How old were YOU your 1st time ? When did you have your "BIG O"?

[GMTA]

This series of events took place when I was a senior in high school. I was the ultimate geek. I was taking all of the honors program math and science classes and getting straight “A”s. I never went on dates or even held a girl’s hand let alone kiss her.

It was late October when Wendy, one of the cheerleaders, stopped me in the hall to ask if I would be interested in tutoring her in math. This would be on Saturday afternoon and her parents would pay $25 per session. Now I could use the extra pocket money for a computer system I was planning and since math was my best subject I agreed.

It should be mentioned that Wendy was one of the hottest and prettiest girls in the senior class. From the small amount of gossip that I heard among the guys she was a cold fish and a prick tease. None of the jocks that took her out ever got past a simple good night kiss at the front door but I never even considered anything more than helping her with the math problems.

Plans were set for me to come over to her house at 1:00 on Saturday afternoon to prepare for the next math test. What I did not know at the time was that she was an only child and her parents did not get home from their work until after 6:00 in the evening.

At exactly 1:00 I rang the door bell and wondered how long I would be collecting this added income to my computer budget. Wendy opened the door and invited me in. She said that we would be working in her room, upstairs. I followed her up the stairs without much thought to the tight “T” shirt and Daisy Duke shorts she had on.

We entered her room, which had a large computer desk on one wall and a queen size four-poster bed. She said, “Have a seat on the bed while I arrange my work space.” At this point I became a bit nervous and she seemed to sense it. She pushed me on my chest and said, “Relax, I won’t bite.”

I fell backward on the bed. At this point three other girls appeared, pulled me up to the head of the bed and attached handcuffs from my wrists to the bedposts. I was spread eagle on the bed with the entire four girl cheerleader squad in the room. Without saying a word they undid my belt buckle and pulled down my pants and boxers. My shoes were pulled off and there I was nude from the waist down.

Samantha, the captain of the cheerleader squad looked at me in all my glory and announced, “See, I told you ladies he had the right equipment.” Turning to me she said, “We have done some discreet research and the word in the boy’s locker room is that you have the biggest cock in the senior class.”

With this announcement they began to remove all of their clothes. Here I was, handcuffed to the bed, nude from the waist down and the four hottest, sexiest girls in my senior class were nude in the room with me. As can be imagined my cock began to get hard. I had seen pictures of nudes in Playboy and Penthouse but never live nudes.

I had the normal hormone development and was not a stranger to Rosie Palm and her five sisters but this situation got my cock very hard very quickly. At that point Patty pushed a pill into my mouth and said, “Swallow this”, as she held up a glass with a straw for a sip of water. As I almost choked swallowing the pill I asked, “What was that?”

Samantha broke in with the explanation. “We are all virgins and want to learn to fuck on our terms, not in the back seat a car with some club fisted football player. We have picked you to break each of our cherries today. Patty just gave you a Viagra so you will stay hard for each of us.

I see your cock is responding well so just relax and enjoy the ride. I should also say that we are all 18 year old virgins so there is no fear of stat-rape or STD, and we have all been on the pill for more than six months. We know you are over 18 and suspect you have never had sex so there is no need for condoms. We cut cards earlier to decide who gets to fuck you first.”

She continued, “OK Kate, he is all yours.” Kate was the smallest of the group. She was the one at the top of the pyramid and the most gymnastic of the group, in other words a real hard body. At 110 pounds she had a perfect set of “A” cup tits, small but perky.

Patty handed Kate a bottle of KY Jelly. My steel hard cock was coated with lube and Kate stepped up on the bed to straddle my hips. She started to squat down as Samantha held my cock up to Kate’s cunt. I had no idea what to expect and now I imagine neither did the girls. Kate started to lower herself onto my cock. She was very excited and breathing heavily as my cock entered her cunt.

She started to cry out and lift off my cock as Patty and Samantha grabbed her shoulders and impaled her on my cock. I was totally inside her before she had a chance to change her mind. The pain of ripping her cherry was immediately replaced with the shudder of orgasm. I had no idea what had happened except that my cock had never felt that way before.

The look on Kate’s face went through several changes in the next few seconds as the feelings of having a large cock buried deep in her cunt registered in her brain. She wanted to scream and cry from the pain of her cherry being ripped but the intense pleasure of her first orgasm replaced that feeling in a second.

She started to rock back and forth working my cock like a pro. She started to lift off my cock and then drop back to get the full length inside her hot cunt.

All of this time I was trying to collect the feeling I had, as her hot cunt would squeeze my throbbing cock. This was nothing like jacking off. I could feel her muscles milking my cock as I watched her firm tits dance before me. Then her breathing changed and the expression on her face changed. She fell forward, catching herself with her hands on my chest.

Her clit rubbed against the shaft of my cock for a brief moment and then she let out a loud moan as her body began to shake. Her cunt clamped down on my cock with greater force. She leaned forward and whispered in my ear, “That was wonderful, let’s do it again, soon.”

With that Kate lifted off my still hard cock and, turning to the other girls said, “Next.”
Patty stepped forward and Kate offered her the bottle of lube. As she crawled onto the bed she said, “I don’t need any of that shit. My pussy is soaked just watching you get the first fuck. All I need is that big cock inside me, NOW!” On her knees Patty worked her way up my body, lifted my cock and impaled her hot cunt on it without hesitation.

“Oh my God! That hurts so good,” she moaned as my cock slipped all the way into her hot, wet cunt. This time I kind of knew what to expect and felt the resistance of her cherry as she pushed to tear it. The brief orgasm she felt as she took my cock in flooded over the pain of breaking her cherry. She rocked back and forth on my cock, setting up a smooth rhythm that was causing the pressure to build in my balls. In a short time I felt that I my balls were about to boil over. I said, “If you keep that up I will shoot my wad right into your cunt.”

She replied, “That is what I want. Fill me with your hot sperm.” As I shot my wad deep in her cunt the pulsing of my cock sent her over the edge. Patty’s climax was even more intense than Kate’s. Her body stiffened and then broke into quivers as she screamed, “Fuck me you stud. I want it all. Oh GOD I want it all.” She then collapsed onto my chest.

As we calmed down Samantha said, “I hope there is some left for me.” I then realize that all the time we have been fucking, Samantha and Wendy had been standing there fingering their clits and pinching their nipples.

Wendy had been back, away from the action just watching the show. “OK…now it’s my turn and I don’t need any of that lube either. You sure know how to make a ladies pussy quiver. The juices are running down my leg.”

Wendy straddled my hips and lowered herself onto my raging cock. As my cock entered her cunt she felt the pressure on her cherry and screamed, “Hey, this hurts!”

Patty and Samantha grabbed her shoulders and shoved her down on my cock just like they did to Kate. Her reaction was different though. Wendy screamed at the pain for a second and then the intense pleasure of having her cunt filled with my hard cock set in and she had her first top grade orgasm.

She had climaxed many times from playing with her clit but those were nothing like the cunt full of cock climax this time. She arched her back, stiffened her entire body and her eyes rolled back in her head. Her cunt clamped onto my cock like a death grip.

Once she recovered from her initial experience she shouted, “Fuck me you magnificent stud. Fuck me long and hard. Fill my hot cunt with your jizz.” She started bouncing up and down on my cock like a woman possessed. She kept this up for more than five minutes and then enjoyed an even stronger climax. I was almost afraid that she had bent my cock. She then collapsed onto my chest much like Patty.

When she finally rolled off I spoke up. “Ladies, this has been some workout so far and Samantha still has not had her turn. Could we take a short break to let me rest and take off the handcuffs? I promise to be a good stud and not run away.”

With that Samantha took the key from the nightstand and unlocked the handcuffs. “OK..now you can play with my tits. I want to know how it feels to be sucked,” she said as she stuck her tits in my face. I took a handful of one and began sucking the other. Before this I had never even seen a set of tits in the flesh and now I was fondling and sucking the most sought after set in the entire school. Her tits were the biggest on the cheerleader squad and she was not bashful in presenting them for all to admire.

All of the previous activity and this tit play just added to the Viagra affect. My cock was so hard it hurt and it must have had the same affect on Samantha. Her breathing became heavier as she straddled my hips and started my cock head into her cunt. “This is your last cherry and you better be good. I want a cunt full of cum just like you gave Patty. I won’t quit fucking you until your balls are drained.”

Samantha’s cherry was the toughest of the group but she did not back off and my cock held up to the pressure. As the cherry popped she let out a gasp and drove her hot wet cunt down the full length of my very hard cock. Feeling quite confident at this point I said, “There, does that make you feel like a woman now?”

Samantha’s reply was true to her personality, “For a geek you are one fucking stud. I still demand that shot of cum in my cunt.” She continued to pump my cock as I squeezed her big tits and pinched her nipples. Since I had just unloaded one shot of cum into Patty it took a while to reload even with the hot Samantha riding my rod.

The ride was well worth it because she enjoyed several minor climaxes along the way. Thanks to the Viagra and my hormone level my cock never softened though. In due time I started feel the cum boiling in my balls and Samantha must have felt it too. Her breathing changed and her cunt started to grip my cock even harder. She leaned forward and moaned, “I am cumming right now!”

With her cunt milking my cock that was all I could stand. Her climax drove me over the edge. I pumped four or five loads of cum into her cunt. With all the cunt juice she was making added to my cum shot the mix was leaking down my balls. I wrapped my arms around her as we both collapsed in an exhausted heap. Kate, Patty and Wendy all climaxed at the same time from fingering their clits. The room reeked of raw sex.

After we had recovered Samantha continued her explanation of their program. “Patty and Kate have figured out the passwords to their fathers computers and have accessed the sex sites. We have been watching many sex acts that we want to experience but we need a well endowed stud to make them happen. This stud must be smart enough to appreciate the opportunity and learn along with us.

You seem to fit all of the requirements. We will meet every Saturday to experiment. Now that you have been initiated are you game?”

All I could think was, WOW what a ride, but then the naive side of my brain kicked in and I asked, “But what about Wendy’s math problems?”

They all laughed and Wendy explained, “That was just a front to get you here. I have been missing one or two problems on each quiz this last month just to build the need to get you over here. My speedy recovery will just further the justification for more tutoring.”

[TexAss]

Wow, don't know how the hell I can follow GMTA but here goes.

I was a 14, a freshman in high school, she was 17, a junior. She moved to our school and knew nobody, I was nice to her. She asked me if I wanted to go to a movie, even picked me up at my house. We never made it to the movie. She fucked my brains out and then dropped me off at my house. I never went out with her again, but was more than okay with it. Turns out she had a serious older boyfriend and just wanted some strange.

[sirliamscross]

My first "O" was a wet dream. No shit. What a mess. It woke me up and I actually thought something was wrong with my dick... HA HA! I was 14

I actually lost my virginity at 17 to a girl I had been dating since we were 15. It was all very sweet with lots of kissing and holding hands and me whispering "Are you sure?"

It is actually one of my fondest memories and I have shared it with my SO and even she thought it was sweet.

[OneFunGuyInDallas]

Ok... The first time I had sex was when I was 12, but since I wasn't physically mature enough to actually orgasm i don't really consider it as loosing my Virginity..Fast forward a year when I was thirteen and it was was one of my school teachers, she was I think 23 years old and it continued on for years after that and through many wild and crazy threesomes foursomes and moresomes. Cause you know I could leave my fellow brothern behind...and she was more than willing to oblige us youngsters. ..We occasionally still talk to this day.. Terrific lady whom I owe a ton of knowledge to...

[Kaci Snow]

OH wow thats all i have to say.

[shortstroke]

My first time was with a provider in LA. I was 18 at the time and got sick before it was my time. Her name was Sharmain(sp). I remember it lasted all of a minute; I stuck my pepe in and did two pumps and it was over. I've been hobbying ever since.

[vantruck]

Originally Posted by PoppyToyota

Shoot I didn't know about flogging the dolphin till I was 12 or 13? Found out by cleaning the loaded weapon without the safety on. Damn thing had a hair trigger....

+1

[Jima25]

I was around 11 my first o...like many others I found out by cleaning a loaded weapon. Was 18 when my first time and I got the girl preggers...loaded weapons are dangerous.

[MustangRider]

What kind of pervert screws a 12 year old

[Jasser]

My first experience, with someone else in the room, was when I was 14. I was a late bloomer, or my buddies were just flat fibbing about losing their virginity.

I was with my high school sweetheart. We were together for three months when she told me she was ready. She was at her cousin's house, alone, and asked me to come over. There wasn't anything romantic about it I guess since it was planned, but I remember thinking "damn, this shit is better than jacking off", lol.

We were both nervous and she did not have the big O the first time, but did the second time we did it. After that, we were fucking machines! I remember sleeping with almost all her volleyball friends, some of her basketball friends, and whoever else fell for my charm.

Those were some good days! I wish I had a fraction of the ass I used to get back then!

[devour]

16 and it was a complete spur of the moment with some friend of a friend. Not her first time so I expected some better, it was horrible and I think I could have gotten better from my hand. Actually I know I could have gotten better.

[Kaci Snow]

Guys these are some amazing stories. GMTA that was the best .. I felt like i was there you are an amazing writer.

[Guest101610-2]

I was 4 years old (though I didn't know what an orgasm was.) I discovered the joys of climbing things close to center mass. Doors were my favorite.

[Fiero]

I'm glad Kayla posted 4 for "O" because that's my answer including not knowing what they were but doing it OFTEN. Early fantasies were not sexual but more adventure oriented...like the cliff hangers in the old Batman TV series...lol.

Then for virginity...NINETEEN!!! lol Well if you've been having orgasms since you were 4...what's the big deal. I was "saving myself" for marriage as I was raised to do...then started dating my Dad's Secretaries daughter who was VERY experienced and after I said no to sex at the end of a date..she was shocked and asked why...I said, I'm a virgin and her eyes lit up like it was Christmas. I was raw meat to a lion and had no chance. I lasted exactly 22 more hours and it was a GREAT experience. Every guy should get to start with a woman who knows how. The following week she gave me my first BJ while driving. I really should have married her...LOL It felt very scandalous at the time...

[LuckJack]

When I was a freshman I played on the varsity football team, it was Christmas break and a bunch of us were hanging out at one of the guy's house. He had a sister who was home from college, probably 19-20. The older guys went to get beer and she came home a little high. She was my first, I was still 13.

Flash to this Spring. My cousin's wife passed away, he is 6 years older than me. I walk into the visitation his sister my other cousin is sitting there talking to an attractive older woman. My cousin asked my if I knew W....., she grew up in the neighborhood. After about 10 minutes of "did you know so and so" we realized she went to school with my cousin, the reason she was at the visitation. Then she says "you must have went to school with my little brother G.......

My jaw dropped to the floor and she turned crimson.