I have often pondered the manner in which society has changed in its view of sexual relations over my lifetime.
It is now quite accepted that older people, for example grandparents, still enjoy sex. It has not always been that way. There is no doubt that Grandparents used to to do it back then, but it was simply not acknowledged. Today of course, one could make a date with a grandparent online and be screwing that evening.
I learned about mature sex from an older woman when I was about 21 years old. They say that men’s brains differ from women’s in the way they store memories. While women’s memories are totally interconnected by a maze of internal wiring, men put memories in little boxes in the brain, each one more or less separate from the other. Let me tell you about the contents of one of my little memory boxes, which I open periodically and relive with much pleasure. The events remain as clear to me as if they had occurred yesterday.
My best friend Cliff and I attended a small technical college. This particular year we were returning for the final semesters following a summer’s work experience. We arrived a little too late to acquire one of the preferred boarding houses and had to search for another. Options were limited in this modest sized town.
We were provided names of a few people that were ready to consider boarders in a neighboring town about five miles distant from the college. It was not a bad arrangement as there was a connecting bus service. We called one lady who suggested we come over for an interview.
Her name was Dorothy Chalmers, Mrs. Chalmers to us, and she was a widow now living alone in a rather large house. She greeted us at the door and invited us in for tea. She was a nice looking lady, petite in size, hair tied in a bun, quite formal and very much in command of her surroundings. She wore some sort of foundation garment, her hips torso and breasts rigid beneath her dress. She was probably between fifty-five and sixty and while I now recall her as attractive, there were no erotic thoughts in my mind at our first meeting.
She told us that she had raised five sons and preferred male boarders. She would cook all our meals and lunches, provide us with a single room each, do our washing and generally do all that our mother’s had done. She would not stand for any drinking or bad language in the house. We were expected to help her with the heavier household chores such as fuelling the furnace and wood stove, and snow shovelling during the winter.
The main floor of the house consisted of entrance hall, kitchen and dining room. There were five bedrooms upstairs. The master bedroom was centrally located on one side of a hallway with a smaller bedroom each side of it. There was a double locked door between the master bedroom and each of the smaller ones. Cliff and I each had one of these smaller rooms. They were great rooms set up as they were with a desk and lamp for study and most importantly single occupancy.
There were two bedrooms on the other side of the hall with the main bathroom and toilet in between. These two rooms were reserved for family visits, one of which was for Mrs. Chalmers alcoholic son who showed up a few times a year during those rare occasions when he was on the wagon.
She accepted us as tenants and we moved in that evening and settled into our new routine. One of the benefits of living in this town was that there was less competition for ladies from our fellow students, our school being an all male institution. Within a few weeks we both had steady girl friends; by far the best way to get through a school year.
Mrs. Chalmers was all we had hoped for. She looked after the two of us like a mother hen and the food was excellent. There was no curfew but she was there at the door every night when we returned home. She kept the door locked but made no issue about the nights we were a little late, just smiled and let us in.
During the day she always wore dresses or skirt and blouse. At night she wore a long nightgown covered by a heavy robe. The only obvious difference between night and day was that in the late evening she was without her foundation garments and her real body was visible moving beneath all the gowns and robes.
I was getting pretty hot and heavy with my new girl friend, but aside from a lot of heavy necking, I was not yet even close to getting any pussy. She claimed that she had a very thick hymen and would have to have it operated on before she could have sex. Still don’t know if that was the truth. All I know is that only my fingers and tongue got to feel it, the pussy that is. In my desperation to encourage her to relent, and by means of trial and error, I discovered oral sex and became quite adept with my lips and tongue.
Needless to say I returned home each night with a pair of aching balls. I suspect that Mrs. Chalmers could sense my problem when she let me in each night. She was one of those people who saw and heard everything and after raising five sons most likely recognized my symptoms as well as the problem.
On many nights I relieved the pressure by getting myself off. This raised certain problems as Mrs. Chalmers was also doing the laundry which included my shorts and the bed sheets. While still living at home I had devised ways to get myself off without leaving signs. And so now when the need became unbearable after a hot night with my girl friend, I would cross the hallway in the dark to the bathroom and do the dirty deed.
Gradually I became more aware of Mrs. Chalmers as a woman and I am certain that she started to entertain thoughts along the same lines about me as a man. She had pretty well done away with the long night gown under the robe. She was so aware of everything going on around her that she had to notice my eyes on her cleavage.
My half crouched entries each night would certainly alert her to the fact I had a bone on and her eyes drifted down and lingered at my groin. She would lay a hand on my arm as I entered in that sort of touch I later learned was a female signalling interest. One night as I passed her in the doorway, I bumped her hip with my cock. She did not pull back but stood firm as I moved past.
Cliff was off with his girl for a weekend on one occasion. That night as Mrs. Chalmers met me at the door, we lingered longer than usual and chatted about nothing in particular as I recall. I believe we both wanted more but neither had a clue how to get it.
Later on after I had been back in my room for half an hour or so my balls were aching and I was still hard. It was fairly late so I did not think Mrs. Chalmers would be awake as I crept across the hall to the bathroom to jerk off. I had to do it to get some sleep. Just as I was at the bathroom door I heard, “Jim, just a moment, let me help you out.”
I was stunned momentarily. She said, “Go back to your room and I will be in there in a minute.”
I did as requested, the part of me that required help was making a tent in my shorts. I sat on the bed until Mrs. Chalmers returned carrying a wash basin and towels. She was wearing a skimpy robe and displaying a more daring cleavage than normal. She set the basin and towels down and motioned me to lie back on the bed.
Her hair was loose around her shoulders and her eyes were very soft and tender. She reached out and moved her hand along my chest and sides and belly. She said, “You have a nice hard young body, I like touching you.” She put her hand on my shorts and rubbed the palm of her hand along my cock which was tight up along my belly with the knob trapped under the band of the shorts.
She pulled the band of my shorts down to expose most of my cock. She said, “You know what I am going to do for you don’t you. I want to relieve you with my hands. I am doing it for myself as much as for you. I have heard the sounds of you getting yourself off for weeks now and it has excited me.”
She slipped her hand down along the bottom of my cock right into my shorts until her fingers found my balls. “You like that don’t you. I can feel you tense and react, you are thinking of getting off aren’t you. I love the feel of you, so hard and urgent like only a young man can be.”
She stood up and I lifted my ass up as she pulled the shorts right down. She took a towel and slid it under my ass. What a weird situation, but I knew whatever would happen it would be pleasant. I gazed at her body, searching for signs of her tits showing or seeing her pussy in the robe opening. But she was quite careful and did not permit them to become exposed.
Sitting beside me, her hand circled my cock and stroked it gently. She teased my knob by making little circles around the ridge with a finger. I could see her tits hanging under the robe, she was definitely not wearing a bra. I spread my legs when she moved to feel my balls. She seemed fascinated at how my cock would surge upwards each time she held my balls in her hand. I had the feeling that I was about to enjoy my first blow job, but she did not make a move in that direction.
“You are close now, I can tell, lay back and let it happen, let me know when you are ready to get off. You are so hard; it feels as if I have a bone in my hand, a bone covered by warm flesh.”
I just lay back and surrendered to pleasure with my eyes closed. I reached inside her gown as she leaned over me and held a tit in my hand as my body writhed in pleasure. She did not attempt to stop me and in fact her hand squeezed my cock more tightly and I began to cum. I gasped “Here it is.”
She dropped a wash cloth over my knob and kept stroking. I arched my back up and let it fly. She clasped my cock just below the knob and held on as the last of cum surged out. She cleaned it off with the wash cloth and then retrieved the basin. Wetting another cloth in the warm water she washed my cock and balls and then dried me off. I could tell that she was very aroused although remaining extremely diligent in her task.
She gathered up all of her gear and stood up ready to leave. She smiled down at me, “I could tell that you enjoyed that, as did I. Maybe we can do this again another time. If you want me to come back again some night, just leave your lock undone. I will know and if I am in the mood we can pick this up again.”
The next morning at breakfast, she was all gussied up again in her corset or girdle, her hair in a bun and basically all business. She gave no indication that she recalled jerking me off just a few hours prior. I remember having quite mixed feelings through that day. On the one hand a feeling of exhilaration that a woman had wanted to get me off like that. On the other hand, I wondered what sort of man I was to feel good about a grandmother jerking me off.
I took my girl out that evening. We spent some time in the hallway outside her parents’ apartment. We were at that stage in our relationship where our first move was to take her tits out and remove her panties. This night I slipped my cock between her legs and we enjoyed a standing dry fuck. There was no penetration although I was convinced that I could have parted that thick hymen.
I returned home to Mrs. Chalmers in a similar state to the previous night. She greeted me at the door as usual. She was wearing the same light robe and her hair was loose and flowing around her shoulders. I did not see a landlady or grandmother, just a very desirable woman.
I returned to my room and heard her follow a few minutes later. When I heard her enter her room, I went over and unlocked the connecting door, and then sat on the edge of the bed and hoped. The door opened after a few minutes and she entered with the wash basin and towels once more. She was more careless about the robe and as she approached I could see the valley between her tits.
I said something like, “Oh damn Mrs. Chalmers, you look beautiful tonight.” My eyes were fastened on her breasts as I spoke.
She said, “Call me Dorothy when we are alone like this. I want to be more like your lover than your landlady. I have been thinking about you all day and was pleased when I heard the lock click. Take your shorts off and lay back again. I want to feel you again with my hands.”
She settled down beside me on the bed, sort of sideways to me with her feet still on the floor. Her robe parted and I could almost see a nipple. I was thinking of fucking her but ready to accept whatever pleasure she had in mind for me. I guess I was still intimidated by her and was having a difficult time separating this night person from the day time version.
She let her hands roam my body as she had done the previous night. “I love to touch you, all of your body, love the feel of your muscles beneath the skin.” The palms of her hands were very hot and her fingers played delicately with my nipples and groin. Her hand hovered over my bush teasing the ends of my hairs. Then she rubbed the flat of her hand along the bottom of my cock shaft, up and down, then to my balls and back again.
She reached over and took a warm wash cloth from the basin and returned to wash my balls and cock. My mind went back to my encounters with two hookers I had laid a few years previous, and how they washed my cock off before fucking. Dorothy was no hooker but the similarity was there and I wondered if this meant I would get to put it in her pussy this night.
But she had other plans, and I soon realized that my first blow job was close at hand. She leaned over me while holding my cock like an ice cream cone. Her robe parted and I felt a nipple brush my chest before I felt her breath on the end of my cock.
I am sure I leaked a bit of pre-cum before her tongue tip found my knob. She circled the knob with her tongue, and then slowly lowered her lips around the knob. I had no idea what I was supposed to do. Should I push my cock into her mouth? Should I take hold of her head and guide her? I did not want to cum yet so I took my mind off it a little by finding a nipple with my fingers. This seemed to arouse her even more and her head began to bob up and down. I had never had such a delicious experience in my life and I am sure that my toes curled in sweet agony.
After a minute or so she lifted off of me. Still holding my cock in one hand she moved her upper body to present a bare tit for my mouth. “Ah God, I have been thinking of your mouth on me since you touched me last night.”
I rubbed my face on her hanging tits, and used my hand to bring an erect nipple to my lips. It felt quite different in my mouth to the flatter nipples of my girl friend. These were full and rubbery to suck and Dorothy’s body reacted to my efforts in a much more dramatic fashion.
As I moved from one nipple to the other, my free hand slipped between her thighs and up to her pussy. She spread a bit for me and my fingers found her panties. I rubbed her mound to excite her, and then slipped one finger down between her legs. She spread more and I managed to push the panty to one side and find her bare slit. Her arms tightened around my head as I continued trading nipples with my lips. I felt her raise her upper leg to open and allow me to slip my finger into her. She groaned and said, “What do you want to do to me?”
I was a little taken aback, to me it was obvious what I wanted to do to her so I said, “You know what I want to do to you.”
“No, no, tell me with words what you want to do.”
I had never heard Dorothy even say “damn” in the time that I had known her. And on both occasions including this one where we were feeling and sucking each other, she had never referred to her own tits or nipples or my cock with a word other than “it”. She was almost trembling in anticipation of what I might say. I guessed right and said “I want to fuck you Dorothy.”
She clenched me tighter to her, and I could feel her pussy closing and releasing my finger. I began to finger fuck her and her ass responded by joining in. But she suddenly pulled up closing her legs and said, “Not tonight, we have gone far enough, I need more time.”
My disappointment was short lived however as she immediately went down on me again and took my cock in her mouth. She bobbed a bit and then said, “Let me know when you want to get off, I don’t think I want to swallow it.”
After a few more bobs I tapped her on the shoulder and said, “Here it is Dorothy.” She pulled her lips off my cock and managed to get the wash cloth back over the knob as I blew my load. She continued to hold my cock as if she did not want to let it go. She was still aroused. She seemed frozen in time and finally I pushed her onto her back. She looked away shyly as I viewed her partially exposed body.
I said, “Let me do something for you Dorothy. Surely you want to get off. Let me do it.”
She said “Okay, yes, get me off with your fingers.”
I opened the robe and lay on my side and went back at her tits and pussy. I pushed two fingers into her and started to finger fuck her I said, “Would love to put my cock in you Dorothy. Love to put it in your cunt and get off in there. I would get on top of you between your legs and your hands could hold my ass and you could dig your fingernails in my butt.”
Dorothy was almost crying, with her body trembling and legs shaking as I fingered her. “It’s been so long, I am nervous about doing it again, I want you in me but not now. I have to think about this.”
I closed my lips on a nipple and fingered her relentlessly until she let herself go and had an earth shaking orgasm. We lay there a while totally spent. I reached for the wet cloth and washed out her pussy.
Before she left I said, “We have to do it Dorothy, when will you decide?”
“If my door is unlocked some night when we are alone in the house, you can come in and join me in my bed.”
My partner returned the next day from his weekend, and there were no more exchanges between us for some time. I did leave my door unlocked every night just in case she might be willing to sneak in and give me a hand job. But she did not. Through the day Mrs. Chalmers remained as stiff and proper as ever. Only I knew of the molten rivers running deep within her.
It was almost a month after our two nights together that Cliff was away again for the weekend. He and his girl were very close to becoming engaged and her parents were attempting to get to know him better. The night that he left I said goodnight to my girl quite early, claiming a head ache. I had an ache alright but it was not in my head.
Dorothy was at the door as usual when I returned to the house. Her hair was down over her shoulders and her light robe open enough that I could see most of her tits. Her eyes were smoking hot when she said “I am going to my bedroom now.”
I was in my room within seconds of her and I stripped down to shorts. Her door was unlocked as I knew it would be and I entered her bedroom. The lights were off and she said from the bed, “Leave the lights off Jim, I prefer not to have them on.”
I stood beside her bed. I could make out her body in the dim lighting, enough to see the dark aureoles of her nipples and the black triangle of her bush against her milky white skin.
I said, “I am going to fuck you tonight Dorothy. If I get on that bed with you there is no turning back.” The only sound was her breathing as her legs spread slowly. It was obvious that my coarse words were exciting to her. I guessed that she had never said them out loud herself and found it a turn-on to hear them addressed to her.
“My cock is hard Dorothy; I want to rub it between your tits and then drag it down your belly and put it in your cunt.” She was almost whimpering in anticipation.
I crawled up between her legs. She raised her knees with her feet flat on the bed. I kissed the inside of her knee then licked my way down her inner thighs.
“Oh no, what are you doing?”
I was nuzzling her bush with my chin and nose and then slipped my tongue along her slit, licking and pressing it at her. I felt her arch her back upwards, wanting more. But I continued my way up her belly to her tits, licking away, sucking and kissing. I crawled up further on her, dragging my cock and balls along her belly until my shaft was between her tits. I used my hands to fold the tits over top of my cock and I screwed them for a minute.
I moved back down between her legs and worked my knob into her slit. She was quite tight, probably from nervousness, so I held the knob just inside her cunt lips and let her work her way onto it. I felt totally in control which was sort of strange giving the fact that this woman had more experience than I.
She began to loosen up and her hips began driving up at me. We began to fuck in unison. “You like to be fucked Dorothy, you love a hard cock in you, get off with me, take my juice.”
I could feel Dorothy settle in now, her entire body released to the pleasures of sex and I experienced for the first time what it was like to fuck a real woman. I had been in bed with two hookers whose strategy was to get me off as quickly as possible, which they accomplished. In addition I had frantically fucked two younger women who knew even less than I about pleasure.
But Dorothy was on another level to any of them. She adjusted to my desperate stroking, in some way calming and encouraging me to slow down. Gradually our bodies seemed as one and I could feel hers melding with mine. Her legs gradually encircled my torso and her heels clamped down on the back of my legs. Soon she caught up to my desperation and began to encourage me to cum in her. It was she who was doing the talking now and me following the instructions.
“That’s it Jim, rub it in me, go deep and get me off. Hold, hold, let me have it, let me squeeze it, oh goodness, now, now.”Her body stiffened and shook as soon as the words were out of her mouth.
We did not get to meet often from that night on. She did not want to meet when Cliff was at home, but when he was away we enjoyed several wonderful sessions. She was content with an hour or so in bed with me and refused to spend an entire night.
I did learn a little from her about her prior life. She had a lover before marrying and talked about the erotic pleasures they had enjoyed. The man she married had not been a pleasant husband. He had not abused her in any way, but had been alcoholic and their sex had been sporadic and not fulfilling at all. He had been killed in a work related accident following the birth of their last son.
Dorothy had raised the five boys all on her own. She had never taken another lover after her husband’s death but admitted that during the last year or so before my arrival she had began to think of sex once more. She thought perhaps that her interest in me as a younger man took her back to happier times before her marriage.
When the school year ended she told me that she would have a room available if I ever returned. I did return that summer to be best man at Cliff’s wedding. His liaison with his girl friend had been more productive than mine. In fact his new wife had a bit of a bump in her bridal dress at the wedding.
I did call Mrs. Chalmers to tell her that I was coming to town, but she told me that she had a summer boarder and did not have a room for me. I was to learn a few years later that the summer boarder had asked her to marry him, and she had accepted. I like to think that my times with her in bed had refueled her desire to continue living a full life. The memories of those times continue to provide me with nothing but pleasure.