Senior Therapy

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My First Grandmother.
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Who better to experience "therapy" with than someone in a similar situation, so it began when I met Carol. Back in those days the Internet was wide open, sites that advertised "personals" were mostly still "free"; the greed and exploitation for money had not quite started. Back in those days Yahoo Personals was such a site.

Carol had a lot of the same frustrations as I had back then, a libido that was far more active and in need of more than her man was giving. Yes, they would have sex but there was no foreplay and after a few minutes of grunting, bumping and grinding he blew his load, turned over and fell asleep, leaving her to take care of herself and very frustrated.

Our relationship began with emails which eventually got more and more erotic to the point that when I was out of town on business we would have strings of late night emails. I confessed early on to Carol that I was pleasuring myself while we emailed; she enjoyed my confession. After a few months of this we arranged to meet at a state park convenient for both of us; that is when I found out she had a young grandchild she was watching on her days off. Let me tell you about Carol. She is a smart and practical lady; she was several inches shorter than me, I am just short of six feet. I would describe her shape as fuller figured, not really quite a BBW; she filled out her jeans nicely which she wore most of the time; her bosom was more than ample and I would find out later that she had a couple of the thickest nipples I have ever enjoyed. Did I mention she had her own Harley that she road regularly? A motor cycle riding grandmother, OH MY! With her grandchild not of school age yet, that is how we arranged to meet up; she would come to the park for walks and we would have casual conversations while we walked around the lake; our conversations were mostly about our frustrations at home; it is how we dealt with our situations.

One hot mid summer day we arranged to meet up at a different state park, that would be our first meeting when she did not have her grandchild with; that is also the day when our relationship started to get physical. We got into the back seat of my company car where she discreetly exposed her breasts one at a time; I made sure she understood how much I appreciated the view. What I learned quickly about Carol, she was so frustrated physically and erotically at home that most any suggestion or slight hint I would make to her that involved her showing me her body and me showing myself to her, she would be more than willing to try at least once. She was more than willing to show me her breasts anytime she could do so discreetly. One afternoon, at a different local park, she was sitting on my lap, pretty much in plain sight of anyone in the area, she managed to uncover one of her breasts for me. She was getting very comfortable with the thought of baring a breast for me anytime and I was enjoying her efforts and made sure she knew that. She was also getting bolder and bolder and more daring about exposing her breasts.

We started meeting regularly after she got off work, especially when she knew her other half would be at work when we were meeting up. We also started going for rides in the country, using the back roads a lot; we would find a quiet place to park for a while to talk and enjoy each other's company. I don't remember exactly when and where it happened; we were probably having a conversation, maybe teasing each other some about wanting to see more of each other, maybe making suggestions via email as we still communicated that way a lot. Sitting across from one another at a picnic table one evening, she suggested I take a look under the table; I did; her thighs were spread; her jeans were unbuttoned; she was rubbing her hand on her panties and pulling them aside just enough so I could see some of her dark pussy hair. OH MY!!! What next? She excused herself and went to use the ladies room nearby; when she returned she said "Let's go" and we went to the parking lot. She got in my car, sat for a few moments before she opened her purse and pulled out her bra and panties, and smiled at me.

Looking around to see if anyone was watching, she let me see her nipples one at a time. She fixed herself up that way, then unzipped her jeans, wiggled a bit before pulling them down just enough so I could see her whole bush and pussy area for the first time. She let me look for a while, as long as no one came close to where we were parked; all the while she smiled at me. When she put herself back together she paused for a while then said, "It's your turn; I want to see you below." I slouched down some, unzipped my pants, managed to expose the head of my penis for her. Now I am not God's gift to women; certainly no adult video star; not even sure I am "average" size. I was nervous at that moment, exposing myself some for Carol in a semi public setting. It was my turn to make a suggestion. I whispered to her, "Go ahead, touch it if you want." She did more than just touch; she squeezed and massaged the head of my penis for the first time. I don't recall if I ejaculated then; if not, I am sure when I got home I pleasured myself to climax. Carol and I crossed the line that evening; our times together after would change forever. We started wanting a little more after that evening.

I recall going for a ride with her late one morning; we headed to a popular state fishing area; we parked in such a way that we could see anyone from blocks away approaching where we were parked. We were alone in the parking area, I turned to her and asked if I could see her below; Carol did not hesitate. She unzipped her jeans; wiggled them down to her knees; wiggled her panties down to her knees, then turned slightly and spread her thighs. A little while later she reached down with her hands to spread her labia apart; she let me have a nice long look. She made herself modest again, looked me in the eye and said, "It's your turn." I got my pants undone and my underwear below my knees, shifted slightly to face her and spread my thighs apart; I let her have a look for as long as she wanted. I was not embarrassed by my lack of size ever with Carol; she might have even done some touching and fondling that day?

The more we started discreetly exposing ourselves for each other, the more the topics for discussion in our emails got more and more personal; we shared thoughts and concerns about how far we wanted to take the physical part of our friendship. We both confessed to wanting more and doing more as older adults; we had crossed the line of exposing ourselves; it was then that we decided to start sharing the cost of a room for total privacy, and we did, anytime we could have at least four hours of what we referred to as "naptime". We would agree upon a location; I would make the arrangements; I would leave a note with the room number on my car; she would enter through a side entrance and make her way to our room. Once inside we would do whatever we were in the mood for that day.

What I especially liked about Carol; she had a very active libido; she was almost always willing to try new things especially in private. She was starved for physical pleasure at home; whatever didn't happen at home, she was free to express herself in private with me; and she did not disappoint!!! She liked being sensual and sexual; it wasn't about being nude, it was more about being dressed up just enough to be very desirable and more. She knew I enjoyed her breasts a lot so she would make her breasts that much more appealing; she went so far as to wear bras with open fronts that showed her nipples. She even got nipple clips to wear for naptime. The other thing she did was wear a thong; she did not have the body for a thong but it made her feel very sensual and sexual wearing a thong for me. I did not have the body for a man thong but I wore one just for her regularly. It was more enjoyable being barely modest in private and teasing and seducing one another then just getting nude right away.

Carol did whatever Carol wanted to do with me, to me, for me...in private, during naptime. Yes, we did try to get some actual naptime in. It was nice to wrap ourselves around each other's barely modest body, feel the warmth, experience the joy of being that close to each other.

One of the benefits of naptime, being in private together, we would regularly expose ourselves for one another. Carol would remove her thong, get comfortable, spread her labia and give me a long private show that left nothing to my imagination; she was completely exposed to the point that her clit was plainly visible as was the entrance to her vagina. More than a few times she would give me a long look into her vagina and at times the experience was such a turn on that I would have a spontaneous climax. In private Carol was more free than ever to do whatever she wanted which meant lots of touching and fondling and groping and molesting me, and I liked everything she did. She never had enough of playing with my penis and balls; I loved her touch. I was her private, personal man toy.

She got very comfortable pleasuring me especially with her fingers. She did everything in private with me that she did not do at home. I loved when she made me cum; it felt soooooo good ejaculating; she liked the feel of my fresh hot man seed on her fingers. There were occasions when she would make me climax early just so she could spread my cum on my package, then play more and make me have a second ejaculation. What I think both of us enjoyed about her wanting to make me climax a second time, it took a lot longer for that to happen so that meant she got to play with me longer and longer. The more she got to play with my penis and balls, the more she enjoyed it and more she wanted to make me cum. It got to the point that when we would go for just a drive, she would pleasure me with her hand regularly.

One time we went to a state park and went for a walk along one of its trails; it happened to be a weekday and the park was pretty much empty. We walked to the one overlook, she leaned against the railing over the spillway; I was behind her groping her bottom thru her jeans. At one point I got right up against her and started to dry hump her from behind; the more I humped, the more she pushed back against me. We continued down the trail, every now and then I would give her bottom a squeeze. Finally she stopped along the trail, turned to face me, put her hand inside my sweat pants and inside my boxers, and did not stop until I made a creamy mess all over her hand and in my boxers. I nearly collapsed when I climaxed; I had to put my hands on her shoulders to keep myself from falling to the ground because my knees got very weak from her having her way with me.

One time we went to an adult book/toy store to shop for a toy; we found a vibrator that was about my size, I bought it for her. Not long after we planned a naptime date and she brought the toy along. I had never played with a woman with a toy before. During our afternoon she got very comfortable on the bed, she got the toy out, turned it on and proceeded to put on a show, then invited me to use the toy on her. We had not had intercourse yet, yet in my mind we were doing the act except I was using a surrogate penis. In and out, in and out, in and out; at times I would leave it all the way inside her and when I would pull it out all the way I could look deep into her vagina, the toy stretched her vagina open that much.

There had been times Carol would suggest to me about wanting my penis in her mouth; I left that choice to her. It was a naptime date at a pretty nice place; I think the person checking us in knew what we were wanting the suite for??? We got very cozy in the suite to the point we were actually starting to nap. I had only boxers while Carol was barely covered below and completely bare from the waist up. Because I was so accustomed to Carol having her way with me, touching very privately and making me climax, I thought nothing when she tugged on my boxers and eventually removed them completely; I even had my eyes shut. I felt a new sensation, when I looked down I realized that Carol had my penis in her mouth. She was not giving me a blow job; instead she was taking her time nibbling on me like I was some delicious dessert.

She took her time giving me oral pleasure; I stroked and caressed her hair gently all the while I was I her mouth. The experience was more sensual that sexual. At one point I could feel a change in what she was doing; I was feeling more and more suction and her tongue was all over the head of my penis and once in a while I felt her tongue probe and explore the opening which was leaking precum. I let her know I could not hold on much longer; she simply continued doing what she had been doing until my penis throbbed and I erupted in her mouth. My eyes were wide open at that moment; I looked down at her, into her eyes, all she did was give me the sweetest smile when she let go of my penis. There was not a drop of cum on me, she had cleaned off every last drop and swallowed my entire load. I really enjoyed how Carol gave me oral pleasure, as noted earlier it was more sensual than sexual; I felt like my penis was a special dessert for her. She would be the first grandmother to give me that kind of oral pleasure but not the last.

We saw each other for several years; sometimes we just had lunch; sometimes she would bake cookies for me when I would go out of town on business; we made time for each other as much as our schedules allowed. As her grandchild got older it got more difficult to get the kind of time together we had gotten used to having, especially naptimes. We tried our best to set up a whole night together but could not get that arranged conveniently. One afternoon one nice early Spring day, we were at a state park close to where she lived; we had been in one of the park's shelters; I had been playing with her breasts, massaging her nipples and kissing each other. When we got back to the parking area, she was sitting next to me in my car, she had her hand in my lap, helping herself, something both of us had gotten very used to and both enjoyed. A truck drove past and she recognized it and the driver, it was her neighbor! We did not know if he had recognized her vehicle; we decided to cool things off a lot and it would be a long time before we would see each other in person, let alone enjoy the pleasures we had gotten so used to enjoying together.

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OneLongSchlongOneLongSchlong9 months ago

I’ve always loved fucking older married ladies. My first was 42 I was 18. She was the beginning of my addiction.

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