Almost a Virgin

Almost a Virgin

I'm 64 years old, retired for the past two years living in central Florida and loving the good life. A great wife and a nice house and great neighbors. Golf two or three times a week and loving all I have. In reasonable health and my Urologist says I'[m a bit unusual in that I still want and can have sex two to three times a week. I am far from a hansome man and never was but have a good social personality and can talk to people which was one reason I was a very good salesman. My only special tribute that in spite of being probably 25# overweight (working on it without success) is I was blessed with a rather large cock. Ive known this from a very early age as a teen when at 12 or so, the gang and I would sometimes have circle jerks and I was able to cum by that age and even then, sported an 8" cock which blew away my buddies back then. I didn't add much more over the years but have an honest 8.75" using a hard ruler on the top and have just short of 7" in circumfrence. No, certainly not the biggest cock by far but far bigger then most for sure. Enough about me though and now my story which happened just last week.

My wife flew back to our past home area in the upper midwest to be with her aging mother who still lives alone but was having some relatively minor surgery. She would be gone three weeks. My first week alone was really uneventful. I am a good cook but seemed to get invited to neighbors most every night. On Friday, a neighbor couple suggested we go out to dinner at a very nice place. It was Margie's birthday and I readily agreed. Next to them lived Penny, a widow of just four months. Penny is 71 years young and I say young as she is very active physically but she and her late husband rarely went out. Kind of a surprise but Penny agreet to join us for dinner. We would leave at 5:30 and the reservations were for 6:30.

Two hours before we were to leave, I got a call from Marge. Henry was sick. Stomach and intestinal problems sprang up and in spite of really wanting to go, it was not in his best interest for sure. As Penny was really excited by now to go, I called her and suggested just the two of us go. After all, it was only dinner. She agreed and as there was only the two of us, I took my Porsche Boxster and dropped the top. It was a beautiful early evening.

Dinner was great. Food is always excellent in this place and the view of the water was spectacular as we watched people with REAL money on yachts. Penny and her late husband Bob were not outgoing people at all and it was a big surprise to experience how much Penny talked about so much. Like a dam burst at last and she just wanted to talk. And I was there to listen. In all honesty, I was so very glad to do just that. I heard basically her whole life's history in a capsule form. While financially quite successful, they did very little with their lives that anybody could call exciting. Bob was just not that kind of guy. Excitement was taking a boat ride or going to the show and see a movie.

With the excellent dinner came the wine I ordered. Just a glass each but Penny seemed to inhale her glass so I ordered a bottle. Being a gentleman, I kept her glass half full all the time. As sunset was descending, it was time to leave at last. We were both really upbeat and happy with lots of laughter by now, helped by the wine in her I suspect. Top down and the back roads home at a leisurely pace only increased our good mood. A mile from home, I asked Penny if she could join me in another nightcap as I had some good wine chilled and without hesitation, she agreed. We were just in a happy mood.

I pulled the car directly into the garage and shut the door even though it was dark out by now. And while Penny found the bathroom, I opened a bottle of white wine similar to what we were drinking. OK, I will admit, I am a man, wife gone a week and well, I'm thiniking "maybe?" Into my bathoom and before leaving, I took 100 mg. of Viagra. I usually cut those guys in half but with all that wine, well, one never knows. Actually, I chewed the thing and got some under my tongue. Yes, bitter but they work in a lot less time. Just in case.

I slipped on my favorite mood music of late, Rod Stewart Sings the Oldies on the CD player as we just relaxed and continued with our joking and light talk. Probably the third or fourth song and I asked Penny to dance. She was up and on her feet before I was. Just slow dancing and letting the husky voice of Rod Stewart take us someplace else. One dance led to the next and I felt Penny relax and snuggle closer and say she loved to dance but they rarely did. We just seemed to move together like we were one. Penny was an excellent dancer for sure.

As I started out, Penny is 71, perhaps 5'5" or maybe 5''6" and about 120#. She takes aerobics three times a week and is in excellent condition without an ounce of fat on her body. I kind of hate people like that in a way as I always have struggled with my weight. Her hair is died a light shade of red when at one time, she was a natural redhead but mother nature changes all of us. Her skin is so very pale in spite of living in the sunshine state. As stated earlier, they rarely went out. Bob died a few months ago after a two year battle with liver cancer. Before that, about ten years ago, he also had cancer and has his prostate removed and the doctor that did that didn't think he would live then. I found out later that even before that, sex for them simply didn't exist. Almost ten years without sex for her. I later found out that she had given up on any chance of sex again in her lifetime.

As Penny snuggled closer, without any real thought on my part, my cock responded to the closeness and the movement. It had only been maybe half an hour at the most from taking Viagra and already, I was hard. I knew Penny could feel the contact as well as I could and her height was perfect in that my cock was pressing directly on her crotch. Now my mind is racing fast forward and almost involuntarally, my right hand dropped lower and cupped her small ass and pulled her closer to me which she responded to without resistance. Her head kind of lay on my left shoulder and I bent mine to kiss her neck gently and felt her hand tighten on mine. So, I kept it up. Kissing her neck and movig to nibble on her ear, all the while massaging her butt and now trying to grind my crotch into hers. One more song of the same motion and we sat down together on the couch.

Blame it on the wine, the atmosphere, Rod Stewart or whatever but we started making out in earnest as soon as we found ourselves on that couch. Kissing with tongues intertwined as I slipped my hand down to her small but firm breasts, gently kneeding them. Like a clumsy teenager on his first date, my hands fumbled with her blouse until finally, I got it unbuttoned. Taking here bra and lifting up had me looking at very lovely albeit not too big breasts with nipples like pencil erasers, small but very hard. My mouth found first one and then the other as Penny lay back moaning softly. When I released a nipple, my fingers would find it as I'd go back and kiss her neck again then back down, over and over again. At last, when I thought she was really totally into this, I slipped my right hand down between her legs under her skirt which had ridden up quite a ways by now and found a very damp area on her panties. With little pressure, I got her legs open a bit more and slowly rubbed her ever so gently over her pubic area which had her gasping and pulling my head harder onto her breast. A few minutes of this and my finger got under her panty leg band and directly on her cunt which was quite moist. Yeah, 71 and a wet cunt.

It was not easy doing anything but basically rub the outer portion of her cunt because of the panties and by now, I was so turned on, I only hoped she would continue to cooperate. Pulling away, I slid down and reached under her skirt and as she lifted her butt off the cushion, slid down panties that I thought only a much younger woman would wear. Kind of a modified bikini style I guess you'd call them and pink in color. Hell, I really didn't care about them to tell the truth.

Pushing her skirt up and opening her legs a bit wider had my face a foot from her gateway to heaven. I could smell a slight musky odor mixed with perfume and as I took my fingers and gently parted her lips, I could see she was more then just wet, almost running wet. I was now kissing her inner thighs when I heard her voice for the first time. Penny was saying something I didn't really understand or believe. How she NEVER had this done to her before. Is it possible to be married 47 years, three grown kids and not have oral sex? Not have your husband go down on you? I'm sure she wasn't lying as later she told me just that.

In short time, my middle finger was gently probling her cunt as my index finger,forming like a pliers was massaging her clitoris which was much larger then one would expect. I kept my tongue over and around her lips and on her thighs as her legs involuntarally opened wider the longer I did this. Soon, I could feel her hips start to rock in rhythm to my finger thrusting. Ever so gentle at first. Almost like they were afraid to do this. A few more minutes and the thursting was growing so I replaced my middle finger with both the index and middle and my tongue traced the alphabet over her clit. WOW, this really turned her on. Using a come here motion with my fingers, I searched for that elusive G spot and got rewarded with even louder moans and more active hip motion. Her hands were now on my head pulling me hard into her and when I thought it couldn't get any hotter for her, I literally sucked her clit into my lips which had her writhing and moaning all the more telling me to NOT stop and she was cumming. Now, maybe it's just me and the wrong ladies all these years but my ladies cum but never buckest or cup fulls or whatever but they do get very moist and this one was no different. Oh, her cunt contracted hard on my fingers in spasms as her body jerked for several seconds. And I am smart enough to not overstimulate my ladies so I let her clit slip out while gently pumping my fingers in and out of her cunt until she stopped convulsing.

For a second, I was a bit worried as it looked like Penny fainted. Well, she was just totally weak from her first orgasm (I later found out) in so very many years and she said the best she ever had at that. True? Who knows and I just felt so very good to be doing this. Now it was her turn I said and helped her up and to my bedroom. Pulling back the bedspread, I got the rest of her clothes off and sat her on the edge of the bed and asked her to take my slacks off as I removed my shirt. When my slacks dropped, my trapped cock was bulging in my underwear and as she puilled them down, it sprang straight out so very glad to be set free. Now for another surprise from Penny. Her eyes get so big and she just stared at my cock. Then, she said she never saw anything like that. Bob was like half that size and she didn't think that thing would fit in her. She was genuinely concerned and yet, when I took her hand and placed it on my cock, she was just like mesmarized and I knew she really wanted it after what we just did with her.

I just got a sample of KY Gel with warming lotion and never used it as my wife was gone. What better time I thought so lying on my back on the bed, I squirted a liberal amount on my cock then had her get on top. Her head was on my left shoulder and her cunt was above my cock as she lay on my body. I reached between us and positioned my cock on with the head just touching her cunt as she slowly let herself back onto it. There really was no hard time getting this into her. Tight, yes, very. In fact. she slowly let herself onto half of my cock and stopped. She was saying things like, Oh, wow, oh boy, geez, and I'm so full and things like that. Yet, she sure didn't complain. I then was able to move my hips enough to work this amount half in and out for a minute or two and slowly, I worked more into her. Her clit was mashed between out bodies like this and soon, her hips began to move with mine. I'd go up and she'd go down and so on until it wasn't but a few minutes and Penny was again moaning and biting my shoulder now grinding her hips in a circular motion. All too soon, she was cumming again and yes, I was close. A few more strokes and I'd be done myself but I wanted to wait.

She stayed on top of me, just resting for a few minutes and telling me how full she felt and how great it felt until I again moved my hips and started fucking her once more. Very gently at first and in just moments, her hips again were rotating in a circular motion and in less then a minute, Penny was moaning her way into another orgasm. A mixture of a hot cunt brought about by that new KY gel, the tight pressure of her cunt contracting on my cock and a very hot and sexy woman had me use everything I knew to not cum. I had learned a method of anal breathing which helped a lot and kept me from cumming this time but it sure wasn't easy as her cunt felt like a milking machine.

A few minutes of rest and it was now my turn as I pulled her ass to the edge of the bed as she lay on her back. Our king size mattress has just the right frame for me as I stood on the floor between her spread legs, one over each shoulder and entered her this way. Not much clitoral stimulation for her this way but hey, she came three times already. Keeping a steady rhythm of 1.25 strokes per second will often induce a woman to orgasm and in this case, it wasn't maybe two minutes and Penny was now begging me to "fuck her harder". Words I doubt she's ever said before. In this method, I can keep going for a long time and as my cock was by now a lot desensitized anyhow with two close calls not cumming, I kept at it for a long time as Penny came again and again. Not sure but probably three or four more times when I could feel that old but wonderful feeling deep inside moving up, past my prostate and like almost in slow motion, an object moving through my body working to the head of my cock when suddenly, it's half way up my cock and there is just no stopping. By now, I'm fucking Penny as fast and hard as I can and I guess she is whaling away but I'm really not sure as suddenly, I deposit all I have in me at that time so very deep into her.

I usually still cum a large amount and this was no expection and when young, five or six ejaculations was usually the rule, at my older age, more like a dozen or more as I rammed my manhood as deep as I could into her. The look on her face was priceless. Total enraptured bliss mixed with lewdness. Grunting and groaning from her until I stopped and while standing, felt like I need to lay down. Pulling my cock out brought with it a stream of cum which I grabbed my underwear on the floor and stemmed it from running even more on the sheets. Penny just lay with her feet on the floor now and her legs spread with the strangest look on her face I've ever seen.

A shower together and another glass of wine and sitting on the bed naked as the day we were born and Penny tells me she had never experienced anythign like that ever in her life. Never had oral sex. Never a cock like that and in the past, if she'd cum once, well, that was so rare. Never masturbated in her lifetime. Against her religion or so she thought and well, a first for a few things. Well, we still had two more weeks before my wife returns and still a few more things I want to share with her. Is she willing? Well, she stayed the night that night only to walk home two doors down just before daylight.

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