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.
Fah45 says
Not bad
Johm Smith says
Where is the finish story to Milestone. Ive read 1&2 but cant find the finish.
Johnny says
Great story
Bob says
In High School, at a friend’s house, his parents welcomed the four of us and his mother, a cougar about 35-40, great body and randy as was her husband, almost a meeting of minds & bodies happened but the husband seemed more interested in us so we got some cold water(summer) & left.
Lenard Maponda says
Good story That can make you cum.