My First Time With A Friend free porn video

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I have always been pretty shy. I open up among friends but even then I still hold things back. I am not sure if it’s a lack of confidence or if it comes from me not knowing what to say. Knowing this, I figured it would be quite some time before I let some completely see me, mind and body.

I moved away from my hometown right after I graduated and hadn’t been back in a while. I missed my friends there so I took a weekend off from work and decided to go visit. I was excited to see everyone, especially one person in particular. I won’t give a name, nor pretend to make one up, since it would be easier for me to just refer to him in third person.

We dated about two years ago and remained close friends even after breaking up. We flirted constantly even though we both dated other people. My senior year I gave subtle hints that I still had strong feelings for him, though he'd been dating someone for a while now. He caught on, I think, to the hints but it didn’t go anywhere. He wasn’t happy with his girl and was very vocal about it, and I can’t deny that I, slightly ashamed, thought about breaking them up.

Back to the present, he's still with his girl and still vocal about being unhappy. In fact, I'm pretty sure she knows it. We've talked occasionally since I moved, more frequently since I told him I'm going to visit. He's made several not-so-subtle hints about us hanging out for awhile. So, of course, the smart thing to do is to prepare myself just in case. I take extra care while shaving and pack my best underwear set, ‘cause really, I don’t own a real lingerie set, but I’m working on it.

So I visit my friends and I see him for the first time since I moved. He looks good. He got taller, which compared to me doesn’t say much since I’m 5’2. He looks just as handsome as before, maybe more. We exchange hellos, but then we just hug for a good minute, slightly rocking back and forth, which is what he normally does when he hugs. We don’t get to say much else and I only see him once more that day, but we make plans to hang out the next morning.

First off, I am nervous. We have a basic non-verbal agreement of what will happen. I’m prepared for it. I’ve thought about it a lot before even making real plans to see him. I am mentally and physically prepared for it. I am extremely nervous, though. It doesn’t help that, never having been to his house before, I get lost. I suck at directions, and he gives crappy ones. After twenty minutes, I finally get there. I go inside and we go to his bedroom. I don’t say much and neither does he. He finishes playing a video game for awhile while I tease him about how bad he is. I lay down on my back while he puts on a movie and turns off the lights.

At this point I am beyond nervous. Nothing happens for a little bit. He is lying on his stomach next to me. Then he turns on his side and looks at me. We talk, bantering back and forth, which is what we do most of the time. He leans in and we kiss. It’s a familiar kiss, full of memories and sweetness. He moves slightly on top of me, still kissing, then rolls so I am on top of him. For me, this is awkward. First, he is skinnier than me (not saying I’m fat but I’m no model, and have full curves), second, me being shorter, to get my waist even with is, it makes his face right between my breasts. He says he's comfortable, but it’s not for me. We kiss for awhile with some grinding, then I roll so he is back on top of me.

More kissing. He sits up and pulls me up so that my legs are wrapped around his waist. Again, more kissing. He takes off my shirt and bra and happily sucks on each nipple. Honestly, this does nothing for me. Yes I'm turned on at the time, but again, it’s just slightly awkward. I kiss his neck as he pulls away and takes off his shirt. I press my bare flesh to his and we grind.

He then leans me back and takes off my pants and underwear. He kisses me as his hand finds my wet pussy. He then fingers me and licks me. Now, he is not a virgin, but he has never eaten someone out before. I guess his previous girlfriends didn’t care for foreplay. It wasn’t bad for his first time and I, only having it done once before, am not in a place to really judge anyway.

He takes off his pants and his boxers. We are both completely naked. This is my first time seeing a dick in person; therefore it is also my first time giving a blow job. I basically just try to do what I’ve seen on porn. It’s not as bad as I thought it would be (although I do end up gagging since he’s pretty big) and he seems to enjoy it. He groans so I take it as a good sign.

When I pull away from him, he lays me on the bed and puts a condom on. To me this is entertaining because he gets shy and tells me not to look. It makes me feel better to know he’s just as nervous as I am. He gets on top of me and asks if I’m sure. Too nervous to speak I nod. He slowly slides his dick into my virgin pussy. I won’t lie, it hurts. I have masturbated with a brush handle a few times before, but that doesn't prepare me for the real thing. And he's not even completely in! He gently thrusts in and out a little and I can’t help but whimper. He apologizes and asks if it hurts too much. I say no and he tells me he is going to push all the way in. I feel a hot pain in my pussy.

He gently continues to thrust in and out and the pain dies to discomfort. And then it hits: pleasure. A moan escapes me as his thrusts get harder. He moves my legs so that they wrap around his waist. He groans as he pushes deeper inside of me. I feel like I’m losing my breath and I start to pant as I moan. He stops so he can pull out as he cums. (I asked him to as a precaution.) 

He lays on his back and puts me on top of him in the cowgirl position. I immediately don’t like it. To me it’s awkward and his dick isn’t inside me enough. We switch positions again so he is on top and thrusting hard. My hands explore his back, pulling him closer and holding him there.

I alternate between panting and kissing him. His kisses are as deep as his thrusts. It feels so good, so warm. He pulls out again as he cums and I move off of him to lay beside him. It takes awhile to get my breath back. I turn to look at him.

We both just stare at the other for awhile in a comfortable silence. We then lay together and talk for an hour about absolutely nothing.

I enjoyed my first time with him and hope there will be more to come.

- - - - - - - - - -

This story is completely true, full of awkward moments and some not always erotic ones. But it is sweet (in my opinion) and hey, not everybody’s first time is a perfect haze of lust right? (As a side note, we were both 18 and 19 at the time.)

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Friday night had arrived and as usual, I was at the sex club early to assume duties as a greeter for any first-time visitors. Quickly, I changed into black latex shorts and a pair of black boots ready for the night to begin. After setting up the equipment in the dungeon I returned to the bar waiting for the guests to arrive.Slowly the room began to fill with the usual mix of friendly faces. By now I was well known to the clientele and almost everyone greeted me with a hug, handshake or kiss. As...

BDSM
4 years ago
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Summertime Fun0

Summertime Fun After my divorce I got my daughter every other weekend and for the entire summer. Now that she was fourteen and developing quite nicely I was enjoying her even more. I also indulged her desire for sexy revealing clothing, since her mother wouldn’t. Holly was pleased that I had purchased a summer home alone the beach. We used to go to the ocean when we were still a family. Another thing that I did to piss my wife off after the divorce. It was a very nice place and I...

1 year ago
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Summertime Chapter One

Summertime: Chapter 1 By Tommie Summertime, and the living was easy. I had just graduated college and I was home for the summer. My parents were on vacation and I had the house to myself. I had settled into a relaxed routine. Up late, lazy breakfast, a little bit of work on the computer to keep my hand in for the programmer's job I was starting in the fall. Then, as often as not, a lazy afternoon reading in the back yard before soccer training in the evening. Soccer had paid my...

3 years ago
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Club Orb First Timers

This is my third transformation story but my first straight up transgender romp. I'm a fairly new author and I'm striving to improve. Hopefully the story will be enjoyable and thank you for reading. Club Orb: First Timers "C'mon! Please come to the club, I know it's not your thing but I swear you'll have a lot of fun. My personal guarantee -- we will both get laid." Danny attempted to bribe his extremely undersexed buddy Jack. "That's... not really something you can...

2 years ago
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Facetime Accident With Mother In Law

Facetime Accident With Mother In LawIt was the usual time me and my girlfriend would facetiming but I felt a little risky this time so I was already naked. I gave her number a ring and had the camera straight at my junk trying to throw a little surprise there for her. I was swaying it back and forth and I still didn't get a reply. All I heard was.. “Uhm... Hello...” Next thing I noticed it was my girlfriends mom. I said oh shit and struggled trying to hang up while she said “No no... don't hang...

2 years ago
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TimeLine chapter 1

Like Billy Pilgrim, John and Amy have become unstuck in time. Unlike Billy Pilgrim, theirs is a fate more akin to eternal recurrence. Fate, for sure, had intended more for them. The timeline was diverted and the two were paying the price: Amy for her stubborn obstinance; John for his arrogance. For her stubborn behavior, Amy was dealt a hand similar to that of Sisyphus. She was placed upon life's treadmill: forever struggling to make ends meet; forever struggling to find her way...

3 years ago
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TimeLine chapter 2

When did the first, unfortunate fork in the timeline take place? Each attempt to divert the timeline back onto its true, fateful path has resulted in failure. Time is growing short, and an altered fate nearer. Each manipulation has resulted in this fate's end time grower slightly nearer or farther, but no significant change has occurred. Given that recursion is the problem, perhaps it is also the solution. Perhaps. The two share a weakness -- each knows on some level what needs to...

2 years ago
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Playtime With A Sissy Part 1 How I First Started

Playtime with a Sissy - Part 1 How I first started By Lisa Jade I enjoy dressing men up in sissy clothes. I suppose "enjoy" is not really the right word to use, as for me the experience is very much an absorbing sexual adventure, to which I have now become totally addicted. I know that I get just as much excitement and stimulus from our sessions as my poor sissy does. In fact I usually end up being wetter and in a bigger mess than he is. So let me take you back to when I first...

3 years ago
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A Night of Firsts

I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica.So after a lot of planning over several months, the day had finally come.I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth. I stepped out of the bath as Jessica and dried myself off. I wrapped the towel around myself just like any...

Crossdressing
4 years ago
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First times with the best friend

Mia and I study together at the college. We came from the same town, started our studies together, but we do have different fields. She is reading biology while I'm majoring in economics. Originally, we planned to be roommates, but Mia's boyfriend moved with her when we our school began. She has already left the bastard, but she decided to stay at their row house apartment. She was able to afford it. It's an early Friday evening. I'm just about to arrive at Mia's place. I promised her to...

4 years ago
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A Day of Firsts

A Day of Firsts by Kathy Nelson [email protected] (c):Kathryn Nelson, 1998 It was one of those hectic work periods where I was putting in 70 to 80 hours a week. You know, when there's no time for anything else in your life except the job. But, thank god the rush was over and it looked like things were going to calm down. Friday night had come around and I was going home at a decent hour. I even had the whole weekend off and I was ready to celebrate. Well, more like...

1 year ago
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Timeless Beauty 2

TIMELESS BEAUTY 2 BY PAUL G. JUTRAS Alex walked from the shower trying to dry his long shoulder length hair. In only a bath robe, he entered his college dorm room and turned on the television. The channel 5 weather man was giving a major warning for its forecast. As a transsexual he was happy to of gotten a single room. "This just in," said the weatherman. "This looks like it will be the worst hurricane season for Florida since the 1960s. The major threats are the hurricanes that...

3 years ago
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Sex With Schoolfriend

Hi, this Rajendra , 28 from hyd. She was my schoolmate till tenth class. Recently there was programme sponsored by our company in the city for a cause and I was one of the representatives from my company for that event. It was in the evening time that particular day there was rain in the city, so I took my car. There at the venue I see a class mate of mine standing at the stall put up by their comp as they were also sponsors for the event. Initially, I was not sure if it was her. Anyways she...

4 years ago
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Awesome Threesome With Two Bestfriends

Hello friends my self sanjubaba. I am 23 years old. This is my first​ story on Indian Sex Stories. For feedback and any girl or aunty wants to have fun mail me at secrecy is guaranteed. About my self I’m 23 year old single guy who enjoys and obsessed to sex.i can satisfy a girls and aunties with my 6.5 inch tool. I live in ahmedabad. Girls and aunties from ahmedabad as well as from other city can contact me for sexual fun. so coming to story during my college time i had many friends who were...

2 years ago
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An Afternoon of Firsts

The bar was crowded for the big football game. Standing room only. I was alone but hoped to find another regular to watch the game with. I ordered a beer and resigned myself to a disappointing spectacle. A good game was much more enhanced when watching with a familiar face or two. Halfway through my beer, I see Jim walk in. Jim was a guy a frequently chatted with and we really hit it off. He was the perfect guy to watch the game with. I flagged him over, shook hands and told him "Looks like...

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