “You really do love eating pussy.”
I said, “We started kissing and I was feeling her ass. She pulled off her tshirt and was not wearing a bra. She had nice smallish tits. I made my way down to the boxers she was wearing. She had a slight belly, but it was cute, not big. I pulled off the boxers. She had nice legs, a little thicker thighs, but they were nice. She had really light blonde hair and so she had some blonde bush, but neatly maintained. I went down and she spread her legs, with her knees up. She was sort of biting her finger looking down at me red faced and nervous. I started licking her and fingering her. She was breathing heavy, panting. There was lots of afternoon light in my room, that overcast sort of afternoon light reflecting off the snow, so I got a nice view of her pussy and naked body. I liked what I saw. I was pleasantly surprised. I licked her a long time and made her cum multiple times.
She laid there, her chest heaving up and down a minute after she came. She made her way down, pulled off my boxers and sucked my dick. She seemed kind of nervous doing it, but she was good at it. She gave an embarrassed laugh and looked up at me red faced. She said, ‘i can’t believe I am doing this. Don’t cum in my mouth. Tell me when you’re going to cum.’ She licked and sucked it. She kept going a long time. Then I said, ‘I’m going to cum.’ She pulled her mouth off and slowly jerked me off while looking up at me with her face near my dick. I came on my stomach. I grabbed an old tshirt and wiped it off.
We laid there naked, touching each other and sort of drifted off to sleep. We both woke up and she said, ‘I don’t usually do that on a hookup Jack.’ I said, ‘Do what?’ She said, ‘All of that. I have only done oral with a real boyfriend.’ I said, ‘Oh, what do you do on hookups?’ She said, ‘Really, I usually just give handjobs, maybe let them finger me or touch my boobs.’ I sad, ‘Why’d you do that with me?’ She said, ‘I don’t know, I was really nervous, but I was feeling…horny.’ She was embarrassed and avoiding eye contact.
Then she said, ‘Would you maybe, do that some more…’
I grinned and said, ‘Do what?’
She said, ‘Don’t make me say it.’
I laughed and said, ‘you have to tell me.’
She said, ‘Jack…come on….’ I just looked at her. She said, ‘lick me some more’ and she covered her face with a pillow in embarrassment.”
Amy said, “I know you and I know you went back down on that girl.”
I said, “Of course, she had a pretty pussy and she enjoyed oral. It was fun eating her out. She really got into it the second time. And so did I. I ate her out a long time. She was cute with her face flushed and she was whimpering. After she had a particularly intense orgasm, I moved up grinding my boner into her crotch. She said, ‘Jack, do you have a condom?’ I said, ‘Yes,’ and I put one on. I told her to get on all fours and I fucked her doggystyle. She had that nice ass sticking up at me. It was rounder than other girls I have been with but it was not flabby and it was nice fucking her like that.”
Amy said, “I’m dying to know who this girl is. I’m kind of thinking I want to check out this body myself.”
Sarah said, “If it is who I’m thinking it is, she’s fucking cute and yeah, I would.”
Amy laughed at that.
I continued, “We finished up and took a shower together. We went back upstairs to the kitchen and the other guys were back up drinking beers, playing a board game. It was snowing again. We all ended up getting pretty hammered. She passed out on our basement couch while we were watching movies. It was a pretty comfy couch. We put a blanket on her, left her a glass of water and we all went to bed.
I woke up in the morning when she came into my room, which was also in the basement. Tiffany climbed into bed with me and kissed me. I could tell she had brushed her teeth. I got up and peed and brushed my teeth and came back into bed with her. We joked around some, but ended up making out and I went down on her again. She sucked my dick again.
We went upstairs to get some coffee and hang out with everyone. I started getting a feeling like this was more than a hookup for her. I don’t know, I felt like she wanted more than that. I really liked her but I didn’t want to date her.”
Sarah said, “You said she was cool, hilarious, sounds like you thought she was attractive, why didn’t you want to date her?”
I sighed and said, “Because…I had a huge crush on someone else,” as I looked at Amy.
Amy said, “Jeez Jack, that was two years ago. Why didn’t you ever make a move on me until this year?”
I said, “I was worried it would mess up what we had if you didn’t want to date me.”
Amy said, “You’re so fucking adorable. But, seriously, have you ever asked a girl out instead of waiting for her to fall in your lap?”
I was embarrassed and said, “you did literally land in my lap Amy. I have made the first move at least once. But I have been lucky in that regard. I’ve been set up on dates with girls I liked and I’ve had a bunch of girls make the first move. I’ve made the first move for some hookups.”
Amy said, “So, you just hooked up with random chicks to satisfy your sexual needs without getting too attached while waiting for me? That is somehow oddly romantic. What happened with Tiffany?”
I said, “I pushed Tiffany away. Not literally, but yep I think she could tell I did not want to be more than friends. Will was into her.
I didn’t know that before I hooked up with her, but I could tell as we all spent 5 days trapped in our house in this blizzard.”
Sarah said, “This Tiffany girl was trapped with three boys alone during a blizzard. I mean that doesn’t sound that bad.”
I said, “Well, she ended up hooking up with Will one night. He came to me to see if I had a condom and I gave him one.”
Josie said, “So, she hooked up with all three of you.”
I said, “Yep. And she came to my room again one night for some more fucking. Against my judgement, I fucked her again and she slept in my bed. I didn’t go down on her, but I fucked her twice. Once at night and once in the morning. That morning Will seemed irritated.”
Amy said, “Jack, you should have stopped if you thought she had feelings for you.”
I said, “I know, but what am I supposed to do when a girl shows up in my bed naked. I was single, she was single.”
Amy said, “Fine, understandable, but what happened with Tiffany?”
I said, “Tiffany hooked up with Rob again one day. Then, at the end of the blizzard she was back with Will. They ended up sort of dating for awhile, but she was not that into him. He was fucked up about it for a little while, but he is fine and has a different girl now. She and I are still friends and she is studying overseas right now.”
Amy said, “Well, now I know who she is. Jack, she is pretty hot.”
Sarah said, “So, she basically spent all week fucking the three of you?”
I said, “That is pretty much what happened. One day the streets were clear enough, we drove her back to her place.”
Josie said, “It sounds like Tiffany had a pretty good week. Mary, you mentioned you were interested in a spit roast. We might be able to do something about that…”
Source: reddit.com/r/Erotica/comments/vaq8ox/my_gf_amy_tells_her_friends_and_me_about_her_hot
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