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It's funny how fast we grow up. How many of us never have friends our own ages. It seems they are always older and more experienced. When I was a sophomore, one of my best friends was dating a senior boy. As a result, the gang that I hung out with was mostly seniors. One summer night, a group of about 20 of us were just hanging out and cruising. I had on a short denim skirt and a tight tank-top and was being a big tease.

We decided that we would go from the mall to a teen club across town. Derrick grabbed my hand and said we should ride over in Michael's car. Harold said he would also ride with us. So I climbed into the back seat between Derrick and Harold and off we went. We didn't get very far before Derrick was kissing me. He had a muscular build and dreamy blue eyes. Having him notice me was a dream come true, let alone to start necking with him. As we got going Harold started kissing my shoulder and neck. This was great! TWO senior boys interested in me. Derrick started to feel my tit. It wasn't the first time a boy felt me up and even if we weren't alone I wasn't going to stop this hunk. Harold was good looking also and not far behind Derrick in going for my tits. I turned my head to kiss Harold as he squeezed my tit and as I did he unhooked the back of my bra in one quick motion. Derrick and Harold instantly had my bra and tank-top up to my armpits and my tits out. That's when Michael reached back between the bucket seats and put his hand on my thigh. As he gently rubbed the inside of my thigh I resumed kissing Derrick. Harold moved down and began to suck my nipple. I had earlier thought about when I would have sex and was determined to fuck a guy by the end of the year. The right opportunity for a quiet romantic setting with a great guy just had not happened. While Derrick and Harold took turns kissing me and sucking my tits Michael was moving his hand further under my skirt. I soon felt his fingers pressing the material of my panties into my pussy. I moved my ass down on the seat to give him better access to it. As he slid his finger into the leg opening of my panties I reached for the front of Derrick's pants. I felt the bulge of his cock and gave it a squeeze.

Michael said, "Well guys, is our little Anna still a tease or is she a party girl like I said."

"I don't know what you mean by little," Harold said as he pulled his mouth off my tit. "There's nothing little staring me in my face."

"Just get back to her tit. I'm sure the lovely Anna is enjoying what you can do to a tit."

I sure was but my attention was being focused on Michael's hand. Other boys had put their hands on my crotch before and one even was in my panties. But they were all very clumsy and rough. Michael must of had a lot of experience as he knew what he was doing and made me feel great. My pussy was getting soaked and I kept moving my ass closer to his magic fingers.

Michael said, "She's really getting wet. A few more minutes and our slut will really be ready to party."

I was immediately offended by being called a slut but that is when Michael slipped his finger into me. I was totally distracted by that, I didn't care what he said as long as his hand stayed on my pussy.

"This is one tight, wet hole Derrick. You need to check it out." And Michael pulled my panties off.

Harold and Derrick started moving in the seat. Harold pulled my top over my head and laid me down across his lap. We were kissing deep as I felt Derrick between my knees. I was expecting his fingers and felt one slide up and down my pussy, getting wet. I remember thinking that Derrick had very big fingers when he pressed it against my cunt hole. Harold was playing with my nipple and I was enjoying the feeling of Derrick's "finger" against my hole when a sharp stab of pain ripped through my. I winced once and looked up a Derrick. That's when I felt both of his hands on my hips. As I looked into his beautiful eyes I realized that it was his cock inside me and he had just taken my cherry. I was in shock at first but Derrick started to slowly slide his prick in and out of me. I started to relax and move my hips with him. So this is what getting screwed was all about! I was loving it even if I still did have a little discomfort. Derrick started to pick up the pace and he was moaning on each stroke. Harold was still playing with my tits and I started to moan loudly...

Harold said, "Michael, how much longer? We really have this bitch in heat. Derrick will have her cumming in a minute."

"Just keep at her," was Michael's reply, "it'll be a few minutes yet."

Harold put his hand between Derrick and me and his fingers reached my clit. That put me over the edge. I started screaming "Yes, oooh yes" at the top of my lungs as Derrick and Harold brought me off. That's when I heard Derrick grunting and driving his cock deeper into me. I felt the warmth of his cum as he spurted farther into my cunt than anything had ever been. As Derrick's dick slid out of my wet snatch I got up to kiss him. As my tongue snaked into his mouth Harold got up on his knees behind me. When we broke the kiss Harold pushed me down on all fours. His cock was in my pussy in seconds. Derrick slide under me to suck on my tits while Harold took me doggie style.

"This pussy is going to take some real stretching Michael. I'm going to have to work on lubing her up some more." Harold was really pounding into me now. I could feel his balls slapping my clit as he rammed his dick into me. I could feel another orgasm approaching and this time Harold and I came off together. I was getting into the language these guys were using and was yelling for Harold to fuck me harder as I came. While I screamed, Harold grabbed my hips and drove his cock deep into me as he came. I collapsed at this point trying to catch my breath. Derrick began to rub my back and Harold played with my ass. I could feel that we were going down a dirt road.

When the car stopped Derrick and Michael got out while Harold continued to caress me. The boys opened the trunk and rummaged around a little bit. Derrick opened the door to help me out. There was a blanket spread out under a tree, candles were lit around the blanket and Michael was lying in the middle with nothing but his boxer shorts on. I stood up and pulled my tank-top and bra over my head. That left me in my skirt and sneakers. I walked over to Michael and asked him what was in store for me next. He looked up my skirt, reached behind my knees and pulled me down. I fell over with my tits hitting Michael in the face. His mouth went straight to my nipple and started sucking. Michael's hands slid up the backs of my thighs and he grabbed my ass. His squeezes caused my cum filled cunt to make noise.

Derrick said, "Michael, that tight, wet pussy is calling for your dick. You had better take care of it before one of us comes back for seconds."

Michael didn't say a word but slipped a finger into me again. I was getting real hot again and reached into his shorts. I couldn't believe what I felt. Michael had to be bigger than either of the other two guys. I started to panic. An hour ago I was a virgin and now here was a cock that I could barely wrap my hand around, getting ready to fuck me. What was I doing? But that finger was attracting my attention. As much as I was scared I was also very excited. Could I take him? Would it hurt? There was only one way to find out. I took a deep breath and pulled Michael's shorts off him. By the candle light I could see the large, mushroom head of Michael's massive cock. How could I get that into my little vagina? It was bigger than I could have imagined. Michael started to kiss me, putting his tongue deep into my mouth. His fingers caressed my clit and my juices flowed in spite of my apprehension. Michael was good with his hands and I could feel an orgasm building. I was straddled across Michael's stomach as he felt me up. Just as I was about to cum Michael gently guided my pussy onto his cock. I hardly noticed his entry as I came in a rush. Michael continued to push his cock into me as I screamed in ecstasy. As his strokes got deeper I came again. I had three orgasms right in a row as Michael reached his climax and came deep in my pussy. I collapsed on him, feeling his cum ooze out of my pussy as his cock got soft. Even limp it felt huge inside me.

XXXXXXX

As I lay there on top of Michael, Harold came up and carefully slid his hand between us and began to rub my clit. With the other hand he played with my pussy and got his fingers all slick with my juice and Michael's cum. That's when he began to play with my ass again only now his slipped his slick finger inside me. He didn't try to penetrate far, just to the first joint where he began to twist and turn his finger in my asshole. As strange as it felt it also felt very good and I moaned, pushing back against it. That was all the incentive he needed as he began to stroke deeper and deeper into my ass with his cum slicked finger. Michael began to kiss me again and Derrick was rubbing my tit. When Harold slid the second finger inside it hurt for just a second but it still felt so good I couldn't stop him. By now his rubbing on my clit had me close to another orgasm. Derrick stopped rubbing my tit and moved so I couldn't see him. Between Michael's kisses, Harold rubbing my clit and stroking two fingers into my asshole I really didn't miss him. Just as I was going over the edge Harold removed his fingers and they were replaced by something else which stroked even deeper into my asshole. Derrick's cock was hard once again and he was now fucking me in the ass with it and it felt GREAT! Pulling me back against his strokes by holding on to my tits Derrick started to pick up the pace. Pulling me up on all fours he pulled me off Michael's soft cock and when it flopped out even more cum trickled down my legs. Sliding out from under me Michael moved to the side so he could watch. Running his hand up my legs from in front Harold gathered some of the cum and rubbed it on his hard cock before using it to rub on my clit again.

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03.05.2021
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I have a new job working away and I bought an iPad to keep in touch with the wife, it’s great seeing her when away I miss her so much so it’s great when I’m bored in my room. Jane and I for years have spoke about sharing? But she never comes through, it must be 4 years now we have had the same conversation about it and it’s always the same answer maybe! Jane is great in the sack she knows how to please, I keep telling her she needs to give it out cos it’s going to waste on me as I only last...

Showtime for Teri

Showtime for Teri By Teri Franken Chapter 1 My name is Teri and I am 28 years old. I have been a closet sissy for as long as I can remember. My parents knew that I was not your typical child and they let me live how I wanted to and did not judge me, they just loved me unconditionally. I grew up loving everything that a little boy typically doesn't like, such as dresses and dolls. My parents were concerned that I would be a target for bullies, so I was home schooled, took my GED...

Eagle in the Sunset 2019Chapter 29 Summertime for Us All

October 17th, 1995, 7:30 AM PT, Metro Plaza Hotel, Los Angeles, CA Miriam had been tossing and turning all night; she spent time just sitting in the chair in the corner of the room to try and let Baruch sleep. She was so upset she was oblivious to the fact that Baruch couldn’t sleep either, which was not in her nature. She was usually fully aware of what was going on with her husband. They thought together almost telepathically, and yesterday had been one of the first times in decades when...

Timeless Beauty

TIMELESS BEAUTY BY PAUL G. JUTRAS Sam walked in the dorm house, looked at the lock and then in the dorm mistress's room. The plus size woman was dress in a black blouse and flats, black with white palm tree design jacket and skirt with dark brown nylons. She new there was only a half hour before she made her rounds and called lights out. Upstairs, roommates Chris and Alex waited on their beds. Like their friend Sam, both guys were petite and lovely looking. Being transsexuals who...

Younger Than Springtime

The door was open. I had no reason to have it closed. We were all in this together. So I was sitting in the large chair as my nurse prepared to access my port to begin the first liter of Cisplatin. The cancer center had been busy today and I glanced out the doorway as several people passed by. Then I noticed a woman pausing as one of the nurses escorted her somewhere.It was Katherine. I recognized her at once even though it had been so many years ago. Then I heard her laugh as her companion...

Mafia And The Journalist Of Seduction 8211 Part 7 Gangbang With Gangsters

Alisha pushed Arora and grabbed her white top then ran towards the back door. She pushed it open and ran outside when a car drifted and stopped right in front of her. “Who is this now?” she groaned. “Why are you always naked when we meet,” Nyla giggled unrolling the window of her black sedan. “Get in Dumbo, we have to escape” Nyla shouted again. Nyla was David’s sister but Alisha wasn’t bothered about that. To Alisha, saving herself was the most important thing right now. Alisha was seated at...

Master of All Timelines

Your name is Edward Richardson. You're 20 and you've been fascinated by history ever since you're 11. You're also good at making inventions as well. As you're growing up, you usually found that at various points in history of each country, things always turned ugly at many points. And you wanted to change that. You decided to use your intelligence you create the device called the T.O.S, abbreviated for Timeline Opener and Stopper, that can make you travel back in time and alter the histories...

First Time Sex With My Longtime Bestie

Hi everyone Akshay here, age 23 from Chennai. I’m a reader of ISS for the past 5 years, and it’s high time I shared my experience. This happened a couple of months back. It was with my longtime bestie. Her name is Vaishali. We know each other for around 6 years, starting from our college days. She lives half an hour away from my place. I’m pretty familiar with her parents. We got to know each other from our college days as we were from the same department. She had a sexy shape, which gave me a...

Ganged

All they wanted to do was to get out, but John, being in an argumentative mood, had began to argue, saying he would move it when he had finished his drink. Obviously this did not go down well with the guy and then his two mates came in and they said in no uncertain terms they wanted it moving now or they would smash their way out. In the end, after more harsh words, John relented and went out and moved it. Apparently when he came back in he said that there had been more harsh words in the car...

Debbie gets ganged

He met Debbie at his house; as per usual, his parents were out working until late that evening. They sat on the love seat in the living room and Jay was hotly kissing her swan-like neck while cupping and rubbing her big, bra-less titties through the tissue-thin fabric of her cut-off top. Her stiff nipples strained against the soft fabric, the round brown aureoles clearly visable through the nearly transparent material. Jay said “how would you like to suck and fuck a couple of guys that I...

GAIL GETS GANGED

My beautiful wife Gail and I were driving back from a trip to California last month when we stopped to stay at the Holiday Inn in St Louis. We got a room right off the pool next to the Jacuzzi. It was perfect. I opened a bottle of wine and got her a little tipsy before I showed her a thin white bikini that I had bought her in L.A. She protested that it was way too revealing, but I convinced her that the Jacuzzi was just outside our room and no one would pay her any attention. Man was I...

Violett 4 I Get Ganged

At the age of nineteen I left home for college and I really went out of control. I came out of the closet and immersed myself in the lesbian community. I was a big hit. There was a small lesbian tavern close to campus where I used to hang out. I was under age but I never drank anything so the management let me hang around. One of my first lovers there used to call me Angel, it caught on, and to this day I still have old friends that call me Angel. I was real popular too - women even fought...

I was a wartime TV for the US Army

‘I was a Wartime Transvestite for Uncle Sam! TJ Ryder Chapter 1 Reform School Romance! I couldn’t believe that all I got from my uncle Bill when he died after all he said to me about my being his favorite grand nephew was an old diary from World War II. I mean I thought we got along pretty darn good, and its not like he had any money or anything, just another old geezer in an assisted care center who if he ever had...

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