To start with, my name is Jay and my best buddy for most of my life has been Russell and this is about my 18th birthday. Well at least the celebration of it the weekend following my 18th birthday. As I was still in High School had to wait until the following weekend to whoop it up and that is just what Russell and I had planned.
So early Friday evening I drove over to Russell’s house to pick him up with plans for both of us to head up to my parents cabin for the weekend that was close to a small country bumpkin college town inundated with plenty of hot co-eds. Granted Russell and I were still in High School, but both of us being of larger stature, we could pass for college kids. Even though Russell was just a young pup of 17.
Arriving at the Wagner’s home to pick up Russell, I was met at the door by Lori. Lori is Russell’s 16-year-old sister that goes to the same school as we do. Lori is a very hot looking chick, and she knows it, teasing any swinging dick she comes across. She also has an antagonizing habit of putting me on the spot with her questions that should be private.
Lori of course was dressed to the nines waiting to go out on a date. She was wearing a slinky mid thigh length, low cut dress that accentuated her youthful figure. She had yet to fill out her chest, but still managed to have a cleavage with the help of a push up bra. Her legs were absolutely perfect though; from toes to thighs it appeared that they were off a well-formed mannequin.
Me being me, of course I tried to visualize what she looked like under her clothes. It helped as Russell and I a few months ago, were tasked to run to the local under garment boutique for Lori and Mrs. Wagner, to pick up a few items for them. Mrs. Wagner gave us instructions to give a certain attendant a card with Mrs. Wagner’s and Lori’s critical measurements in which the attendant could confirm the proper item was shipped. Of course we had to look at the card. It showed Lori being 5’3” to 5’4’ tall, weighing 110 lbs, with measurements of 34-22-34 and specified large A/small B cup. Now Mrs. Wagner’s critical measurements were 5’7’ to 5’71/2”, 135 lb, and having a 36-26-37 figure specifying a full C cup (nice to know, even though she was older, I did have more than one self induced orgasm thinking of her).
So, with me thinking about whether or not Lori had graduated all the way to B cup status, she led me into the kitchen and told me to sit at the table. After I took my chair, Lori went to the other side and before sitting down herself; she bent over the table pushing a bowl of fruit towards me. This allowed a full view of her chest right down to her belly. Ok, she had made it past the teacup size but was not yet up to cereal bowl size. What I did pick up on were the 1/3 visible rounds of her areola’s above her push up bra. My staring it did not get lost on her as she woke me up out of trance by saying:
“Hey idiot, those tits are jail bait now that you are 18 years-old”
I stammered, ”Ah…what?” as she sat down across from me.
Taking full advantage of my condition she continued, “too bad we did not hook up a few days ago, you might have had an opportunity to get a touch of my tits, maybe I would have even let you kiss them. Maybe I would have even allowed you to fuck me, maybe.”
By now my dick was harder than granite with the thoughts of what she just said swirling in my mind. Along with my mind’s eye painting a picture of Lori’s nude body spread out in front of me.
“Hey dickhead, get your mind out of the gutter” Lori shouted.
With that she pulled one of her tits out of the top of her dress, exposing an exceptionally large nipple and areola. She looked at me an said,” yep, too bad, you might have been able to have this” and then pushed it back in place.
She leaned on her elbow and said, “ from now on seems as though you will have to go after older women…or just old women.” She said with a laugh, “ maybe my Mom’s got some friends you could hook up with”.
Apparently from the expression on my face, Lori came back with. “What you think my Mom’s too old, not good looking enough?”
I relied, “ no, not at all, she is great looking for someone in their late 30’s”.
To which Lori responded, “ will you admit she is hot?”
“Absolutely”, I came back hoping Lori would drop it.
“Oh yeah, would you fuck her if you had the chance?” Lori shocked me again.
Not knowing what to say, I just shrugged my shoulders.
To which Lori responded, “ I can visualize your little dick trying to fuck Mom’s pussy, turns you on doesn’t?” She waited a second to let it sink in, then asked, “Answer me, you would, wouldn’t you? You are probably so horny right now that if you touched your dick it would explode thinking about my Mom.”
I blurted out, “yes, yes I would…your Mom is one hot 38ish woman, thank God she is married and looks at me as just kid.”
“40” Lori said. “ My Mom’s 40, now how do you feel?”
To be honest, at this point it did not matter, in fact it turned me on even more especially with the knowledge it would never happen.
“Well Jay, here is the scoop” Lori matter of fact stated, “ Russell left with my Dad this afternoon and will not be back till late Sunday or possibly early Monday. Fortunately, you might have a chance to get into my Mom’s pants because you are now elected to escort my Mom to a banquet tonight. Of course the fucking thing will just be a chance in a million with Mom, but if you take her, I promise that some day you will be able to put your little dick in this.”
With that Lori stood up and pulled the front of her dress up exposing her pussy to me, spreading the lightly haired lips allowing me to see the moist inner folds of her cunt.
You will take her, will you not?” Lori aked.
Again I stammered, “Yes, absolutely…when?”
“When can I fuck you?”
“We will discuss this after, remember that I am now jail bait”. She said. Then walked up to me and wiped her cunt juice covered finger across my lips.
Lori turned and yelled up the stairs, “ Mom, Jay will be glad to take you tonight. I’ll get him into Dad’s tux since they are about the same size.” She turned to me and said, “come on, have to get you ready quickly, my date will be here within an hour.”
Lori led me into the guest room, where a tuxedo was laid out on the bed.
She said, “hurry up, we do not have all day…strip. Do not be a sissy, you are going to need help, so strip.”
I quickly stripped down to my briefs, to which Lori laughed, “ you have got to be kidding, little boy underwear?”
She walked up to me and in one hard yank, ripped my shorts right off of me.
Looking at my dick, Lori said, “heck Jay, would never have realized it, but you have at least a normal size cock, I am surprised. Good size balls too, think you will have to go commando tonight just in case Mom gets a chance to cop a feel”.
I started to protest, but Lori grabbed my scrotum and said. “Quit being a baby”.
With that I completed dressing in the tux with Lori tying the bow tie, slapping some after-shave on me, and then handing me a Rolex to put on my wrist. Standing in front of the mirror, I do say that I was transformed in to a young good looking cosmopolitan stud.
Lori guided me out to the living room just in time for Mrs. Wagner to enter
She was stunning! Her black hair pulled tight into a ponytail on one side, yet framing a sophisticated gorgeous face with perfect makeup accentuated by bright red lipstick. Her black bare back satin dress had a deep V in front that opened to half way between her semi-exposed full breasts and her belly button where a thin rope of material acted as a belt with the long leads set off to one side. The dress culminated about mid-calf with a slit extending up the side of her right leg to just below her hip. Her four inch stiletto high heals accentuated her long shapely legs and when she moved the slit exposed just a hint of her lower right ass cheek. As she moved her breasts swung unencumbered yet firmly within the small confines of the loose silky fabric which must have been rubbing just ever so on her nipples as you could make them out through the cloth when her movements pulled the top of her dress to her body.
Mrs. Wagner walked right up to me, taking my hands and placing them on her hips, then placing her hands on my shoulders. Her smell was exquisite, almost closing my eyes as I breathed in the scent. It was as if I was in a different world, but I could feel every hair on my body standing up on their own as if being pulled from the outside by a magnetic force being emitted by her body, wanting to draw my whole body to hers.
Mrs. Wagner asked, “ Well Jay, what do you think? I hope that you will not be embarrassed by escorting and older woman like myself.”
I coughed, almost choking, “ Mrs. Wagn...”
She put a finger to my mouth and said, “From now on, please just call me Rachel, so what do you think?”
Trying to get our the right words I said, “Rachel, you are absolutely beautiful and am not only honored to be your date, I am totally at your service.”
She leaned towards me and said, “ let us hope you do not regret that”. And placed her luscious lips against mine, with her hand moving to the back of my head to pull me tighter. Our mouths slowly opened as I felt her tongue work it’s way into my mouth. I fully accepted her tongue alternately sucking it and then probing the inside of her mouth with mine. I slowly moved my right hand up her body from her hip stopping just below her left breast, it soft weight could be felt on the top of my hand. She never faltered, moving her right hand down the front of my body until she reached my belt.
Then Lori coughed loud, telling us, “Ok guys, break it up, you have all night.”
That broke our embrace, but as we separated Rachel allowed her hand to slightly brush my cock through the front of my pants. This stopped her momentarily, kind of an expression of surprise on her face, then a slight smirk as she turned away. I do not know if this was because she discovered that I was not wearing underwear or because my dick was hard enough to pound nails, never the less the front of my trouser stood out quite a bit.
Lori looked at my crotch then looked at my face and quietly said to me, “ you just might get the chance.”
The doorbell rang and Lori’s date arrived. I immediately recognized him as one of the detectives on the local sheriff department. He had to be at least 25 years old. Lori caught my expression and lifted her finger to her lips in a shushing motion.
It seemed strange that she tells me that she is jailbait to me, but going on a date with a cop.
Mrs. Wagner…err, I mean Rachel, and I arrived at the banquet, a very formal affair set up for some fundraiser pertaining to some Women’s organization. The place was filled with women ranging from early twenties to well over retirement age. It was quite evident that what men were there, had to have been dragged or bribed to go as they mostly congregated around the bar in the back of the ballroom.
Me on the other hand, well let me put it this way. Rachel strutted me around like she was showing off the crown jewels. She introduced me to young and old, good looking and some that would scare a locomotive backwards, as HER date. I could tell from her animated gestures that she was really getting into it. She then located a group of specific women and headed towards their location, whispering in my ear to play along with what she was going to tell them and she was going to make them jealous.
There were four women there, the youngest maybe thirty, the oldest no more than early forties. All had huge wedding rings on and all were dressed to kill, showing off each of their best assets. Rachel introduced me to each one, not only by my name, but also as her personal escort for the weekend. From the raised eyebrows amongst them, this definitely ignited their interest.
One of them, named Mary, who was about the same age as Rachel, leaned towards us and asked, “Rachel you aren’t…uhmm, doing him are you? He can’t be much over twenty one or so.”
Rachel just winked and then confirmed, “Need a young one once and awhile so they can keep up with me” as she squeezed my hand.
Jan, the oldest and apparent boldest of the group, looked both ways and stepped right in front of me grabbing my package hard through my pants. Squeezing my gonads and with a smirk said, “boy, I hope that Rachel is paying you big for these things” as she rolled both my testicles with force. It happened so fast that I did not have time to react and when I did, all I could do was turn red from embarrassment.
Rachel immediately responded, “ Jan, he is not that way, not even close, he is here on his own free will.”
Jan immediately let go, looked at me and apologized. Then said, “well boy, if you ever did need some compensation, feel free to find me. They definitely felt good to me!” She took a card out of her bodice and slid it into the waist of my trousers, then walked away.
The other three, Mary, Janet, and Sue all looked like they were drawing pictures in the sand with their toes. They must have had the wrong impression too.
Janet, a strikingly beautiful longhaired blond in her mid thirties, finally broke the uncomfortable silence and told Rachel, “I for one am jealous. Rachel, if I could or if I would have the nerve to walk in public with a young stud like this, I would be in seventh heaven”
Both Mary and Sue, a forty-ish thin and tall light skinned black woman, concurred thanking Rachel for introducing us and then joined the party.
To be honest, I was very much enjoying this, the implication of being a gigolo and stud status. Rachel cruised the floor while I strutted like a rooster at her side and as we sampled more and more of the champagne our motions became not only more fluid, but also the incidental contact became more personal and natural. More than once Rachel had placed her arm around my back taking care to slowly rub her hand across my ass cheeks and more than once she would lift my hand from her waist to the bottom of which ever tit was opposite the side of her I was on.
At dinner, with her sitting next to me, she had even placed her hand on my inner thigh then slowly slid her hand along my thigh until she had a handful of my balls, working them between her fingers and palm. She leaned towards me and biting her lower lip, she let out, “gawd, these feel good, damn I want them.” I knew then that I was going to win that one in million chance tonight…provided I did not blow it by doing something stupid.
After dinner we hit the dance floor, making sure that we managed to grope as much of each other as we could along with grinding our bodies together with the sway’s of the music. I had a perpetual hard on and my dick seemed as though it was trying to grow out of its skin. I had this animalistic feeling that I wanted to bend this woman backwards over a table and fuck her harder than any woman has been fucked in the history of man. Of course my fucking history was mostly written on my hand and had only managed to fuck one girl (my cousin of all things) twice, so you have to keep my urges in the proper context.
Then Jan broke in, kind of politely, but almost pushing Rachel away saying, “ok, let’s go big boy”. I thought she was going to crush me and with her being pretty short, my hard on was against her stomach with my cock head almost against her ample tits.
She noticed too, saying, “I can see you are happy to see me!” as she rubbed her body in an oscillating motion against my staining cock. She then reached between us with one hand, grasping the shaft of my cock through my dress trousers, looking up at me as she stroked up and down.
With my heightened sense of arousal from thinking about Rachel, and Jan’s superb handling of my cock, I thought that in moments it would be the most embarrassing minutes of my life.
But right before that happened, I was saved by Sue. She stepped in, pretty much pushing Jan aside and saying, “ don’t worry Jay, I’ll save you. Jan wanted to waste your load so Rachel wouldn’t get it, I’ll give you time to settle down”. We finished the dance with out any hanky-panky as my cock went back into stand by, but it was very obvious to me that my balls were really working overtime producing unused man gunk.
As I went back to the table, Sue whispered in my ear, “saved you tonight, but you owe me and I will fuck you silly” and with that she gave me a kiss on the cheek then moved off to join the festivities.
Rachel and I danced one last dance, and of course we both got aroused again with Rachel cupping my balls and telling me, “ we better get out of here before these explode!”
I do not think that I had even managed to get the car on the street before Rachel reached over and in a couple of moves had my pants open with my rock hard cock in her hand. She kneeled on the seat and told me to move the drivers seat all the way back as she then lowered her warm moist mouth around the head of my cock. My right hand moved across her exposed back sliding easily under the back of her dress. I could feel that she had thong underwear on as I lifted the string, moving my hand between the cheeks of her ass, with my fingers slowly probing to her anus, hesitating there for a minute then working my fingers to her cunt. She was absolutely soaked; her pussy was not only wet, but also radiating heat as if it was a furnace. The other sensation was the absence of pubic hair, as I could not feel any.
Slowly I moved my fingers into her gash, finding her tunnel to paradise and moving first one, then two, and then three fingers in and out. She started to co-ordinate her mouth moving up and down my cock with my fingers moving in and out of her pussy. Her mouth was working my cock in a way that made me want to scream and forcing me to hold back as I struggled to keep the car going in one direction. It was to no avail, as Rachel bucked hard against my hand, obviously having an orgasm, she bit down hard against the base of my shaft, the head of my cock well past the back of her throat. My balls contracted, forcing my cum into its journey through my penis and into Rachel’s throat. This was the first time I was the recipient of a blowjob and all my fantasies were not even close to that actual experience. My cock unleashed not one, not two, not three, but multiple ejaculations of my pent up seed. Rachel sucked in rhythm with each pulse until the last drop cascaded from the end of my dick.
She pushed up from my dick smiling at me with driblets of my cum rolling down to her chin from the corners of her mouth. She moved towards me planting her lips on mine pushing her cum covered tongue deep into my throat. Managing to get the car to the side of the road, I returned her embrace thinking only momentarily about that being my cum in her mouth. In fact I became more aggressive in my kiss, cleaning her entire mouth out with my tongue. We must have held our embrace for a good fifteen minutes until Rachel sat back in her seat, straightening out her dress.
I started to pull up my pants, but Rachel stopped me, reaching her hand over and taking my semi flaccid cock into her hand. She kind of played with it and said, “let’s keep this guy out until we get home” as she beautifully smiled at me.
The hour drive back to Rachel’s house after the first episode started by relaxing and enjoying the feeling of Rachel’s hand as she manipulated my cock, then my hand worked its way over to Rachel’s chest. She moved close enough to me that I was able free one of her tits. My God, it was a beautiful tit, perfectly formed with a ¼” hard nipple poised in the middle of silver dollar areola, the flesh of her tit soft, smooth, yet firm. Her tit barely sagged even though it was as big as half a large coconut.
Within a half hour, my cock was rock hard again and our movements gained more momentum. But Rachel held off just enough that I maintained my composure through the rest of the drive.
We barely managed to stop the car in the driveway as we both had the doors open and headed for the front door of the house. One of my shoes never made it out of the car, the other in the middle of the driveway, my pants almost stayed on until the front porch where I walked out of them, my cock swinging to and fro. Rachel never bothered to put her right tit back into her dress, like the goddess of Venus her tit proudly protruding for all to see in front of her. She lost both her high heals half way up the walk, her thong underwear crumpled up on the last step leading into the house. My coat somewhere thrown on the lawn, the last vestiges of my clothing ripped off at the threshold as Rachel pulled her dress over her head and then threw the dress off to her side turning towards me as crossed the threshold into her arms.
In the flash of a moment I saw Rachel in her full glory, beautiful face, firm large tits, flat stomach, a sliver of dark hair almost pointing to the top of her cunt.
We embraced hard, locking our mouths together, exploring each other’s mouths with our tongues as I lowered her back first to the floor right inside the open front door.
In what seemed like a seamless movement her legs opened and the head of my cock located the entrance of her wet, hot vaginal opening. It was impossible to stop the momentum, my cock head moving past her initial resistance, and then slowly plunging into the warmth of my goddesses cavern.
We never broke our embrace and our hips started co-coordinating with our thrusts, the feeling of my cock in the silky, wet warmness of her cunt, her vagina grasping my shaft in rhythm to my cocks in and out movement, her hard nipples pushed against my bare chest by her firm breasts. She reached around me pulling my body into her, her gorgeous legs wrapping around me. We thrust and thrust, our tempo ever increasing until at almost a planned synchronized second, Rachel pushed her head back moaned loudly as I felt a trembling through her body and uncoordinated bucking movements that drove my cock even further into her womb. Just then, my orgasm came with a bull rush and without control my hips drove my cock to the back of her womb, feeling as if the end of my dick had penetrated another room, pushing open a stuck door. My cock unleashed a powerful pulse of my seed filling that hidden room within the secret confines of my lover’s deepest channels. I came, and came again, each time Rachel meeting the pulse with one of her own.
Within a few minutes, we were both played out, lying together with my cock slowly withdrawing from Rachel’s pussy. We embraced again, for a few minutes as we rolled side by side. Then looked into each other’s eyes and if by a common command both of us said, “that was fantastic” at exactly the same time.
Rachel was the first to stand up, standing above me to close the front door; I had a view from the bottom to the top. She had a shaved pussy, now with her inner lips hyper extended and her vagina open from my cock having stretching it. There was a rivulet of liquid running down her inner thigh and a glob of my semen starting to drip from her opening. She looked down past her beautiful full tits, her nipples and areolas contracted and soft from her orgasm.
She smiled at me, asking if I liked what I saw. Of course I responded with “yes, I am looking at heaven.”
Reaching down she grabbed my hand saying, “ok stud, let’s go” as I stood up and followed her to her bedroom.