This story takes place in the summer of my 19th year. I had returned to my hometown after an accident which had left me hospitalized for two months. Upon returning I needed to determine a direction for my life. I had enlisted in the army and was awaiting my active duty date in late 1969 when the accident happened. The damage to my body was sufficient to cancel my enlistment and give me a get home free pass from Uncle Sam’s party in Viet Nam. While many of my friends had suffered as a result of that war, I was not sorry that I did not have to go.
So here I was, back in town and not sure of what to do with myself, the band that I had been in before I left for the Army was still together and upon contacting them I was welcomed back with open arms. We were all around the same age and single so we decided to rent a house together so that we could devote much time to practice and recording. Earlier that year before my enlistment, one of the members of the band arranged for his mother who was a tailor to make some show jackets for us. I had never met the lady before and so I was amazed to see this petite woman of 37 (at the time) and pleased at the same time. We had to go to his parent’s house to be measured and then fitted for the jackets. Each time I went for a fitting, his mother would be very pleasant to me and offer me a soft drink, the last fitting took the longest as she kept fussing with seams and re-sewing things as I watched and waited for the “try this on now” that came after every adjustment.
Alice (not her real name) was petite as I said, 115 lbs. Slender, with about 32C breasts and a tiny waist. Each time she bent over to tug on my coat and make sure it hung right, I tried to see down her blouse but to no avail. Now, months later, the experience of a lifetime was just ahead for me. The band had moved in together, and her husband had moved out to live with a much younger woman. So, it was not unusual for her to stop by the house and play house mother to all the boys in the band, making sure the refrigerator contained some healthy items in addition to beer, and that we were all in good health. It was on one of these such visits that she was sitting in the kitchen and her demeanor was anything but the usual chipper smile we were all used to. It seems that she had just found out that in addition to moving out with this young lady, her husband had been carrying on for sometime with some others along his travel route on the road. He was an outside salesman for a line of goods that were sold primarily to women so he had a number of places he could play along the way.
The dark clouds over her head did not seem to be showing any promise of lifting as I pulled up at the table. Her son Tom was across the table from her shaking his head and she was saying.
“I just wish I had someone that I could go out and have a couple of drinks with, but I just don’t know anyone, I have spent way too much time at home for the last few years.”
Tom said, “Maybe that would be good if you could just go let your hair down some, and have more than just a couple of drinks.”
“Well,” she said, “I am not going to go anywhere and have anything alone, that would just make me feel worse.” “Talk about pitiful,” she continued, “out drinking by yourself after your husband has run off.”
I had the feeling that I needed to add something positive to the conversation so I interjected. “Hell, you might start out the evening alone, but I doubt with your looks that you would stay that way for long.”
Tom looked at me in a bit of surprise after what I had said, and Alice replied, “That’s sweet of you to say Stan, but I don’t want to end up with anyone I don’t know at the end of the evening, and that is probably what would happen given my present state of mind.”
Now it was my turn to look surprised, but not as surprised as I was about to become. Tom really gave me a start when he turned to me and said. “Stan, why don’t you take Mom out, you look old enough to get into a bar, you do it all the time, and she would be safe with you.?”
I didn’t really know what to say, she was looking at me and waiting for an answer just like Tom was, although there was a hint of a smile on her face for the first time since I had seated myself at the table with them.
“Well, I suppose, if Alice would like that, we could go to Santa Cruz this evening .” “I have no plans and we are not booked anywhere for two more weeks.” I smiled at her and said, “It would be an honor to escort the prettiest lady I know out for some drinks.”
“And dancing?” Alice smiled a bit more.
“I think I can find us a place to do a bit of both, if you like.” My mind was running away with itself, her attitude seemed to improve greatly, and the fantasies I had often entertained with her as the featured player while masturbating were colliding behind my eyes so vividly, it was hard to conceal my growing erection.
There was a time agreed upon and in preparation for the evening, I had to remind myself that this was Tom’s mother, and not some date that I had an opportunity of scoring with, over and over I said it to myself, but that did not stop me from continuing to prepare with the shadow of hope in the back of my mind. As the appointed time approached, I was positively aching with the hope that I might have another shot at an older woman.
The doorbell sounded distant, it was a cool, but not cold, California summer night, the sun had just set, and the smell of freshly cut grass permeated the air after the Saturday afternoon gardening and watering that took place in most of the neighborhoods like this one. I was not prepared for what I saw as she opened the door, and the look on my face must have spoken volumes. “Is everything alright?” she asked. “You look incredible!” was all I could manage. Her laughter was delightful and she said something about that being a good reaction and handed me the keys to her Cadillac. I had learned early on that, not only do ladies like to have their door opened, but when you did, you got the opportunity to enjoy viewing legs at their finest….and hers were fine. Encased in sheer nylons under a shorter than normal black skirt with a white peasant blouse worn off of her shoulders, she looked good enough to eat.
Closing her door, I moved around to the driver seat and after getting things adjusted to accommodate my 6’3” frame, inserted the key in the ignition, started the car and backed out of the driveway. We were just a driveway away from her house when she said. “Let me see if I still remember how to do this.” And slid across the seat next to me. “After all,” she said “if this is to be a proper date, the girl does sit next to the boy doesn’t she?”
If this is to be a proper date I would be hoping for much more, is what I thought. What I said was, “I don’t think you have lost your touch at all.” Looking down at her dainty feet held together on hump and the skirt that had ridden up her thighs enough to give me a real desire to see more.
“I am happy to hear that,” she said “I was really concerned that I might not be what you wanted.” And after saying that she placed her hand on my thigh and then slid it down to a position that allowed her to place her elbow on the bulge in my pants and sigh contentedly.
During the half hour ride to the coast, we made small talk about the band, and about new outfits that we might have her make for us. She giggled as she talked about the various fittings she had done, about how every one of the guys were nervous and fidgeting except for me….she laughed and said that when I first walked into her living room to be measured that she had thought to herself how much she would love to measure me for a pair of pants too, and that she had scolded herself for her thoughts. I was looking down at her legs now and her delicately crossed ankles as she looked up at me. “I feel safe with you, but I don’t want to, I have wanted to be alone with you from the first time I touched your body.” She looked down at her hand, and squeezed my thigh as she said this.
“You have no idea how many times I have wanted to be in a situation like this too.” I said shutting off the engine in the parking lot of the Bar we were headed for. Turning to her I asked, “May I do something I have been dying too all evening?” She nodded as I leaned down and brushed her lips with mine, my tongue slipped between them and she took a deep breath . My hand, which had gone behind her neck to tilt her face toward me now went down across her bare shoulders to find her right breast and gently stroke the nipple through her blouse and bra. Her kiss became far more animated as I let my had trail lower and lower finally slipping up under her skirt on the inside of her left thigh and, as they opened, to the mound at the top. The heat between her legs was evident, as was the moisture, when at last our lips parted she said….”I think it is time for that drink now.”
Two drinks later we were back in the parking lot, she had resumed her place next to me with the subtle difference that now her right hand was in my lap caressing and rubbing my hard-on as she kissed my neck….”Make love to me on the beach.” She whispered against my neck. While the idea was one of some merit, summer evenings at the coast are seldom warm enough for that kind of activity.
“Sand gets into everything, “ I said, “How about a room?” Of course she agreed, but what she was not aware of was that I wanted to remove her clothes and enjoy her body, her entire body, and for that she needed to be in a motel room and nude.
I was nervous as I went into the office of the Motel on Ocean, but the proprietor was very quick on the uptake. Looking out the window into the Cadillac and the very visible legs in the front seat, without looking at me he said. “You want a room for two with a queen bed.” Not a question, but a statement, to which I replied, “Yes sir, thank you.”
Second floor, no luggage, turned on the TV for the glow and we kissed again, and again, and again, then pulling her blouse over her head, she walked around the bed and after pulling the bedspread back, laid down and held out her arms to me. I stood next to the bed, removed my shirt and stepped out of my loafers. Next, I unzipped my pants, and pulled them and my jockey shorts down, stepping out of them. I looked back at her as I straightened up. I had been ready to enter the military, 195 lbs. Well muscled from push ups and sit ups, broad swimmers shoulders, tapering to a narrow waist, she was positively drooling as I stood there. Laying down next to her, we kissed again and as I nuzzeled her neck, I reached behind her and unhooked her bra, leaning up long enough to pull it from her arms, and appraise her small breasts with the silver dollar sized areole and the nipples that stood up firm and proud as I bent to tongue each one individually, once again proving that smaller breasts are often more sensitive. Soon she was shedding her dress and panty-hose as quickly as possible yet not moving her upper body from the ministrations of my tongue. I continued downward, nibbling and licking her stomach, kissing my way down to her triangle of hair…as I reached it, I moved into position between her legs and began to kiss the inside of her thighs. Torture can be a good thing when done with soft lips and tongue….her moans were increasing as I drew nearer her center, kissing her outer lips, gently sucking first one and then the other into my mouth, she began to open like a flower. “Oh, God!” She said “He never does that for me.” “You are amazing!” “Ohhhhhhh, please, just a little more….just a little more….ohhhh, unnngghhhh.” Her moans turned into breathless grunts as her first climax shook her to the core. Then, before she had the time to come down completely, I took her back up to the top by engulfing her clit with my lips and tickling just the tip of it, inside the hood, circling it round and round with just the tip of my tongue until the sounds that were emanating from her throat were nothing but a series of animalistic grunts ending in her legs shuddering and shaking. Her pussy was wide open now, convulsing, desiring to be filled….she was in the throes of orgasm as I moved my mouth back up to her breast, her breath, a sudden rushing intake of air as I bent almost double in order to keep her nipple in my mouth and impale her with my cock.
The silken opening of her lovely center, closed around me as she felt the length of me delving into her depths and pressing against her cervix….”I see why all the girls love you.” She breathed as she arched her back and pressed her pubic bone down against my cock. Her pubic bone was almost painful as she rocked it back and forth on me dragging herself from one orgasm to another, milking me with her internal muscles, she hooked her heels behind my thighs, urging me on to a faster pace. Pounding into her, she began to cling to me, holding me deep within her…breath ragged, whispered words of encouragement, riding me for all she was worth, faster, harder, her pubic bone moved to a different angle to allow for the deepest possible penetration. Harder, her heels drummed against my ass, I placed my elbows above her shoulders to hold her in place as I began increase the speed of my drive into her….harder and harder….deeper, faster thrusts, against me….”ungh, ungh, ungh, ungh, ungh, ungh, the orgasm is coming….hot, hot, hot, so hot, gonna cumm, gonna cum hard, Oh my God!” She was crying, whimpering, biting into my shoulder as she screamed in order to smother her voice, and then collapse, she was unconscious, and I was terrified. I pulled my now soft cock from her body, it was not soft because of my orgasm, I had not had one yet, it was the thought that I had killed my friends mother that drained the blood from my cock and my face. I had no idea what to do, I knelt over her and stared at her, she was breathing, I began to breathe again too. With relief, I noted that she was not dead, I turned around and leaned back against the head board, then I got up and removed my cigarettes from my shirt. My respiration had begun to return to normal as I lit the cigarette and drew the smoke deeply into my lungs, leaning back against the headboard again, she sighed and rolled over against me.
“That was the most intense sex I have ever had in my life!” She said. “Where in the hell did you learn how to do that?” I smiled and said, “well, you are not actually my first older woman, but you certainly were the hottest.” This drew and interesting look from her, as she leaned up on elbow and looked at me. “Really?” She said, “So what have these other older women done for you in the past?” “I am not sure what you mean.” I said, and then, leaning down she breathed on my cock and asked…”Did they ever do this?” As her hot mouth closed around my now stiffening cock, I felt the head hit the back of her throat and then I felt her throat open up and I looked in awe as knealt above me and deep-throated me….she did this before Linda Lovelace’s unique talent was immortalized on the big screen. I have the ability to hold back my climax for an incredible amount of time and I was doing so now. She looked into my eyes as her mouth traveled up and down my seven plus inch cock, it glistened with her saliva, and as I smiled at her and enjoyed what she was doing, she began with renewed determination until finally, I decided to let it all go, I began to take deep breathes, the hyperventilation leading to the lightheaded feeling of impending orgasm, then with a low groan I filled her mouth and throat with my fluids, she moaned and licked and slurped and swallowed, then without removing her mouth from my cock she laid back down on her side, with her head on my stomach and my cock in her mouth. Only one word escaped my mouth in answer to the question she asked prior to engulfing me. “Never.”
This story, like my last one, was taken from my life, the experience, time and place are real, only the names are different, there were several other adventures with Tom’s mother that happened over the next year, some very erotic, some leading to other erotic adventures, I hope you liked it, and send me some feedback. Thanks