This is a true story.

My 18th year was a quite a time in my life. More happened to me in the realm of sex than at that time in my life until I was about 49.
I had finally cum inside of a pussy for the first time when I was 18, that act came back to get me in ways I would have never ever thought. I ended up having sex with a daughter (I told that true story in “Surprise, then Complicity”) I never knew I had.
Are all things cyclical ?, I damn well hope not !.
I think one of my fondest memories of my 18th year was when I lived one of my dreams, which was to have sex with an older woman. I always had an attraction to older woman, not like I wasn’t attracted to girls my age or even near my age be it younger or older but when I was 18 I thought woman in their late 30’s and even in their 40’s looked so good.
Beautiful, mature, experienced and sexy, they were cougars before the term was even invented. I always had an affinity for brunettes and was very partial to Hispanic woman, but that is another story.
Beauty takes many forms and I have never denied opportunity based on age, hair, race or body type and such was the case I will describe below.

It was a summer night and getting kind of late at around 11pm and I was drag racing with a friend of mine. I had another friend in my car and the friend I was racing with had another person in his car, so 4 of us all together. There was a long straight section of road that ran past my neighborhood and we had made several passes down this section that ran between the road that entered my neighborhood and a convenient store about a mile past that.
On one of our passes my friends car malfunctioned and he coasted on to the convenient store parking lot. We got under the hood to determine the cause of his troubles and not being able to figure it out we decided to tow him back since we couldn’t get it to start again.
So me and the guy riding with me went back to my house to get my truck and bring the other car back.
We got back and as a last measure we tried to start his car again and after hooking up jumper cables the car started.

So the 4 of us were standing around just bullshitting when a woman in a white Buick Regal pulled in behind my truck and she appeared to just pull into the parking lot to turn around and she came very close to the back of my truck.
We stopped talking and nervously watched this woman steer her car as she came within mere inches of wrinkling her fender. She had her window down and as we watched she began to brag about her driving prowess while she finished making her turn and stopped where we were standing.
She had short blond hair, blue eyes, looked to be in her early 40’s, she was pretty and appeared to be drunk, actually he seemed to be tipsy rather than DRUNK.
I don’t remember exactly what she said that caught our attention but it was apparent that she was hinting for some company. I think she asked if one of us wanted to ride with her or approve of her driving or something to that affect but anyway there appeared to be opportunity so the 4 of us looked at each other, not quite sure what to make of it then we all declined.
She said something that was unintelligible then slowly drove off then after a minute my one friend and I decided to follow her.
We jumped in my truck and headed up the road and just as I was passing my neighborhood we came up behind her, we were a little interested because we weren’t sure exactly how drunk she was so we worried about her having an accident and of course out of sheer curiosity I wanted to see if there was potential.
I followed her to a major intersection and while we were stopped at the light I beeped my horn at her when it turned green, she stuck her arm out the window to wave then made the turn and pulled off the road so I pulled up behind her.
I got out and walked up to her door and asked if she was alright. I watched her drive for at least a mile before we came to this intersection and she didn’t weave or drive erratically rather she drove cautiously, this was obviously wasn’t her first time at doing this.

She asked me to get in her car and she would take me home with her. I was intrigued and nervous because here I am faced with an opportunity I always wanted but this just seemed to damn easy, there had to be a catch and that is what made me nervous.
I looked at my friend, who was still sitting in my truck, and she chided me for looking over at him when she asked me to go home with her.
I wanted to get mad about that but I was being cautious plus I was struggling between my two heads, I didn’t want the little head doing the thinking for the big head, so I weighed things out.
I told her she had been drinking and I was worried about riding with her and she said I could drive, she proceeded to move over the console and get in the passenger seat.
I hollered to my friend to take my truck home and that I would see him tomorrow. He had a wide eyed look on his face and as he scooted over to the drivers side he leaned out the window and asked if I was sure, I affirmed by nodding my head.
I got in her car and she guided me to her apartment which was on the other side of town form where I lived. I don’t remember the exact conversation while we drove to her place other than a few things like where I worked and where she worked.
She was a nurse at a large hospital in town and that was another fact that just set me on fire. I had worked at a hospital down in Texas just prior to this and was surrounded by nurses. The one thing that was evident then was that nurses could be divided in two categories, hot and ugly, there seemed to be no in between.
I used to just lust after nurses all day long when I worked in that hospital in Texas, it was torture for a young man and I always wanted a nurse and now I was going to have an older woman who is a nurse !. I thought Christmas had come early.

We got to her apartment complex and walked upstairs to her place, not knowing what to expect I nervously entered and was surveying the living room while she escorted me right to the bedroom.
She got to the bed and pulled the covers back then said she would be right back.
I heard her in the bathroom making noise and running water. Things were going fine so I stripped my clothes, except for my underwear and sat on the bed and waited.
She came back in with a thin nightie on and I stood up as she came to the bed. She was shorter than I, me being 5’8″ she was about 5’6″ and like I said before she was in her 40’s and weighed maybe 130lbs. She was firm yet squishy in the right places and she appeared to take good care of herself.
We wrapped arms and kissed, she brushed her teeth but the smell of alcohol was still there and while she had a pretty good buzz she never staggered or swayed and she had all her senses.
I had been with a few girls and I was ready to get busy so while we kissed I reached down and went straight for her pussy,
“Go slow lover, take it easy”, she said.
I admit I was probably somewhat clumsy and hurried but at 18 I just wanted to bang one out but she wanted us to take our time. Hell I knew I was good for several sessions through out the night, I was sure she was counting on that, so I didn’t see a problem with getting off a quick one but she had other ideas.
“Come on, lets lay down”, she said.
We got into bed and started to hold each other and kiss, my hand automatically drifted down to her pussy but I didn’t dive right in rather I brushed my fingers over the top of her panties instead of sliding one into her slit again. I would back off of that and run a hand down her leg and over her hip and then squeeze.
Damn she felt good, she was more than old enough to be my mother and I relished the experience with this woman. Sure teenage girls were just as hurried as I was and after a little foreplay we would be eager to get busy but this was different.

I struggled to keep myself from applying my instinctive and youthful exuberance but I knew I would be more calm and slow if I could just get a load off first.
This was so hot, I was going to get some strange, I never did know her name nor did either of us inquire, she was older and kind of drunk, we picked each other up late at night by happenstance…………..I used to read and hear stories about this but never lived it, until now.
After some kissing, hugging and rubbing time I attempted to get things going where I wanted to so again I played with her pussy and finally she was more receptive as I got under her panties and began to slid them down her legs.
Once that was accomplished I continued to kiss her while I gently slid my underwear off.
Things were finally getting heated and I kissed her neck while I worked a hand up her flat and incredibly toned stomach with my destination being her titties which were a good handful and in proportion to her body size.
I was finally getting her hot now and she pulled away from me and took off her nightie and we were both finally and totally naked.
She noticed I was getting hot and by hot I mean temperature wise. She pulled the covers down off of us and she began blowing on me to cool me down, she paid particular attention to my groin area and she was getting closer as she scooted down the bed. She kept playing with my cock and I laid there with my eyes closed while she literally blew air across my lower body.
I was slightly on my side due to our previous position from hugging and kissing and finally finally she put her mouth on my cock and I melted.
I couldn’t make a noise, no “OHHH, or AHHH, or UHHH”, I just laid still, almost in shock and disbelief that this whole thing was happening while she worked me slow and easy, I breathed evenly and quietly while she worked up and down. She was a small woman and her mouth wasn’t that wide so she had trouble.
I looked down and her mouth was stretched to the limit with just my cock head, she did keep her teeth out of the way while she tried to take more.
I put my hand on the back of her head and wanted to just fuck her mouth, I pulled her head slightly and thrust my hips forward some and she was responsive, she tried to swallow more of my cock while I attempted to force her but it was more than she could handle.
This is nothing I haven’t experienced with other girls because I do have a rather thick and wide cock.
She liked me trying to force her onto my cock but when I did get more in she couldn’t keep her teeth out of the way enough to take my girth so she bobbed on my head and after a couple more minutes she was done and pulled off.
She was breathing very hard, you would think she held her breath the last 5 minutes but after several gulps of air,
Damn, you are a big boy, aren’t you”, she said while she continued to breath.
“So I’ve been told”, I responded.
“Take it from me sweetie, you are”, she said.

Nothing like stroking a teenagers ego that’s for sure, I never really expected her to suck my dick, the only thing I had on my mind was her pussy but I’m not complaining.
While she scooted back up and put her head on the pillow and laid back to breath I worked my way down after quickly sucking her titties and arrived at her neat little snatch. She didn’t shave but she obviously kept it trimmed, there was just a tuft of light blond hairs covering her mound.
As I got myself into position she opened her legs and bent her knee’s just slightly while I licked her for the first time. I wasn’t sure what to expect with a woman so much older, way older than any pussy I had to date.
What I found was that pussy is pussy but hers didn’t really have much smell to it and the taste was pleasant as well. I was in my element now, I licked her pussy and with a hand on the top of her cunt I used my thumb to rub her clit.
She opened her legs more and raised them and while I worked she flexed her hips slightly and moved with me while I ate her cunt.
With her experience I was worried I didn’t know enough to please her but when she began to pant I knew I was doing just fine, she was turning me on more and more with her panting and flexing, my cock had been hard for quite some time now and I needed to be inside this woman.
I stopped licking her and began to move up but she pushed my head down and wanted more, I had licked her for at least 10 minutes and the underside of my tongue was sore from extending it and I needed to rest plus I wanted to get inside of her.
Not wanting to disappoint I went back down and tongued her just a little more then attempted to move up, she pushed me down again but I had enough so I moved up while she continued to push me while I mounted her.
She actually struggled with me and while she couldn’t close her legs with me between them she lowered them down a little while I reached down to position my cock.
She was pushing at my hips while I pushed into her all the while she struggled and grunted as I entered her. With my cock inside and no longer in need of my hand for guidance I leaned over her some more and was attempting to plant my hands on the bed on each side of her to support myself. She grabbed my wrists and pushed and I twisted my hands and grabbed her wrists and pinned them down and started to move in and out of her while she grunted,
“UH, UH, UH, YOU BASTARD, YOU THINK YOU’RE GONNA FUCK ME”, she said.

It was at this point I was thinking “this chick is kind of weird” and I wasn’t sure if she just wanted to lead and have all control over every aspect of this whole thing between us tonight or what.
I was actually getting worried but one thing for sure is that if she would have said STOP or NO then that would have been it for me. I would have quit.
I held her wrists and as I pumped into her I widened out my legs to force her legs open a little more and with that done I sank more cock into her. She was actually tighter than any “girl” I had (with the exception of a 15 year old I had when I was 17) and her cunt was very soft inside.
I felt it was more and even better than I expected and dreamed about when I used to jack off to the thought of fucking on older woman, with the exception of the struggle and I was worried about myself because I knew my lust was getting the best of me and I didn’t want to stop until I shot off.
“ASSHOLE”, she sneered at me. It was feeling so good but this was something I didn’t expect and if I had to struggle like this until I shot my wad then well……..I wasn’t going to shoot off like this.

I quit pumping and looked down at her,
“DO YOU WANT TO STOP” ?, I frustratingly asked as I loosened the grip on her wrists. I was serious but inside I prayed she didn’t want to stop because she felt so damn good and I needed to shoot off really bad, preferably inside of her and not in my hand later.
“ARE YOU A BOY OR A MAN”, she said in a sarcastic tone.
That kind of pissed me off but my lust was making the decisions and without a, “I want you to stop” or any other indication from her that she wanted to quit, I didn’t pull out while I assessed the situation.
With her hands loose she reached up with both hands then grabbed and pulled my hair,
“YOU AREN’T A MAN”, she she said through gritted teeth as she strained while pulling my hair.
“OOOWWWW BITCH”, I said.
She was damn well hurting me now and I thought perhaps she wasn’t drunk or buzzed as much as she was mental. I reached up with one hand, while still supporting myself with the other and pried her hand loose then pinned it back down to the bed, she flexed her wrist and scratched the back of my hand with her fingernails.
I reached up with the other hand and got her to let my hair loose and I again had both of her wrists pinned down.
“YOU FUCKER, YOU GONNA FUCK ME, BOY !, HUH ?”, she said.
She was mocking me now but I was pretty much convinced as to what she wanted. At 18 I was totally inexperienced in this stuff but the whole scenario from her initial approach, to the pick up, to the point right now in her bed, was designed for one thing.

I was somewhat pissed, confused, a little worried and very horny. I started to to pump into her again while keeping her wrists pinned tight and she was still flexing and scratching me hands with her nails. I slid my hands a little farther down her arms and was still able to keep control and be out of reach of her nails.
I pumped faster and faster while she continued to grunt and gasp but her struggling seemed to ease after a little bit, her head went to the side and she closed her eyes yet kept a twisted look on her face and gritted her teeth.
I didn’t ease my grip on her arms though and I wasn’t going to take the chance because not only did she extract some hair from my head I think she scratched my scalp with her nails, nails hell she had talons.
It was a good thing I didn’t let my grip loose because she suddenly began to flex and claw me again so I applied more pressure and she tried to move her whole body and let her legs down so I widened mine a little more to keep her legs open and I started pounding her cunt even harder while she struggled,
“YOU INTENDED TO RAPE ME, YOU BASTARD”, she sneered.
Now in latter years I became more accustomed to this language and such a scenario but at this age, and my limited experience, just the word “rape” struck terror in me.
I was worried but close to cumming as well and I only wanted to finish, I had to cum and within my head (the little one and not the big one) I felt I could justify things because, well, because I just had to cum.
“NO”, I said in a worried tone. I was worried, worried like hell that this thing could go bad and if she started screaming then at what point constitutes rape ?
I could get right up to the point of getting my nut off and then she says lets stop or starts screaming…………… god this was crazy I thought while all kinds of scenarios ran through my mind.

I was still pumping away and didn’t let up a bit but she did give up just a little bit yet again. I was breathing hard because even at 18 the pounding I was giving her cunt plus the constant struggle and tightness of all my muscles had taxed my oxygen supply.
I did get a sign of encouragement though and it helped ease my mind and bring me to a finish.
“RAPE ME, RAPE ME YOU BASTARD, RAPE MEEEEEE”, she moaned.
I reached deep down and ignoring the burning muscles I summoned the extra burst of energy I needed for both of us as I hammered into her harder and harder and gripped her arms tighter.
While I fucked her I looked down and her face was no longer twisted but her mouth was open and she panted, I couldn’t hold my load and longer,
“UHHH, UHHHH, UHHHH, I HAVE TO DO IT”, I said in a much labored tone,
“UH HUH, IT’S OK LOVER, IT’S OKAYYYYYYY”, she responded blissfully while pulling her legs up higher.
After a few more strokes I shoved as deep into her as I could,
“OH MY GOD, OHHHHHHHH”, I yelled out as I blasted a long satisfying stream of young gooey spunk deep into her soft pussy. It was such sweet relief shooting off into this stranger, this older woman, one I finally had sex with. It was the culmination of one of my dreams, so good that I had a little more in me,
“UHHHHHHH BABY”, I groaned out as I shot another spurt. I held inside of her as my body tensed then released over and over while my cock convulsed to expel any trace of cum into her.
I couldn’t pull out, I left my cock deep inside as I jittered and shook. It was intense, I mean the entire series of events was so intense that it just blew my young freaking mind.
I finally pulled out and laid on my back while my whole body continued to tremble, the feeling was one of well, the only thing that was even close was when I shot off inside a pussy for the first time (which also happened when I was 18) but this was even better than that as far as intensity and hotness.
She laid on her back breathing erratically while she quietly stuttered,
“oh my god, oh my god, ohhhhh”.

I didn’t know what to make of it and I alternated between worry and satisfaction. I was laying there convincing myself that she craved this whole scenario and wouldn’t be overcome with regret after enticing me to fuck her, forcefully fuck her, well a mocking forceful fuck anyway.
We both laid there for several minutes as our breathing evened out and we returned to a much more calm state and it got quiet. I needed confirmation everything was alright here but was almost afraid to move, talk or touch her. Like I said I still had thoughts this whole thing could turn bad, I feared a touch may send her screaming or something.
I was young and inexperienced but I needed to do “something”, so I rolled on my side and put a hand over her stomach and she responded by placing her hand on mine.
“Are you OK”, I asked.
“Whew, that was incredible”, she said. I was relieved inside but this whole thing took more out of me than I expected. I can usually go again and again and could fuck and cum several times in the span of 2 or 3 hours but I was done tonight. While I was spent, sexually speaking, I was awake and full of energy.
I had no intention of staying the night with her initially rather I intended to get some pussy and be done with it. Again being young and exuberant I never took the time to be affectionate and loving and all that, these things didn’t come to me until my later years.
She didn’t cuddle up to me or seem to want me to cuddle up to her. She rolled on her side away from me and pulled the covers over us and she appeared to be content for the night.
After maybe 30 more minutes like this and nowhere near sleep, I got up and began to put my clothes on.
“You don’t have to go”, she said.
“That’s alright but I should get back home”, I said.

She got a little agitated and then got outright mad,
“Get the fuck out of here and make your own way home, I don’t owe you a damn thing”.
“FINE, can I at least use the phone”, I asked.
“YEAH use it and get the fuck out”, she said.

It was to late to call my friend at his house and wake up his parents, there were no such things as cell phones back then so I called a cab.
She still tried to get me to stay but I wasn’t interested and knew I would have some explaining to do when I ever got home so I left her place and went outside to wait for the cab.
After I was home it hit me that I left my hat in her car, I figured I wouldn’t see it again.
I didn’t have any explaining to do, my mother knew what happened. My friend drove my truck back to my house instead of to his own house and when he dropped it off he told my mom I went off with a woman I didn’t even know.

I saw my friend every day of the week and about a5 days later he came by and had my hat in his hand. He said he ran into that woman at a store and she remembered he was with me that night and to give me my hat back.

It was a crazy time and one I will never forget. I never had any other strange after that, it was always with someone I knew or got to know but it will be an experience I will never forget.