Her Name Was Ann

Story Info
She was 43 year old widow and I was 22.
4.5k words
4.28
138k
16
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Okie-doke. Here is another one of my true stories about past loves or sexual experiences. I still get private e-mails from readers who doubt what I say is true. That's okay. I know they are true and it's somewhat therapeutic for me to write these things here in this forum. My wife and I have talked at length about my wide and wild sexual past and she knows that while I did have a lot of fun, I do have a great many regrets as I toyed with many a young ladies feelings just to quench my own sexual thirst. Writing about them seems to help my guilty conscious.

But not all of my sexual conquests or "counting coup" as I called it, simply dealt with getting my ashes hauled. I actually had feelings for some of the women I have had in my life. This story about Ann Christopher (last name changed) is one of those women with whom I did have feelings, and probably still do to some extent.

As with my other stories, if you are looking for hardcore porn you've come to the wrong writer/story. Yep, sex is here, but it's not every other word.

I hope to hear from you all. Please vote honestly and feel free to leave public comments and/or send private emails. I answer all who leave a return address. Enjoy!

One of my all-time favorite movie lines comes from the John Wayne movie, "The Cowboys". The great black actor, Roscoe Browne (what a wonderful voice he had) and actor A. Martinez were visiting a wagon that had some "soiled doves" bathing and doing laundry. The madam, actress Colleen Dewhurst, asked Martinez's character if he would like to spend a dollar and get laid. To make a long story short, it was determined both men would pass. But Ms. Dewhurst said to the young man (Martinez) that "the first time ought to be in the back of a carriage with someone you think you love". Oh, she was a sexy woman and her gravelly voice sent chills down my back the first time I heard her. Her portrayal of the older madam was the epitome of why I like older women.

The madam in that movie was right. The first time you have sex ought to be with someone you are in love with, or at least think you love. Good or bad, a young man or woman's first experience in intercourse should be fun, romantic and unforgettable. And if it occurs in the backseat of a car or carriage, that's fine too.

I had got my driver's license in 1971 and immediately set about exploring the regions of various girls' bodies in the back seat of my white four-door 1964 Chevrolet Impala. Try as I might, I had no luck in losing my male cherry in the back seat of my "carriage". Then I started dating Krena. She was the same age as me but was a grade behind. Krena was buxom and full-figured. I never liked skinny girls/women and Krena was pretty much how I liked them. Some use the term "full-figured" while others say "corn-fed". I like "Rubenesque"; still curvy with lots of cushion and no chance of getting cut by a thigh bone.

Krena and I played around a lot in the backseat of my old Chevy. She agreed we would have sex but she did not want to do it in the backseat of a car. She had already lost her virginity and it had happened in a car and she did not want to do it that way again. She wanted to "do it" in a real bed. Well, that was okay by me!

Krena and I "did it" only one time, in her bedroom in the middle of the day while skipping high school. We snuck off the school grounds in my car during lunch and drove to her house. I'm not sure the car had stopped moving before I was out and in her house heading to her bedroom. I may have even banged my erection on the steering wheel as I jumped out. Man, I was cocked and ready!

I remember Krena and I giggling as we stripped out of our clothes and hopped into her bed, crawling under the covers and snuggling as we kissed and stroked each other. I crawled on top of her and started stabbing my cock into her. The trouble was I wasn't hitting her pussy! I was so excited (and inexperienced) I was trying to drill my own hole into her pubic region. Gawd but I was a klutz! Krena reached down and grabbed my cock and placed it at the entrance to her pussy. I could feel the warm wetness as my sensitive cockhead felt the softness of her vulva lips. As the rapture of that feeling ran up the shaft of my cock and down my spine, I entered her pussy, sinking to the bottom with little resistance. And I came. Yep, right then on my first stroke into a warm pussy I came. Oh the shame! Oh the embarrassment! Oh the humanity!

I didn't know what to do. So I pulled out, jumped off of her and out of the bed. I stood there staring down at her in disbelief. And Krena did the only thing a girl could do in this kind of situation, cry. Crap....now what do I do.

What I did was I got dressed and left. Oh, I tried to comfort her but I sucked at it. So I made my excuses and left. My first time had been a disaster and I wanted to run away and hide, maybe become a hermit and never show my face to the public again. As I was driving back to school, I knew everyone was looking at me, pointing a finger and laughing. Instead of going to school I went home and went to bed, telling my mom I was sick.

I'm sure my story is not all that uncommon among men. I'm just able to admit that my first time was not my moment of shining sexual glory. I told an older friend of my experience and he gave me some sage advice I have lived by since; learn sexual restraint techniques and always put the pleasure of the woman before your own. Once I learned this, my sexual experiences improved 1000%!

Shortly after this I began my relationship with Shirley East, an older black woman I worked with at the airport (see my other story "Her Name was Shirley"). While we never fucked or made love, we had a wonderful time together for about three months and she taught me many things on how to please a woman out of the bedroom. You know, give flowers, kind words, compliments, things a gentleman should do for his lady. I am forever grateful for her guidance as it benefitted me many, many times over the past 40 years. Even though we never had sex, she helped me advance my sexual skills none-the-less.

In 1976, I met another older woman named Ann. She was white, 43 years old and a widow. She had short black hair with sparse streaks of silver, cut in a "Page Boy" or "Dorothy Hamill" style, brown eyes and a very pretty oval face. She was somewhat elegant without being snooty, and had a refined demeanor. Body wise she was about average; nothing spectacular, other than her height as she was 5'11". Her father had been a state law enforcement officer and she had an 8x10 photograph of him shaking hands with President John F. Kennedy when he was still a US Senator and came to Oklahoma for a visit in 1960 while campaigning for the presidency. She would later give that photograph to me and I have it to this day.

Ann and I met at a local gathering for tall people. It was an informal club called the "Tip-Toppers" and was for men over 6'2" (I'm almost 6'4") and ladies over 5'10". They met once a month at various restaurants around the city. I had been invited by a friend to join and I thought "What the heck. I have to eat".

It was my first time at the meeting and Ann's second or third and we sat next to each other during the meal. We hit it off immediately and soon it was as if we were there alone on a date and everyone else around us was mere noise makers in a busy restaurant. I'm a "toucher" and while talking or laughing I will reach out and briefly touch a shoulder or a hand. At one point, I had said something funny and as we both laughed I put my hand on top of hers. But before I could remove it, her other hand came and rested on top of mine. As our laughter died down to smiles, our eyes locked. I can still see the twinkle of joy that shone in her eyes as the warmth of her hand on mine warmed my soul. We connected at that moment. We had a wonderful hour or so together at the dinner and it seemed like we had known each other all our lives.

As the club meeting began to break up, Ann and I lingered for a bit at the table, much to the waiter's chagrin, I'm sure. We obviously did not want the fun evening to end.

"I like you Rick. You're a very funny and interesting guy. It's a shame I'm old enough to be your mother", Ann said as she lightly rubbed the top of my hand.

"Well, I like you too, Ann, and I think you are an absolute peach. And listen, age means nothing to me. If someone makes you happy, then go with it. Life is way too short to discriminate over something so trivial".

"Peach" is a word I use a lot. I like it. Most women seem to like being called "peach". I don't know why. And what I said was true, she was a peach and life was/is too short to get all hung up on race, or creed or religion or whatever.

To cut to the chase, Ann invited me to her apartment for tea (I am not a coffee drinker) so I followed her in my '55 Chevy (the old '64 was by then long gone). I was looking forward to the possibilities of a pleasurable evening with Ann, both mentally and physically.

Ann had a two bedroom bungalow apartment that was beautifully decorated in earth tone colors with plush furnishings and soft accent pillows. Several candles were scattered throughout the living room and she asked me to light them while she prepared the hot water for our tea.

As I lit the candles, I noticed some record albums she had laid out by her Marantz stereo.

"Oh! You like Herbie Mann?" I asked as I rifled through the small stack of records. Herbie Mann was a jazz flautist that I greatly enjoyed then and still do today.

Ann came around the corner to where I was standing, turning off the lights leaving only the warm glow of the flickering candles.

"I certainly do. Do you like him too?"

"Very much so. I think I have all of his albums except for the ones he did in the 50's. His "Memphis Underground" is probably my favorite."

"Well then, look on the shelf and you will find it. Let's put it on, and enjoy his music, shall we?"

I reached over to the shelf and found the album in quick order and placed it on the stereo turntable as she returned to the kitchen. I stacked five other jazz records on top so we would have a continuous soundtrack going for a while. Moments later, the smooth sounds of Mann's jazz flute began to fill the apartment's airspace. I'm telling you, the Marantz stereo system of the mid-1970's had a great sound to it and looked great as well. The provocative sounds of Herbie Mann and the lit candles began to set the mood for the evening.

I sat down on her plush, pillow enhanced sofa and began to take in my surroundings and the possibilities of the evening. I was amazed at how two hours ago I did not know this woman from Eve in the Garden of Eden and now here I was, alone with her in her apartment and in my mind, obviously headed for an evening of sexual delights.

Ann soon joined me carrying a tray with a china teapot, cups and saucers, sugar and tea bags. The cups and saucers matched the tea pot and had Chinese characters on them with dragons. They matched the wall decoration motif in the living room as she had several items with Chinese dragons hanging on the wall in frames or as tapestries. I made a comment about it and she admitted she had always found oriental art and dragons very appealing.

We sat and drank our tea and made small talk as we enjoyed each other's company. It was amazing all the things we discovered that we had in common. After a pause in our conversation, Ann sat her tea down and again placed her hand on mine.

"Rick, I want you to understand that I don't bring strange men home with me as a rule. And while you and I do share a great deal of commonality, you are still, basically a stranger to me and I do not want you to think I'm some old lady out cruising the streets looking for love."

"Ann, I am thinking no such thing. I am enraptured with you and can think of nowhere else I'd rather be at this moment but where I am, in the company of a charming and absolutely beautiful lady."

Ann leaned towards me and placed her hand on my face, lightly running her fingers over my smooth cheek.

"You are so sweet. But this is all still bothering me and there is the age difference. You're only 22. I'm very concerned abo...."

I raised my hand and placed a finger to her lips to shush her. As I did she stopped talking and looked me straight in the eyes. I could see her eyes were smoldering with a fire that wanted to be either stoked or put out. My next move was obvious as I did not want that fire to go out at all. I leaned into her and replaced my fingers with my lips.

Kissing has always been my specialty and something I greatly enjoy doing, especially the soft, tender romantic kiss. I was very good at it before I hooked up with Shirley East, the lady from my story, "Her Name Was Shirley". I was blessed with a natural style of kissing that pleases women and leaves them longing for my lips. But Shirley helped me to develop my kissing style into a pleasurable art to include what a man should do with his hands while kissing a woman for the first time and it's not grabbing her breast or ass, but ever so lightly caressing her cheek or hair. Jokingly I referred to my kissing as giving the "blue plate special". A great many women fell for me simply because of my kissing ability. There were even women who were not all that fond of me personally who still enjoyed my kisses. Ann was no exception.

As my lips touched Ann's for the first time, I brought my hand up to her cheek and ran my fingers just enough into her hair by her ear to allow my palm to rest on her face as my thumb oh so slightly moved across her cheekbone. My kiss was light and brief and I pulled back a few inches to look into her eyes. Softly, almost a whisper, I said to her my feelings about what she had tried to say before I had cut her off.

"I told you earlier, age does not matter to me nor should it you. Especially now".

I leaned in again and this time really kissed her. I could feel her body yield to mine and move in closer as her arms went around my neck. She turned her head slightly to the side so I could make better, more sensuous contact with her lips. The kiss this time was the "Full Monte" if you will. It was the kiss of lovers.

I lightly tickled Ann's mouth with my tongue, letting her know I wanted entrance. Her lips parted and as my tongue probed the moist recesses of her mouth I found her tongue coming to meet mine. Our tongues danced together and I yielded my advance to allow hers to move into my mouth. Once it was there I closed my lips around it and sucked it in further, feeding on it as if it was a nipple.

Ann groaned as I sucked on her tongue. I would later find out this was a first for her and she really liked it. From that moment on, we did not kiss passionately without her tongue being sucked on by me. She also would suck on my tongue, which I also greatly enjoy.

As various records played, Ann and I enjoyed each other on the sofa. We kissed and panted for at least 10, maybe 15 minutes. Then Ann gently pushed away and held me at arm's length.

"Would you like to see my bedroom?"

I stood up and held out my hand to Ann.

"Yes ma'am. I surely would".

Ann took my hand as I helped her up. But before we took one step, I reached down and scooped her up in my arms. Ann giggled.

"My, my. Aren't you the strong one and so gallant!" she exclaimed.

It was obvious where her bedroom would be since she lived in an apartment so I headed from the living room to the bedroom. When I arrived at the side of her king size bed, I gently laid her down with her head on the pillows. I then moved over her to the other side and lay down with her. Immediately we began to kiss again. Ann made the first move to shed our clothing by unbuttoning my shirt and un-tucking it from my jeans as we kissed. I continued to run my fingers through her hair and caress her face and arms as we kissed. Once she had opened my shirt completely, she ran her hands over my smooth chest and played with my left nipple. As she did so, I began to kick off my boots.

Ann moved on to my belt buckle but had some difficulty with it. It was a large first place bull-riding buckle I had won at a local rodeo back in 1972, the only one I ever won. I reached down and un-did it for her. Ann then unzipped my jeans and reached in for my cock. Oh, it was hard, rock hard. But there was no way she could pull it out without breaking it in half! Remember, this was in 1976 (but before that stupid "Urban Cowboy" movie---gawd I hated that flick!) and the cowboys wore their jeans very, very tight.

I raised my ass up off the bed as I reached down and peeled my jeans and low-rise briefs off. I also took off my socks as I looked back over my shoulder at Ann. She was now undressing as well. I remember thinking to myself, "Hell Slick. You haven't even touched her body other than kissing and here she is taking her own clothes off!"

After I had removed my socks, I leaned back and watched Ann. She had got off the bed and stood at the side of it as she removed her dress, slip, bra and panties.

"Not bad for an old lady I guess" she mumbled.

"Nope, not bad at all. Come here", I said in a sultry but commanding voice.

Ann crawled back into the bed and as our lips met again, my hands immediately reached out to cup her breasts. Her nipples were rigid and pointed at least a half an inch from her pink areoles. She had about 34 B size breasts and while I have always been a big breast man, hers were simply exquisite with very little sag or stretch marks. Hard to belief she had given birth to three kids from the looks of her natural perky breasts and fairly smooth tummy.

For the next hour, Ann and I explored each other's bodies. We sucked and licked each other's breasts, 69'ed and briefly fucked with her on top. While sucking her clit I gave her a wonderful orgasm that had her pulling my hair as she screamed out her pleasure and ground my face harder into her pussy. After that hour, we took a brief break and I went to the stereo to replay the records as they had finished. I returned to the bed and to Ann as Herbie Mann's "Memphis Underground" began to play again. I remember Ann watching as I walked back to her and commenting about how hard my cock was. I responded as I crawled in next to her that it was "so hard a cat couldn't scratch it" which brought a hardy round of laughter from her.

As the laughter began to abate, I moved on top of Ann. My cock was aching to return to her hot pussy. Now, I've been with a few women in my life whose pussy didn't feel that great. But Ann's was not one of those; her pussy was absolutely marvelous. Sure it was a little loose after doing childbirth three times but it felt just fine!

I let my cockhead run along her pussy slit and lightly dance on her clitoris hood. She jerked and smiled, moaning her pleasure at the sensation it gave her. I had to do it a couple more times to watch and listen to her mewl. I then ran it down to the opening and sunk it back into her wet love canal. As my pubic hair meshed with hers, I was in Nirvana. Hot damn but that felt good! There is nothing better than the feel of a warm pussy around your cock when one is engaged in a romantic interlude.

My skills at lovemaking had increased significantly by this point in my life and I was very excited at the chance to make love to this woman. I did not want to fuck her; I wanted to make love to her. Guys, thereISa difference in the two. I've fucked a lot of women, but I have not made love to all of them. Ann was different. This was a lady who deserved respect and my best gentlemanly behavior. I was not going to fuck her; I was going to love her.

I began to move in and out of Ann's pussy; pausing ever so often to bury myself in as far as my six inches would allow and grind our pubic bones together. Ann (like most woman) really liked that as is would rub her clitty against me giving her more pleasure.

12