Hi there, I am Matt, the one who actually set up this account. A very close friend of mine, Linda, kind of got me started by offering to write a story that I submitted under my pen name, iamscrwd. Thank you Linda…you are so hot!!!
A little about me, I am, now, a married nineteen year old male that did not even lose his virginity until I was sixteen years old. Heck, three and a half years ago, I thought my sex life was going revolve around Rosie Palmer and five sisters, but that all changed when my mother, Kathy, and step father divorced right after my sixteenth birthday, with my mother moving my younger step sister, Katie, and I to a town were her sister lived. It was a whirlwind change as my mother filed a restraining order, got a legal separation, filed for divorce, and negotiated a final settlement, then moved during the course of a couple of months.
Katie, my half-sister, is about a year and a half younger than I and even then at fourteen soon to be fifteen, she had a great looking body. She started blossoming during her twelfth year and over the last couple of years her confidence grew into her being a constant flirt and tease to almost every male from thirteen to forty. Because of her extroverted nature, I pretty much followed her lead as we went through indoctrination at the new High School we both would be attending. Almost immediately, Katie struck up a friendship with an absolutely knockout of a girl named Jen. Jen is a fairly tall girl with a figure that any twenty something would die for. She possessed a rack that was at least a 34 C coupled with a 21” waist on a 5’6” frame and she was only fifteen…holy molly, almost wore out Rosie Palmer and her five sisters dreaming about her. Of course, I had to stay attached to Katie’s hip so my proximity to Jen would be close.
The week before school was to start, Jen called and invited Katie over to her house to go swimming in their pool. Of course, I asked if I was invited too, and received the ok. Katie donned a skimpy bikini that my mom gave her (even though I knew it was wrong, I now had a different scenario for Rosie and her sisters) and just threw a t-shirt over it. Not having a swimsuit, I just wore a pair of cotton gym shorts.
Mom drove Katie and I over to Jen’s, who met us in the driveway and led us to the pool as our mom drove off. Approaching the swimming pool, I noticed a woman with short blonde hair laying face down on a towel and from my perspective did not a have any clothes on. Jen walked right up to her and announced “mom, I want to introduce you to my new friends”. Holy shit, the woman just turned over on her back, peeked under her sun glasses and made absolutely no attempt to hid even one inch of the most gorgeous body I had ever seen, not even in magazines. My eyes tried to take in as much as I could; you have to remember that the only real female parts that I have seen were flashes of sister’s (her teasing) and mother’s (me peeping) parts. Laying on her back, her tits pointed straight up defying gravity with quarter size rings going through her nipples and scanning downward she had a pierced navel, a small barbell that held her clit exposed, and two smaller rings on each side of her smooth as a babies butt pussy. She opened her legs slightly and exposed her slit. I must have been gawking, because she had to say excuse me a couple of times while offering her hand to me to help her up. She stood up, faced me (she was at least 5’8” tall) and introduced herself to me as Linda, Jen’s mom and from my expression, that I must be a virgin. With that, she told us she had errands to run and would be back later that evening. She reached down and grabbed my cock through my cotton gym pants, then leaned forward whispering in my ear that it makes her feel good that a young man can have that kind of reaction to an old woman. She stroked my cock through my shorts a couple of times and then her nipple rings made contact with my chest. My cock involuntarily spasmed, as I shot my wad into my shorts. Then she walked away.
Katie looked at me, the wet spot in my shorts, and Linda walking into the house and said “wow”. Then she looked at Jen and started laughing. Jen looked at me with a crooked smile and asked “so, you really are a virgin aren’t you?” They both had a good laugh as they discarded their overshirts and jumped into the pool. Deciding that the pool was the best solution to my embarrassing situation as my cum was now running down my legs, I too jumped in.
As I was swimming, one of the girls swam underneath me and yanked my shorts off. Quickly turning around, there was Katie laughing and throwing my shorts to Jen, who promptly threw them out of the pool and over the fence. So, here I am naked in a pool with my sister and her friend thinking I will have to wait until dark to get out of the pool. Both girls walked out of the pool and without any provocation, took their skimpy swimming suits off with Jen asking if I will have the same reaction with them as I did with her mother. Jen stood directly over me at the edge of the pool and as I looked up, I saw that she had a very light wisps of hair above her pussy with a clit ring at the top of her slit, she had a piercing in her naval and one nipple ring in her left nipple. Katie walked up right next to her and I noticed she did not have a speck of hair anywhere on her body. Her tits were each the size of half a small cantaloupe with large red areolas topped by what looked to be quarter inch erasers.
Katie was really checking out Jen and asked her about her rings. Jen said that they really enhanced the sensitivity during sex (and here I thought that Jen was virgin…and hoped to be the one!) and go ahead feel them. Right above my head, Jen spread her pussy and Katie reached over with her thumb and finger then pulled Jen’s clit ring. Jen looked up into the air and sighed. Jen using her free hand moved it to Katie’s snatch and rubbed her cunt. Standing in the water underneath them, I stood amazed as Katie was getting Jen off and now it looked as though Katie was right with her. As Jen pulled, squeezed, and rolled Katie’s clit, it grew to extend about an inch from her cunt, then all of a sudden, Katie tensed, shook, and her clit looked like it ejaculated…right on my head! With that Jen stiffened, convulsed a few times and moaned loudly. Both looked at each other smiling, then sitting down at the edge of the pool, both wet pussies within inches of my face, they started kissing each other while fondling each other’s tits. This whole time, my cock had grown to its fullest extent, but I dared not touch it, as it would have exploded. Now that the expectation had passed, my cock slowly deflated.
As Jen and Katie regained their composure, their attention reverted to me. Jen asked if I enjoyed the show, of which I responded “yes, but I never would have guessed”.
Jen responded: “well, let us see what you have, or don’t you have balls?”
Katie answered; “I have watched him jerk off a couple of times (my surprise) and it is one of the fattest cocks I have seen (how many has she seen?), but I have never seen his balls”.
After the shock of being caught jerking off, I was now proud of my member and told myself what the hell…since they are lesbians anyways. I climbed out of the pool. Now, not having anything to compare it with, I still thought my cock was special. When completely flaccid, it is about the diameter of a fifty-cent piece and about three inches long, but it is extremely pliable to where my cock head (which is smaller than the shaft) can be pushed into the base of my cock…it looks as though I have a hole where my cock normally is. That, and my balls are real tight to my body. They have a seam that runs between them, but there is not very much separation and my balls do not dangle. When filled and hard they protrude more forward than down, looking like a peach cut in half and attached to my crotch from an inch and a half from my asshole to around my dick. I heard the Doc say once that they just never dropped, whatever that means. When my cock gets hard, it grows quite a bit to where half of it is above my belly button and at least a good seven to eight inches long, and I cannot get my entire hand around it, about the thickness of a beer can. The cool thing too is, when I cum, it unloads with so much pressure, I can jerk off sitting in a chair and hit the ceiling with my spunk!
So, getting out of the pool, my member was just being its normal self. Jen motioned for me to stand between my sister and her. Jen picked up the end of my cock and looked up underneath it, saying, “he doesn’t have any balls!” Katie reached over and grabbed where my balls really are and said, “no, they are right here, I can feel them” as she rolled my testicles back and forth. Jen mentioned, clinically, that she has never seen them like that, but maybe they would fill out more when excited. Well, I was more embarrassed than excited and my cock was trying to hide. Katie, started pushing on the head of my soft dick with her thumb and found out that she could push it inside out. She was mesmerized by its ability and continued playing with it until she had my entire cock shoved up and inside of me. With my cock now gone, she pinched what is the upper part of my scrotum together, completely covering my cock. Katie exclaimed, “ Look he has a pussy!” With that Jen told us to move to lounge chair so they could experiment. I felt like a guinea pig, but this is the first time I can remember female hands working on me, so what ever. Laying face up on the lounge chair, with Katie still squeezing my nuts together so as not to release my dick underneath, Jen stretched my arms over my head. This put Jen’s left tit less than two inches from my face, I could not resist, lifting my head I grabbed here nipple ring with my tongue pulling the ring along with her entire erect nipple and areola into my mouth and sucked. Jen attached restraints to my wrists, and then pulled up saying, “at least you have some instincts, nice tit isn’t it?” Jen’s next move was to secure my legs, tying my ankles together under the lounge chair. The whole time my sister still had a vise grip on my testicles, squeezing them together.
Satisfied with her confinement of me, Jen stood up and swung a leg over my head giving me a close up view of cunt, which was slightly open to expose her labia, and I could see her clit ring reflecting in the sun. Her slit was moist, with a small driblet running from the bottom of her pussy to her perfect rosebud of an asshole. Jen lowered her cunt to my mouth and told me to now do to her clit what I had done to her nipple just a little while ago. I could not resist, sucking her clit ring and her clit with as much force as I dared. Her pussy enveloped my nose and her asshole was just millimeters from my eyes. As this was happening, Katie, placed her mouth over where my cock was trapped under the folds of my testicles (she was calling it my cock hole) and in one solid movement, sucked the head from it’s prison into her mouth, then using her teeth while still maintaining suction, pulled my cock out like stretching an accordion. She quickly took as much of my cock into her mouth as she could as my cock filled out to it’s maximum size. I could feel both my sister’s hands stroking the sides of dick. Jen had started gyrating her hips and from the amount of liquid running out of her pussy was getting really excited. She said that my cock had to be one of the fattest she had ever seen while telling me to tongue fuck her pussy. I went from sucking her clit to sticking my tongue as far up into her gash as I could, lapping away at her cunt. I thought that I was going to drown from the amount juices that were flowing from her hole. My sister released my now fully expanded cock from her mouth and licked the shaft from my gonads to my pee hole, forcing the tip of her tongue into it. Katie then commented to Jen that she could not believe the size of her brother’s cock, that it was even bigger than that asshole Mr. Wilson’s (our fifty year old neighbor!). With that, MY SISTER, straddled my cock, holding the head against her pussy opening and slowly worked her cunt down around the head. This whole episode was just freaking me out! I was about to lose my virginity…to my little SISTER! Katie moved her cunt slowly down my shaft and even though her cunt was drenched, there was quite a bit of resistance. Finally getting past her pelvic bone, she dropped her entire weight on my cock, taking the entire dick into her vagina with the head of my cock pushing past her cervix. Katie gasped as she told Jen that she thought I was splitting her in two. This excited Jen, as her fluids ran unabated over my tongue and into my mouth so I had to suck and swallow the juices. Jen then slid her cunt over my chin with my tongue sliding from her pussy to her asshole. She then told me to tongue fuck her asshole. Without much resistance, my tongue forced itself past her sphincter and into her shit canal. Jen grabbed my nipples hard while twisting and pulling them while she drove her ass down over my tongue as far as it would go. This whole time, Katie was moving up and down my cock with her vaginal muscles now spasmodically pulling on the body of my dick. I could hear both the girls breathing heavy and gasping for air, while their movements became uncontrolled. Jen announced that she was going to cum and moved her cunt back to my mouth, telling me to open wide as this was going to be a big one. With that she jerked stiff, then moved spasmodically, while her pussy pulsated. With a big release of air, she flooded my mouth with what seemed like a gallon of hot, salty liquid. Simultaneously, electricity ran through my balls and cock, with the pressure building to the point of no return, my cock erupted squirting hard into the womb of my sister. With the first shot of my hot cum hitting deep into my sister, Katie exploded into an uncontrollable gyration with her cunt muscles milking my cock for all that it was worth. My cock let loose multiple strings of pulsating, forceful seed, than paused for a second and then let one more out.
Both Katie and Jen grabbed each other, sucking on each others tongues in a hard embrace. Because of the size of my cock and Katie’s pussy being stretched tight around my base, it felt as though my dick was trapped in a hot water balloon. The sensation of being in a cunt for the first time was so overwhelming that my dick stayed as hard as a rock. Katie mentioned that to Jen and Jen’s response was for her to fuck it next. Katie extracted herself from my cock, holding her pussy closed with her hands, while Jen slid down to my cock. As she swiveled to face me, she grabbed my cock with both hands stroking it. Then she placed the head of my dick at her pussy opening and lowered herself on to it, one inch at a time. She was much tighter than my sister and her cunt felt like it was on fire, but she managed to get the whole thing in right down to resting on my pelvic bone. My sister had by now regained her composure and moved to above my head, stilling holding her hand over her pussy, then said, “Since you are just learning, you might as well learn correctly…clean me out”. With that she straddled my face, pulled her hand away just as a glob of my sperm mixed with her juices landed on my lips. I had just enough time to see her stretched open pussy hole filled with the cream of my cock. She reached behind her ass, pinching my nose causing me to gasp and inhaling the glob of cum on my lips. Immediately she sat her cum soaked cunt right on my mouth and with a slight push from her vaginal muscle gave me a mouthful of my spunk. At first I was revolted, but after a few swallows and differentiating the taste of my cum to her pussy juice, I started giving her the same treatment as I did Jen. Jen by the way, was now bouncing up and down on my even more engorged member. Jen’s vagina had such muscle control that she would tighten up on the up stroke, stretching my cock at least a couple of inches more, then releasing it just quick enough that I would gain another inch or so into her womb. It did not take long for me to feel the charge in my testicles begin to roil. By now Katie’s pussy was spotless, I had sucked the living daylights out of her inch long clit, and she now had me eating out her asshole. Jen was moaning and groaning that she was ready to cum, Katie slipped her cunt back over my mouth, then both of them embraced as they came. That sent a signal to my cock, and for the third time today it unleashed a torrent of cum, this time into the deep recesses of Jen’s womb. Katie lost control, and came so violently that her bladder released, overflowing my mouth and running down the sides of my face. From the taste, I knew now that Jen had don the same thing when I ate her out. They both relaxed, Katie standing up, moving off my face while talking to Jen about what just took place as if I was not even there. Jen pulled my cock out of her pussy and slid her cummy cunt to my mouth nonchalantly telling me to clean her out. This time some of my cum missed my mouth and a goblet ran down the side of my nose and into my eye, both Jen and Katie just giggled. I proceeded to suck, lick, and eat all my seed out of Jen’s pussy while they talked about trying to seduce some older married guys with money. Jen looked down and asked if I had it all clean. I nodded my head the best I could with her cunt lips stretched over my face. She then said that she would rinse my spunk down my throat and this time try not to miss any of her pee. Immediately I felt a steam of hot, salty liquid surge into my mouth, I gulped and gulped feeling the hot liquid wash some of the stringy residue of my cum down my throat and into my stomach.
They both got up and walked away towards the house, completely ignoring me stretched, spread-eagled, and tied down outside by Jen’s family pool.
That is how my first day of loosing my virginity ended.