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Graduation Weekend

Category: Anal Sex
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I was heading to pick up my wife’s cousin since she was catching a ride with us. My sister-in-law was graduating from grad school this weekend, and I had to drive 4 hours up, hang out with in-laws, and drive four hours back. Not looking forward to a shot weekend.

I pulled into her driveway and gave the horn a honk. Emily came out and instantly I saw another piece of torture this weekend.

Emily just turned 21 and goes to the university here in town. She was wearing a tight blue V-neck t-shirt, and tight jeans. My wife and I enjoy a healthy sex life. We’re both 30, professionals, and fit. I’m happy with her emotionally, as well as physically. She’s tall at 5 foot 10 inches, thin, and blond. That is my favorite body type on a woman, but sometimes a girl like Emily just looks tasty.

Emily is the opposite type of sexy body. She’s not short, but medium height. She has long brown hair and wide, sexy ‘I want to suck your dick’ eyes. She has a great set of tits that were really accentuated in that blue V-neck, and a perfectly curved ass.

I was picking Em up on my way home from work, so I was alone in the car. She dropped her bag in the back seat and jumped in front. I could see her tits jiggle as she sat down in the car, and the v-neck showed some great cleavage.

We picked up my wife at the house and off we went. The drive would have been pleasant, but I couldn’t stop thinking about Emily’s tits. I look in the rearview mirror, those tits are there. We stop to eat, those tits are sitting across from me. My wife doesn’t have large breast, she’s the tall slender type, so I occasionally think about the pieces I don’t get.

Me, my wife Katie, my sister-in-law Laura, and Emily went out that night. Katie was getting pretty drunk, which I took to be a good sign. Usually when she gets drunk, she wants to fuck no matter whose house we’re in, so I was looking forward to a good way of working off all of the sexual tension I had built inside myself this weekend. As we went to bed, Katie was kissing me and I slipped a finger into her pussy. I talked softly as I fingered her and she was dripping. I tried to get ready to enter her, and she stopped me. She didn’t want to have sex at her sister’s place. She passed out shortly afterward.

I was lying in bed. Rock hard. Sexually frustrated. I tried to put it out of my mind and get some sleep. At about 2:30 I woke up and needed to go to the bathroom. I searched around for my boxers and could only find my t-shirt in the dark. I knew everyone else was asleep, so I just grabbed that in case I needed to hold something in front of me and went to the bathroom.

After relieving myself, I washed my hands looking at the giant mirror above the sink. I thought about how I was looking good. I saw my cock and it still looked a little swollen from the lack of relief. I thought about Emily sleeping in the living room and all of the comments she had made this weekend. What I wanted to do to her made my cock twitch a bit, but I thought jerking off in my sister-in-law’s bathroom was a bit too creepy, so I just went to go back to bed.

When I opened the door of the bathroom. Emily was about four feet away walking towards the bathroom. She was wearing some old short basketball shorts and a raggy black t-shirt.

“Shit! I’m sorry. I didn’t think I would see anyone on my trip to the bathroom.”

“Are you not wearing any pants?”

“No, like I said, didn’t think I’d see anyone. I thought I’d be safe walking the 10 feet to the bathroom.”

“Well sorry to embarrass you. I hate to make it worse, but are you a bit stiff under that balled up t-shirt?”

“Shhh… People are sleeping around here!”

“You’re right we cant have this conversation in the hall” Emily said this as she walked towards me entering the bathroom with me. She closed the door behind her and repeated. “So? You a bit uncomfortable?”

“Yeah, for a couple of reasons. One, I’m nearly naked in a bathroom with my wife’s cousin, and two, well, I didn’t get the sex I was hoping for tonight.”

“Nearly naked? You have a t-shirt balled up in front of your dick. I don’t think that counts as clothes. You’re naked.”

“I guess so. Well I assume you have to use the bathroom, so I’ll see you in the morning.”

“Hold on. What are you packing under there? It seems that Katie has the perfect man. I figured there had to be something missing, like you have a small cock. That doesn’t seem to be the case now though. Let me see just how big it is.”

“Not a good idea. You’re my wife’s cousin, and she’s sleeping 15 feet away.”

“I just want to see it, besides you said she’s passed out. It looks impressive.”

Emily was playing into my ego. I know I have a decent sized cock, but I still like to hear a woman’s opinion. I haven’t had that chance in years. I threw the shirt on the sink and showed her my semi-erect cock.

“Wow, it’s already pretty big. How big does it get when it’s fully hard!” With that, she reached down and started stroking my cock.

“Look, don’t touch!”

“Comm’on! I just want to see how big it’s going to get. Besides, you said you were frustrated. Let me ease your frustration.” And she put her mouth over my cock.

“Mmmmm…” she hummed as she worked her lips up and down my shaft. I reached down to start pulling her shirt up over her head. Emily paused from the blow job so I could remove her shirt. As it was her night shirt, there was no bra beneath. I stuck my dick between her tits and started to rub. She pushed those beautiful C cups together and I just stroked between them. Emily looked up and smiled with that devilish grin of hers and put her mouth back down to kiss the head. I knew I would come soon and asked her where she wanted it.

“I’d hate to make a mess, so how about you just cum in my mouth?”

“Sounds good to me,” and I stuck my dick back down her throat. Emily worked hard to get as much as possible down her throat, but could only fit about four of my eight inches in her mouth. I grabbed her hair and pulled her further down to get another inch or so down her throat just as I was about to cum.

“uuggghh… ulllggg… hlllggg…” She started to gag as I shot a huge load right into the back of her throat. I pulled out and let Emily catch her breath. After she did so, she reached back over and gave my dick a final suck to clean it off. She gave it a kiss.

“Sleep well, cuz!”

Chapter 2

A good blow job is generally better than any amount of Valium. Emily, my wife’s cousin, had just given me one of the best blow jobs of my life about 20 minutes ago, and now I was laying in bed next to my passed out wife trying to get to sleep. Problem was, this time the blow job didn’t get me relaxed for sleep, but just worked me up more. I laid next to my passed out wife with an erection that just wouldn’t go away. I began stroke my cock slowly. It just didn’t feel right. In part because I was in my sister in law’s guest room, next to my sleeping wife, but more so because after a warm wet mouth with a talented tongue, my dry work-worn man hands are a pretty poor substitute. As I lie in bed, I began to figure Emily must be worse off than I was. She didn’t even get off during our encounter in the bathroom. Maybe talking through our ‘issue’ would help me settle my mind down a bit. I decided to check on Emily to see how she was doing after our little session.

As we were all staying at my sister in law’s apartment, Emily got the couch in the living room. I quietly stepped out to the living room to be sure not to wake anyone else in the apartment. As I neared the couch, I could here some soft moans.

Emily must have worked her self up sucking me off, because when I got to her, her eyes were closed, her legs were spread, and her left hand was inside the gym shorts she wore to bed. She hadn’t replaced the t-shirt I ripped off in the bathroom, so her tits where sticking up the way 21 year old tits do. They were big, and started to fall to the sides, but her tits were so firm that they stuck out over six inches in the airHer right hand was slowly massaging her tit. I leaned down and put a kiss on her hardened nipple. She gasped and opened her eyes as I switched nipples and started to lick the other.

“I couldn’t sleep. You got me so worked up, and I knew you didn’t get anything in return. That’s just not fair”

“I couldn’t sleep either. I’m thinking about your huge dick and can still taste the cum in the back of my throat. My fingers are more just torture down here than any sort of relief. I could definitely use some help.”

I went right for her those short gym shorts, pulling them down in no time. Once they were off, I was treated with a perfectly bald pussy, swollen from her excitement and fingers. Her lips were pink and puffy, and her clit was sticking out almost half an inch. I pushed Emily back against the chair’s arm and pushed her knees apart. I leaned between her thighs and licked her bald pussy. She said she got waxed on Friday morning after Katie had told her how much I love a hairless snatch. Did she plan something for this weekend? Is this why it was always Emily at the bar with my wife getting more drinks? I pushed those questions out of my mind and pushed my tongue as deep as I could inside her slit. I licked the left, licked the right, flicked up to the clit, and dragged my tongue up and down. I should have brought scuba gear I was down there so long and so deep. Emily used her hands to massage those perfect tits and pinch her hardened nipples. She had to put a pillow over her mouth to keep from waking the rest of the apartment.

Just as Emily was about to cum, I pulled my tongue out of her snatch and licked down to her asshole. I didn’t want her to cum too soon, but also wanted to continue to give her some intense pleasure. Maybe some that she hadn’t had before. She gasped and clenched, but didn’t protest. I went back to her pussy, worked on her clit, and again when she got close to cumming, I slid back down to her sphincter, this time pushing my tongue inside a bit. She clenched again at first, but relaxed after a second. I rimmed her asshole, licking the outside while occasionally probing the inside.

“Mmmm… that’s feels good, weird, but good. No one’s ever eaten my ass like that.”

“Never?” I asked. “I like a little ass play. I little tongue, some fingering, and I love to fuck some ass. Katie’s not big on it, so I only get to do it about once a year.”

“My old roommate Isabel used to try to put a finger in my ass sometimes, but I thought it was gross and made her stop.”

“Isabel? The blond? God, I’d have loved to have seen that. Maybe she knew some pleasures she wanted to teach you.” I stopped talking so I could go back to licking her clit, but replaced my tongue in her ass with my finger. She moaned as my mouth worked all over her pussy, but she clenched again as my finger went in her ass. She relaxed after a second, and let my slowly slide it in. I worked her up towards climax again and her body became more receptive to the finger that was now sliding in and out, fucking her ass. Since I didn’t have a condom, I knew I wouldn’t be able to cum in her pussy, this was a good sign that I would still be able to cum in her without any risk of pregnancy. I flicked her clit with my tongue and worked my finger in and out of her asshole. I was ready to get my dick wet again, and Emily was begging to get fucked. I put her on her knees on the couch so she was facing the back of the couch. I stood behind her slid my dick into her over heated pussy and she groaned.

“Gooodddd!! I’ve been needing that all night! Fuck me! Fuck me! Fuck me!”

I had already cum once from the blow job, and had drank a decent amount of booze that night, so I was in no worry of cumming too early. I fucked her hard with deep strokes. Pulling out all eight inches except the tip, then slamming all eight inches back in.

“You like that? What else do you want?”

“I just want you to keep fucking me!”

“There’s nothing else you want? You sure? I thought you might enjoy some of the other things I was doing earlier.”

“Yeah, you could do some of the earlier things too.”

“Tell me what you want me to do, and I’ll do it.”

“Stick your finger in my ass! Fuck my ass with your finger!”

I lubed up my finger again with her abundant pussy juices and slid it back into her ass. He sphincter clinched, again, indicating how tight her ass could be. The finger seemed to strike a nerve with her in a good way. Her pussy clenched on my dick, and she started to tell me she was close.

“I’m going to cum! Don’t stop”

“I’m going to cum too, but I can’t cum in your pussy. Put you fingers on your clit and rub.” And I quickly removed my dick from her pussy.

“What are you doing?” “Ohhh!!” I didn’t need to answer as I forced my dick into where my finger had been. Her asshole had never felt a dick before, and certainly nothing this thick. It took a minute to get the thick head past her sphincter. Emily started to whince, but I slowed down and helped her fingers on her clit and massaged her left nipple. I slowly worked a few inches of my dick into her asshole as she furiously fingered herself. I pulled out a couple of inches, and slid in a few more inches. After a few slow penetrations, I had over 5 inches in her ass. I couldn’t fit the whole thing in, but enough for Emily to feel full, and enough for me to feel great.

“Ooohh Goodddd! I’m cummmmiiinnnnggg!! I’m cumminng!! Keep fucking my asshole! I feel so full of dick right now!” Her asshole squeezed hard on my dick on my final push as she came, and on that I got almost my full eight inches into her ass. That set me off as well and I came the biggest cum of my life. Rope after rope of cum shot straight into her no longer virgin asshole.

As we caught our breath, my dick began to soften in her back door. I kissed her on the back of her neck and said good night.

“Sleep well. I’ll see you in the morning.”

I got up to go back to bed where my wife was sleeping. As I rounded the corner to go back to the hall, I thought I heard a creak in the floor, and may have seen the door to my sister in law’s room fall close.

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