Sam, How I Surprised Her

I met Sam at the mall. I was walking to foot locker and decided to have a coffee. As I was sitting down, I noticed a woman, must have been early 50's, walking towards me. She asked if she could sit with me since every other chair was taken. I said sure and we introduced ourselves. She was about 5'6", maybe 140 or 150, nice shape, brown hair and green eyes. She had a gorgeous smile and smelled amazing. I am a 5'10", 240 muscular pound man, 25 yrs old. I am Italian, with short dark hair, bright green eyes, and a neatly trimmed moustache and goatee. I have one tattoo, my family coat of arms, on my right shoulder. I am by no means a lifeguard type of guy, nor am I an obese roly poly guy. Picture a football player or heavyweight boxer, or even a bouncer. Big, muscular, but with a gut, just not a huge one. A 38" waist. Downstairs, I have been blessed with a decent length cock, about 7.5 inches, but I am extremely thick and wide, definitely allowing me to fully expand a woman and feel her lips surround me.

We continued to talk and sipped on our coffee and I had to go. I took a chance and asked if she was married. She said no and asked if I was hitting on her. I felt myself blush and admitted I was. She handed me her card and said to call her if I wanted to take her out sometime. I smiled and went shopping for the clothes I needed.

That night, I was watching the Monday night Football game and couldn't concentrate on the score. I kept thinking about the woman I had met earlier. She obviously worked out, so I started to think about a way to take her out. I figured that with her age she must be taken out by guys who always take her to a dinner, a movie, show, etc. and I decided I would be different.

I called Sam the next day, throwing all caution to the wind and not caring about those games people play. Like waiting three days, etc. She answered and I asked her to meet me at a park near downtown with some active wear and a change of clothes. She giggled like a schoolgirl and said she would come prepared.

Saturday came and at 1:00 I was playing basketball in the park. Sam showed up looking amazing. She has on a sports bra that accentuated her large breasts, revealing deep cleavage and showing a mostly flat tummy underneath. She also had on a pair of shorts that stopped just above where her ass stopped so she had two little ass cheeks hanging out. "Perfect," I thought to myself, "Now I have to try and control my dick from getting hard while I watch her."

"Hi Jason, I hope I'm not too underdressed, but it's hot and I didn't know what we were going to be doing."

"Sam, you look amazing. I definitely approve, and we are just going to play some basketball to get our ya-yas out and have some fun before dining tonight."

I gave her a big hug and felt her breasts mash against my shirtless chest. I kissed her on the cheek and gave her the ball. "First one to 21" I said and let her dribble around for a little bit to get warmed up.

As we played, I noticed how firm her body was. For a woman in her 50's, she obviously worked out. She had a little jiggle in her ass and midsection, but other than that, her body was taut and firm throughout. I loved when she would back me down in the pain and my cock would be pressed into the flesh of her ass. I wasn't fully hard or soft, so I am sure she felt me as she continued to do this through out the game. We were laughing and having a good time and it was 20-19 me.

"Jason, wanna make this interesting?"

" How so? I don't want to bet money or anything. So what do you propose?"

Sam thought for a minute and then said that whoever wins gets to cum first when we have sex later. My jaw dropped and my cock was instantly hard. "Looks like that's a YES" she said pointing to the tent in my shorts. "Don't worry Jason, I've been planning on seducing you since I saw you at the mall."

Well, needless to say, she had the ball, she dribbled left, and then backed down into me, grinding her ass into my cock. I decided that since she was being so forward, I reached around and let a finger slide up the back of her thighs, into her shorts and poke right into her already dripping pussy. She jumped straight up, and I grabbed the ball and shot it in to win the game.

"Looks like someone knows what he wants too. That's good because I already know I'm going to love feeling you in me." Man, she was turning me on more and more with ever sentence.

We were supposed to go to dinner that night, but I couldn't wait any longer. "Sam, why don't we go back to my place and I collect my winnings? I don't think I want to wait to experience you."

"Why don't I just give you a blowjob in your car since the prize was just to cum first? Then we can continue. I mean, you aren't trying to rush me into anything are you?"

When we got into my car, she kissed my ears, my neck, my mouth, telling me she wanted to taste my whole being. She reached into my shorts and her cold fingers slipped in to caress my hot cock. She pulled my cock out and immediately lowered her mouth to take me in. Her mouth was hot, and I felt like my cock was in an oven. I let my right hand slip into the back of her shorts and cup the ass that had been teasing me all day. It was smooth and I was enjoying every minute of this wonderful woman working on my fleshy meat, her mouth opening wide and her lips touching the base of my cock and then tightening, sliding back up my shaft before meeting each other after flipping off my mushroom helmet. I got a little daring and pushed my index finger into her puckered brown eye. I know it was dry, so I just massaged her anus in a circular, pressurized movement. She moaned in approval so I continued to do that while she bobbed on my cock. Just as my finger did manage to break through and inch slowly into her ass, my cock started to stiffen and She deep throated me awaiting my semen. I didn't disappoint. My cock started spurting torrents of cum down her throat and she didn't move, swallowing ever last drop and then sucking hard, like a lollipop to drain me of my last fluids.

We kissed, and I started to drive back to my place to take turns showering and get ready for dinner. I tried to sneak into the bathroom while she was showering, but she had locked the door. No biggie I thought, and found out she just wanted to make sure she was beautiful for me after dinner.

We drove to the restaurant and I had another surprise. The waiter met me at my car with a basket full of cheeses, a bottle of wine, and a platter of wonderful Italian food. I paid and we drove to the beach.

After setting out a blanket, we fed each other the cheeses, sipped our wine and would kiss every now and then between laughs and talks. She was wearing a dress with her breasts, which were braless, hanging by two very thin pieces of cloth that continued up to attach at her neck. I cleaned up the food and I sat with my legs parted and outstretched, inviting her to sit in front of me. We watched the sunset and my lips explored her neck, earlobes, and back as I found her scent intoxicating.

I was feeling my cock grow behind her and she would nuzzle against it as I continued to kiss and nibble on her neck and shoulders. I reached around and let my hand enter one of the pieces of cloth pressed against her breast and felt her nipple stiffen between my fingers. She was moaning excitedly and I continued to be patient and arouse her very, very, slowly.

I then asked her if she had a good day and she just smiled and said it was wonderful but she was cold and loved near here so we drove to her place.

" Jason, you have been patient all day, and I know how much you have wanted me, but I need you to go lie on my bed naked and waiting for me. I promise you won't be disappointed."

I lay on her bed, nude, watching the ceiling fan above me spin, listening to her bustle around I the other room. She had a quaint room, some jewelry and perfumes on the dresser, soft sheets in a USC Trojan-like cardinal and Gold. A woman after my own heart.

Sam walked in with a pair of stocking on and her breasts, which I have since found out are a 44d were jutting out, with a little sag, but definitely still full and voluptuous. Her neatly trimmed pussy was evident to see with a little landing strip of hair leading down into her awaiting flesh. Her Hair was still up, and it showed her neck, which was very elegant looking. She walked over to the bed, laid down beside me and didn't move. I knew it was my turn.

I moved beside her, looking her up and down three times, soaking all of her body up in my gaze. I then took a hand and grazed her skin, her thighs, her stomach, the middle of her breasts, and then down again, her cheek, an arm, her thigh. She was trembling in anticipation, her musky scent beginning to fill the room. I leaned in to kiss her neck and she shuddered as my hot breath blew against her now goose pimpled skin. Her nipples stiffened and I kissed each breast, first the underside, then the top, and finally taking a nipple in my mouth and rolling it over my tongue. Sh started to spread her legs and my hand slid down to feel a dampness coming from between them

My hand then slid back and my middle finger plopped into her awaiting pussy. I pushed it in slowly looking for that dime sized piece of raise flesh. She still just laid there, breathing slowly, concentrating on her own pleasure as I methodically began rubbing her G spot and bringing her to the very brink of orgasm.

" Jason I'm COMMIINNGG!!!" Sam was screaming but I stopped just before her orgasm took over. She looked at me in disbelief and was going to say something, but I silenced it with a kiss. I then repositioned myself and raised her legs by the ankle to watch her pussy spread before me. I kissed each ankle and let my lips brush against her thigh as they traveled to their wet, waiting destination. I kissed her pussy as if it was a mouth, and then allowed my tongue to enter her vaginal canal and then licked up to find her clit. I placed my hands on hers and showed her I wanted her to hold her labia apart for me. I then used my tongue to pressure her clit, pushing against it and fanning my tongue on it as she shuddered. I then sucked it and then blew on it. These three motions were continued over and over, again bringing her to the brink of orgasm. Just as her breathing was about to become an orgasmic scream, I stopped paying attention to her clit and raised her by her thighs a little more, thus position her ankles by her ears. This allowed me to take my tongue and flick it at her waiting asshole. I massaged her tight little hole with my tongue and pushed the very tip inside of her. She had this disappointed but very sexual pout on her face. I knew what I was doing, and ignored her visual plea to cum. I continued to lick her asshole until I knew that if I touched her clit again, she wouldn't cum. I stuck a finger against her asshole and blew on her clit before inserting another finger in her vagina. I began to piston my fingers in and out of her until the wall between them was smooth and thin.

"Are you enjoying this? I want to make sure you enjoy my style. I love the way you taste" I told her as I watched her reach between her legs to grab at my cock. I sat up and pushed the tip of my cock into her wet pussy. I felt her expand and allow me to continue this initial thrust of my cock into her. I was halfway in when I pulled out and decided to rub the tip of my cock against her lips again. She was pouting again so I started the thrust again. This time, I made it about three quarters of the way through and stopped, but didn't pull out, instead I performed a Kegel exercise allowing my mushroom to expand and contract inside of her. I knew this was a tease and after a few of these, I pushed with an unexpected force, the remainder of my self into her. I was enjoying myself to much to pick up the pace and deliberately pulled out and thrust in very, very slowly. I could feel her body's energy and could feel the tension building up inside of her. She was going to cum and instead of it being the usual, she was going to explode. Finally, as my cock was being pulled out, her body stiffened, her eyes closed, and her hands tightened around my forearms. I knew she was on the brink and leaned forward to kiss her ears and plunged my cock into her, very fast now.

"Sam, I want to feel you cum on my cock, want you to explode in everyway, let yourself go and grab, bit, pull at whatever part of my flesh, you bed, whatever, that you want to." As I said this, she bit her pillow, her legs wrapped around my waist and pulled me tight, and her hands moved to pull at the flesh of my back.

"I AM COOMMMIINNGGG!!!" she creamed as her mouth opened and locked onto my nipple and her hands scratched and clawed at my back. I knew I was close to and thrust once more as deep as I could into her hole and let my volcanic spurts of cum paint her vagina as my body collapsed into a heap beside her.

She never asked how I knew she was multi orgasmic, nor did she ask how I knew to tease her into a different feeling she had never had before, but she did continue to enjoy our sessions of passion, whether they were quick, animalistic fucks, or slow, passionate orgasms.