The Gentleman Caller

My name is Harry; I am a retired widower in my sixties with a high sex drive. For several years, I had a lover but she moved far away and I now had a serious case of sexual deprivation.

Consequently, I went online to use the dating site where I had met her. This was not one of the multitudes of adult sites that were strictly sexually oriented. It catered to singles over 55 who were looking for companionship as well as romance. I chose this site because I prefered older women. From previous experience I knew that within this group there were women who primarily were interested in sex but were too shy to use the other sites. In general, they were grateful for any sex they could, were thoughtful and considerate lovers, and were potentially close friends.

Culling out these women from numerous posts was

tedious because this site did not permit explicit sexual language, but euphemisms and innuendoes were not

excluded. Milly's post caught my eye:

"Who wants to be my Gentleman Caller"

That term intrigued me because it is ambiguous. In parts of our country it can mean a man who discreetly visits a woman at her home for sex on a regular basis. Reading between the lines, her text gave credence to that interpretation.

Milly described herself as a seventy-year-old widow

who craved male companionship. Stated she was an affectionate person and open-minded, but wanted to be treated as a lady. (In other words, she wanted to have sex but had some limits.) She went on to list her many hobbies, plus social and cultural interests. She kept fit going to a gym and by walking. She was a voracious reader and loved traveling abroad but hated doing it alone.

She had attached a family photo in which she was flanked by her two daughters. Two lovely, slender, full-busomed blondes. She was an older model and equally desirable to an older man like me.

All told, Milly was worth pursuing, so I replied by asking her to read my post in which she would find we have similar interests. I proposed that we meet for coffee to explore our compatibility. I added that I missed feminine affection and hoped she might fill that void in my life.

She sent her response a few days later. She thanked me for the email and agreed to meet for coffee. Cautiously, she wrote she would like to learn more about me before making any commitments.

It was a brisk Autumn day. She wore a light raincoat, which she unbuttoned as she sat down at our table, so I could only see that she had on a turtle-neck sweater and skirt, but could discern she had a trim figure. Her gray-tinged blonde hair was swept back to form a bun. She was a very pretty woman with the barest of wrinkles and aging signs. She could easily pass for a much younger woman. I was instantly attracted to her.

Milly proved to be a pleasant conversationist. As strangers do, when they first meet, we spent the bulk of our time exchanging information about our families and interests. I steered the conversation towards sex by asking her why she chose our dating site. As I had suspected, she said the site was less blatant. The others were one-sided. She sought a fuller relationship. She smiled and quaintly said she was still conducting interviews. I chuckled and told her I looked forward to her evaluation of me. The jury is still out she quipped. (I liked her refined sense of humour.)

One of our joint interests provided a hook to sound out her willingness to meet in private. We both enjoyed going to Art Museums and had a particular interest in Oriental art. I told her about my collection of Japanese woodblock prints, which I had accumulated through two tours in Japan as a Naval officer. That sparked her interest, so I extended an open invitation to visit my home. She said she might take me up on my offer sometime. Our meeting ended on that note. I did say I would like to see her again. She agreed to stay in touch.

I really liked her but I did not want to waste a lot of time with an extended courtship, so I composed a brief, polite email:

"Thank you for joining me for coffee. We have a lot in common and many similar interests. You are a lovely woman. I am predisposed to go to bed with you. I hope you will accept my invitation to visit my home. Hugs, Harry."

Usually, at this stage, a woman will accept shortly thereafter or back off and might not reply at all. That had been my experience in internet dating. Milly did not reply for well over a week:

" Thank you for our coffee date. You are a nice man. I accept your offer to show me your art collection. If it is convenient, I would like to drop by your home next Thursday afternoon, around 2PM. "

I confirmed the date and time. I had a plan to get her into bed which would allow her to demure gracefully, if she wasn't of a mind to have sex right then and there.

She arrived on time. We greeted each other warmly in the vestibule with light kisses on cheeks. She took off her light raincoat and handed it to me to hang in the vestibule closet. She was dressed quite casually. A long-sleeved, loose v-neck blouse which revealed deep cleavage, and a simple knee-length skirt. She wore black silk stockings and patent leather shoes with short heels. This time hair was let out and flowed over her shoulders. She looked like an older version of an innocent maiden. I was smitten and told her she looked wonderful. She smiled contentedly.

My home has an open floor plan on the first floor. There is a large 20 by 40-foot living area and an adjacent open kitchen and dining room. A short corridor leads to the master bedroom. Three bedrooms and my office are upstairs.

She spotted my collection of Japanese woodblock prints hanging on three walls of the living area and drifted over to look at them.

"I was very eager to see these. The colors are extraordinary," she exclaimed enthusiastically.

We talked extensively about the prints and the art of wood block printing. She knew a great deal about the influence of Japanese art on the French impressionists. This was the point at which I launched the critical phase of my plan.

"Did you know that some of the early masters made erotic woodblock prints?" I asked.

Her reply was better than I expected.

"Oh yes, I have seen them in art galleries and art books. Do you have any?"

This was the acid test of my plan.

"Yes, indeed. I have a fine display in my bedroom. Do you want to see them?"

She smirked and laughed.

" Harry, That's not a subtle approach to lure me into your bedroom. I would like to see them anyway."

I figured she was being playful, but receptive. I took her hand and led her to the bedroom. Over the headboard of the bed and on two walls were highly stylized scenes of sumurais and geishas fornicating in various positions. Exposed from their kimonas were outsized cocks and hairy, enlarged vaginas.

Milly examined each one carefully.

"They are splendid. The exaggerated size of the genitalia lends a comic relief, but they are arousing," she commented.

At this point I sized her up as a woman who looked to me for directions. I told I was aroused, too. I drew her near me, by placing my hands on the back of her hips. We were about the same height, so our lips easily pressed together for a kiss. She pursed her lips, which I then pried open with my tongue. Her mouth opened and she reciprocated. Her arms had been hanging loosely but she snaked them between my arms to pull me tighter to her. I started to stiffen; she must have felt my bulge.

She was responding, so I told her we should indulge ourselves. I said I was a passionate man and would try to give her a lot of pleasure. I told her I am apt to use lewd language in the heat of the moment. She said she got carried away, too. Dirty talk turned her on.

I sat down on the edge of the side of the bed, leaving her standing perplexed and obviously wondering what would come next.

" Undress for me Milly, I want to admire your body."

"Don't you want to help me," she asked in a hushed voice.

" No, strip for me slowly," I demanded.

"Oh, a strip tease for a one-man audience. My first performance," she gushed, now excited and acting coyly.

She turned around, unzipped and dropped her skirt, wriggling her hips, in the spirit of the performance. She was wearing a garter belt to hold up her silk stockings and black panties. Her legs were thinly tapered and her thighs were slender, and shapely. She carefully gathered up her skirt, folded it and placed it on a nearby chair. Slowly, she unbuttoned and discarded her blouse, folding it, too before placing it atop her skirt. She was wearing a black bra to match her panties. She took her time to allow me a full view.

Turning around, she looked very sexy. I could tell the bra constrained heavy, large breasts. Awaiting my next instructions, Milly looked straight ahead and asked what I thought.

"You look ravishing Milly. Show me your tits!"

The bra had a front clip, which she released. Out flowed one of the nicest set of tits an older woman could ever display. I guessed they were about 38 D's. Sagging a bit, and heavy, quite natural for her age, with large aureoles and partially distended tips.

"Bravo! Millie" I clapped my hands and told her her tits were gorgeous.

"Now drop your panties!"

She turned around again. Removed the bra, which was dangling from her shoulders and placed it atop her clothes. Then in one motion she placed her thumbs in the band of her panties and bent forward to peal them down. in that instance I could see part of her exposed pussy, a full bush. Stepping out of her panties she added them to her pile of clothes.

Turning around, she was fully naked, except for the garter belt and stockings. The garter belt framed her pussy; it was like gazing at an erotic piece of art. Light gray, curly hair and bulging, prominent pussy lips, known as bat lips. She was sex-personified for an older woman. Her tummy bulged and her flesh was somewhat flappy, but was unblemished. Her body was curvaceous and highly desirable.

In a daring pose, she cupped her tits in a mock offering and cocked one hip.

"What's the opinion from the audience now?" she asked in a sexy tone, and she obviously was getting into a lusty mood from her performance.

"Milly, you look magnificent. I adore your body. Stand like that for a moment!"

I hastily stripped, tossing my clothes to the floor. I sat down again and ordered her to approach me.

I was already almost fully erect and could have fucked her right away but I wanted to take full advantage this opportunity.

"Do you like my cock, Millie? is it big enough for you?" (I am a little under six inches erect but fairly thick; women had told me it was just right for their mouths and cunts.

"Your're not as well endowed as a samurai, but it is good enough for me!" she asserted right away.

"Do you want to suck it?"

I watched her stare and open her mouth to lick her lips.

"Go ahead. Tell me you want to suck it!"

"Oh my! I do want to suck your beautiful cock " she blurted out.

Without any hesitation, she knelt between my legs, held my shaft with one hand and cupped my balls with the other before taking the tip between her lips and sucking and tonguing it. She did not deep throat me but slowly stroked my cock until I was very hard and near to bursting. She wasn't a novice. This was the way she had been accustomed to suck off her husband and maybe others.

At my urging, she paused, as I was getting close to cuming. I praised her for how well she sucked me.

"I love sucking you," she said. "Your cream tastes good."

"That's precum oozing out," I told her.

"It's my turn to taste you."

"I'm going to eat your pussy."

"Oh, I love that! It gets me really hot, "

Very adroitly, she rose and flung herself on the bed on her back. She raised her hips for me to slide a pillow under her ass for full exposure of her pussy. She then quickly drew her knees to her chest and spread her legs wide for maximum access. This lady was accustomed to pussy eating.

Her pussy was so soaked with her juices, it would not take much to get her off. I did not delay. Palm upward, I thrust two fingers inside her. Curled them to rub against her G Spot and rapidly tongued her already swollen clit. The sudden onslaught sent a shock across her nervous system. She began to tremble and moan louder and louder. I looked up to see her arms spread wide clutching the sheets. Her head was twisted to the side and her facial features were contorted.

"Oh my Gooood," she shouted, as she climaxed, extending the word God for many seconds.

I kept licking her clit to learn if she was multi-orgasmic, but she began to sob, pushed my head away and cried: "It's too much, too much. I can't take any more."

She then curled into a defensive fetal position.

I am ashamed to say that her climax caused me to have a pre-mature ejaculation. Not a full discharge, so I knew I could recover in about twenty minutes.

The way she was lying curled up, I was able to snuggle up along side in the spoon position. She was coming down from an orgasmic high, still trembling. I could feel her body heat. I nestled my limp cock along the crease of her ass, lightly carressed her tummy, kissed her neck and told her how sexy she was.

In a voice trembling with emotion, she said:

" That was wonderful. I loved the way you warmed me up. I felt entirely uninhibited."

"Do you always cum that hard? I asked.

"Sometimes when I am very aroused. My husband once thought I had fainted. He got used to it. The French call it le petite Mort, the little death."

When was the last time you had sex?" I asked, thinking maybe she climaxed so hard because she hadn't had sex since well before husbands death.

I was startled to hear her say:

"Ten days ago. It was very disappointing," she added.

At first she was reluctant to elaborate but in bits and pieces told me the essential facts. She had interviewed three men before we met for coffee. She rejected two and met the other one in a hotel room. Against her principles, he was married, but he was locked into a sexless marriage with a gravely ill wife. She felt sorry for him and thought they could give comfort to each other. When she entered the room, he embraced her and hardly spent any time before penetrating her in the missionary position. He finished soon thereafter before she could get aroused. He apologized for his haste. She felt humiliated and used. She left immediately. At home she received a text from him thanking her for the sex. He felt guilty about the whole episode and had decided to bear with his marital situation. She realized it was an unusual situation. It did not deter her from trying her luck with other men.

That explained why she held off meeting me at my home. I was the next man on her list. That did not bother me since I was the first to give her pleasure.

Through her body heat and the sex talk, I felt aroused enough to fuck her.

"Do you want me to give you a proper fucking," I asked her softly.

"Oh, please. I want to feel you inside me."

"What position works best for you"

"From the side. Like now, so you can play with my tits and clit."

My cock was already hardening in the crease of her ass. It took only a slight maneuver to enter her juicy pussy. She was loose but she used her inner muscles to grip me tighter as we slowly fucked.

Her moans increased as we fucked and I alternated plucking a nipple with fingering her clit.

I could not hold back, so I warned her I had to cum.

"Yes, cum for me! Go ahead!" she urged.

At the same time she brushed my hand away from her pussy and began to vigirously rub her clit. We raced to cum, and I won.

"Holy shit," I shouted as I burst.

it wasn't long before she came again. As before, her body spasmed and she screamed out her pleasure.

I collapsed on my backeand gasped for breathe. She sobbed and nestled beside me, her arm over my chest.

"You really fucked me properly. We are a good match," she whispered.

"Better than I could have imagined, " I replied

Will you be my Gentleman Caller?

I was hoping you would ask."

We kissed passionately to seal our bound.