After Michelle, I had moved on to Stefanie.
Stefanie was another friend of a friend, lived nearby but in a different school district. We had belonged to the same country club, which we both quit when we got separated, but we didn’t know each other well. A mutual friend had gotten us together a few years prior, soon after I separated, and we had one “date”, a quick drink. At that time, Stefanie thought it was too early for me to be dating, and suggested maybe we get together some other time.
So now about a year and half later, I reached out again, and she was game for another first date.
Stefanie was 46 (I was 49 by now) about average height. Dirty blond hair, kind of mid-length Karen-style, pretty attractive, maybe an 8 out of 10. Stefanie was very athletic, almost too much so. She ran constantly, played soccer and tennis, and was very, very active. Her friends all described her as “intense.” As a result, her smallish but round ass was hard as stone. You could bounce a quarter off her fine ass. But, her tits were almost non-existent. Heck mine were bigger. She had one child, a teenager child born through a cesarean.
Our second date was the same as the first over a year earlier – beers at a local sports bar. Although she was obviously concerned about her body, due to her constant activity she was able to eat just about whatever she wanted. She didn’t limit herself to salads and water. She ate burgers, drank beer, etc. So we ate and drank and had a good time, and ended the evening with a quick hug in the parking lot.
A week or so later, we had dinner, then went back to her house for a nightcap on the deck. I was expecting the usual pattern to emerge – second date (in this case really the third) establish that the man isn’t likely to be a serial killer, and jump into bed. Instead we hung out for another hour, and we called it a night. At her door we hugged and kissed, with some tongue action for the first time. She was taking it slow, which was fine.
A few nights later we were out again, and she mentioned that her sister might stop by, which she did. We drank beers and did a couple shots with her and had a great time, and when her sister left, we went back to Stefanie’s house.
She asked, “Do you play pool?”
I said, “Yeah, and I’m pretty good.”
We went into her beautifully finished basement, with a big TV and sectional sofa, pool table, ping pong table, dart board, and pinball machines. All kinds of games. We played two games of pool (both won by me) and then moved to ping pong.
Talk about super competitive. We split the first two games. I had grown up with a ping pong table and of course played a lot of pool and ping pong in my college days, so I was no pushover, and I sure as hell wasn’t going to let anyone win.
The third game was back and forth, and whenever I would score a point, she would mutter, “Fuck me runnin’.”
One time I laughed at this, and she said “Haven’t you ever heard that before?”
I said, “No, not said like that.”
And she said, “It’s funny because, try to picture fucking someone who is running.”
I said, “Oh I’m picturing that right now, but she’s playing ping pong.”
She laughed and took that comment very well.
I won the third game in extra time, and we were actually sweaty from the workout. I think she actually needed me to win. It was a test. Maybe she couldn’t get with a guy who couldn’t beat her, kind of like a male dominance thing. Who knows. But I think that the games and the sister were both tests.
We grabbed our drinks and I moved in to kiss her. She responded urgently, and we were Elvankent Escort well past the gentle goodnight kiss stage. Things were escalating quickly with our mouths and hands. If we had been at my house, I would have suggested that we take it upstairs, but since we were on her home turf, I figured it best to let her lead.
Before long, she did.
“Let’s go to my bed,” she said.
I said, “Lead the way.”
We jumped in her bed and picked up where we left off. It was a warm spring day so we had dressed lightly, her in a mini dress and me in just shorts and a golf shirt. I reached under her dress to find a bare, freshly shaven, and wet pussy. One finger in and I felt how tight she was, tighter than Michelle.
She said, “Get your shorts off and fuck me.”
I ripped them off and shoved my cock in her in about two seconds. My shirt still on, her dress still on. No foreplay, just raw fucking. Geez she must have been building up for a while and once she decided it was time to fuck, there was no stopping her.
Like I said, she was tight, definitely tighter than Michelle. The cesarean birth and all the exercise kept her tight as a virgin.
To my shame and horror, I came embarrassingly early. I was mortified. It snuck up on me and I couldn’t stop it. She didn’t even get off! It was the worst feeling you can have sexually as a man.
To her credit, she reacted like it was the best sex of her life.
She said, “I can feel you coming in me” and some other grunts and moans, but I was sure she was thinking “what a two-pump chump!”
I rolled off of her and apologized profusely, trying to explain that I was so turned on and it had been a while and yada yada yada. She seemed legitimately fine, and by the time I left, I was almost convinced that it was not a big deal. Still it weighed on my mind and I was determined to do better next time, if there was a next time.
Next time was about four or five days later. We stayed in touch through text, and she said that her daughter would be away on Friday night with a friend, so could we get together “for the whole night?” My kids were with my ex, so I said that this would work great for me.
Now, about a year or so before this, I had gone to see a urologist for my first prostate exam. We talked sex, and I told him that I wasn’t having any ED problems or anything. He said that was great, but he gave me a sample pack of ED medicine in case I ever needed it in a pinch. I considered this a pinch – I wanted to be able to fuck Stefanie several times and I didn’t want to have any barriers to that. So I popped one and we met at her house to throw some burgers on the grill.
We ate on her back deck, which was secluded, overlooking some trees which dropped off to a creek down below. Very private. As we sat around the table chatting after dinner, I could see up her tennis skirt that she wasn’t wearing underwear again.
I said, “I like that easy access skirt.”
She grinned at me.
I said, “Pull it up a bit.”
She did, she inched it up her thighs until I could clearly see her cunt.
Then I said, “What did you have in mind for dessert?”
She got my drift and spread her legs. I dropped to my knees on the deck and spread her legs wider with my hands. Stephanie slung her legs over the arms of her deck chair to allow me maximum access, and I went in on a mission. Her pussy was so damn sweet, it’s like she coated it with sugar after she showered. I don’t mean the smell of a stripper that uses perfume, I mean the smell and taste of her fluids Beşevler Escort was like candy.
I lapped at her like a kid in a literal candy store. As I’ve said, I love to eat pussy and I’m pretty good at it, and she got the full treatment. I got her off three times before she cried no mas.
She grabbed my hair and pulled my mouth off of her, and said, “Time to switch.”
I sat back in my chair and took my shorts down while she ran to a storage trunk to grab a seat cushion for her to kneel on. By the time she got back, all of about five seconds, I was stroking my cock which, thanks to the little blue pill, looked bigger and harder I think than it has ever been. I could actually see the blood pumping through the blue vein on the side of my cock.
She said, “Oh, there’s my big boy” and knelt to start sucking me.
She started with most of her focus just on the head, which was so big that it looked like a purple golf ball. I was hoping I didn’t burst immediately again. She licked and kissed the head, just under the rim on the front, running the top and bottom of her tongue all over it. I was oozing pre cum, which she greedily lapped up. Then she pursed her lips in a kiss and ran her lips up the front of my shaft, at least a dozen times, before lowering herself to my balls.
Her tongue snaked out and lapped at my balls, then she took them into her mouth and coated them with her saliva. Then, for the first time in my life, she lowered her mouth and let her tongue explore my asshole. I jumped a bit, which she may have been expecting, because she had a hand on my stomach which she opened flat and kind of steadied me.
It was such a dirty feeling. I can’t say that it was overly pleasurable, certainly not compared to a blowjob or sex, but the naughtiness of it, and knowing that she did it without me even asking, is what made it so great. She ate my ass just for a few seconds, then made her way back to my cock, which by now was a loaded weapon.
She licked the head some more while looking at me, then said, “I want your cum.”
I simply nodded and she swallowed my cock, not all the way, but far enough, and worked me with her mouth and hands. It didn’t take much more, and I was pumping a record load into her mouth. A couple drops dripped out the sides of her mouth onto her hands.
When I was done, she licked up the escaped cum droplets. She sat back on her knees and said, “What a great dessert. Did you like that?”
I said, “I loved it. Everything. Thank you.”
She smiled, took a swig of her drink, and we started clearing the table.
After we cleaned up from dinner, we returned to the basement to throw some darts (she won) and later put on a baseball game to watch from the sofa. Before long of course, our tongues were dancing and our hands were roaming. She worked my shorts off, and sat on me. I hiked up her skirt and slid my cock into her as I had the week before.
She sat there still, and we removed each other’s tops. Her tits were just so small, it’s like they were just nipples. She apologized for her small bust, and I assured her it was not even an issue (what else am I going to say?). She humped me sitting on the couch through two orgasms, and I felt like I had redeemed myself from my previous premature embarrassment.
I rolled her over on the couch, so that she was sitting with her back against the back. I got between her legs and put my cock in her, then got up on the balls of my feet, raised her legs onto my shoulders and leaned forward, literally folding her in half. Her feet were Cebeci Escort simultaneously next to my ears and her own ears, if you can picture that. She was so flexible from all the exercise that it was no problem for her at all.
Her toenails were painted a bright red, and she wiggled her toes against my earlobes while I was fucking her. She was still ridiculously tight, especially in this position, but given my earlier orgasm in her mouth, I was able to hold out for a while.
Finally she said, “Jesus you’re big, I can feel you in my stomach. It feels so great. When you come, really force your cock all the way as far as you can.”
With a final few strokes, I leaned all my weight onto her and forced my cock into her as deep as I could, and shot a big load into her tight pussy. She gripped me with her pussy and held on for dear life while I finished orgasming.
When I tried to pull out, her grip was still tight, and she smiled at me and said, “You’re not going anywhere.” I literally had to pull myself out of her.
We went up to her bedroom after that, and fell asleep watching the end of the ballgame we had started.
The next morning around six o’clock, I felt Stefanie’s hand on my cock, then her mouth.
When I was hard she rode me until we both came, then she whispered in my ear, “Go back to sleep, I’m going for a run.”
I hopped in the shower while she was gone, and was in the kitchen in a pair of gym shorts and a T-shirt, drinking coffee when she returned.
She said, “I’m going to shower, make me a cup please?”
She came down in a short summer robe as it was a very warm spring morning, and we went back to the deck to sip our coffee. We were standing along the railing of the deck, looking into the woods. A few deer came out and watched us watch them. I could see just the bottom of Stefanie’s ass cheeks as she leaned forward to get a good look at them.
I reached over to rub her ass, and she slowly arched her back to stick her ass out more the longer I rubbed.
I said, “Don’t move” and I knelt down behind her. Spreading her ass cheeks, I shoved my middle finger into her wet cunt while I tongued her asshole. After a few minutes, I replaced my tongue with my index finger, and before long I had a finger in each hole, making a “V” with my fingers while I stroked in and out.
I went deeper and deeper, without protest, all the way to the hilt, and it became apparent that Stefanie loved her some serious anal play. I filed that information away, and eventually stood up and shoved my cock into her pussy from behind. I pulled off her robe- she was now completely naked on her deck getting fucked from behind. No one could see unless they were walking through the woods on a Sunday morning walk, which was possible I guess, but if she didn’t care then I didn’t either.
I pulled her shortish hair into a make shift ponytail, and gave it a tug, which she seemed to really enjoy, so I took it a step further and grabbed her hair from the scalp on top of her head with my whole fist and yanked her head back. This is usually better with a mirror, but out in the open, it was so animalistic. I channeled my inner beast, and humped her into oblivion. I felt my cum boiling, and without warning I pulled out, spun her around and pushed her onto her knees, and came in her mouth and on her face.
Stefanie and I dated for about three months. The sex was good, and I was right about her being into anal. I fucked her ass regularly starting the very next time we were together. For such a small tight ass, she had no problem taking my cock all the way.
But, her daughter lived with her full time, so it was tough to get together regularly. And if I wanted to stay overnight then her daughter was sent to her dad’s, which I guess was a bad situation, and that kind of made me feel bad. So we ended things amicably. We did have a couple quick booty calls over the summer, but she met someone else shortly after.