Here I am sitting on a plane heading to Chicago and then connecting to a commuter to Iowa. Why, I heading to see a friend (and occasional lover) for 2 nights. I’m not sure even if we are going to do anything so much has happened in the 4 years since we last saw each other. I do have a marriage and 3 grown kids so again, what am I doing….
A bit of explanation is in order… Linda and I met over 40 years ago while she was a Senior in High School and I was just starting College with her then boyfriend Ken. We never even thought of each other as dating material, we were more a brother/sister to each other. You see, my biological sister and I aren’t close (I haven’t seen her in over a decade) and Linda is an only child. She went on to marry Ken (I was in their wedding) and after a few years of his working as a tech. and going to school Ken got his degree and moved to Iowa to pursue his career. I met and married my wife before they moved (and I graduated) and we were friends with occasional evenings out for pizza.
After we both had several kids we kept talking about our lives by phone (remember, this was pre-Internet days) and she mentioned she was coming back to town to see relatives. One thing led to another and we ended up meeting in Indiana before I rode back with her to Ohio. Even though we didn’t decide in advance to jump in bed together, it did happen. I was her 2nd man ever.
Linda was a virgin when she married due to some medical issues concerning how small her vaginal opening was so she hadn’t slept with any other man. I was safe (already having been “fixed”) and my number of partners could still be counted on the fingers of 1 hand. We were experimenting as much as having a deep relationship and the night was glorious.
Well, living a time zone away restricted our meetings to once every few years so most of the time we still served as a brother and sister as our life unfolded (You know the times when you needed to vent about your spouse, we were the pressure relief valve for each other). I eventually moved to Arizona for work and to be near my parents so it was even further distance and I relegated our “visits” to the past. That stayed that way for many years…
Then about 4 years ago I had a business trip over to Atlanta and I could route myself thru Chicago and spend a day or two there. I mentioned it to Linda and she thought she could take a day or two there as well. We did that and spent about 36 hours exploring each other’s bodies for what I suspected would be our the last time. After all I was retiring in a year or two and would not be typically travelling alone. A 60 year old that came 4 times and thought “what a way to have our last fling”.
Well the best laid plans didn’t work out and 5 years later I’m still working and Linda divorced Ken. We don’t need to go into details about the divorce other than to confirm that I was not part of that split. Now up to today…
I have a business trip again and extended it by 2 days. Using frequent flyer miles, I routed myself through Iowa. Linda and I had only seen each other at her younger son’s wedding 2 years ago and of course we were on our best behavior. I really didn’t know if we would still have a spark and honestly I wasn’t sure if she had reached a point where men in her bed were going to be part of her life anymore. Linda did try a relationship after being single but it didn’t work out due to health issues and she is both disappointed and independent now.
Well I texted her when I landed at ORD and confirmed my arrival in Iowa about 2 hours later. There were no delays and I arrived, waited for my bag and then sent her another note that I was heading to the curb. Well, about 2 minutes later she drove up, got out and we hugged, throwing my bag in the back and climbed in. Some small talk kept us going until we got to her condo.
The two of us went up the steps from the garage into her hallway and to the kitchen. I dropped my bag in a corner and she started the “tour” of her place. It wasn’t too big but quite comfortable for what she needed. Upstairs were the bedrooms where she had a job for me; to install a light kit on a fan she had put up a few weeks before. Before I saw that I was shown her bedroom with a king size bed and the bath on the other side of the room. We started over to see the bath and Linda turned around and kissed me. It wasn’t a “welcome to my home” type; more like a “I need a someone now” with tongue and sucking. It lasted almost a minute and I had a reaction as you might expect. My hands wandered down to her butt and fondled her cheeks while her hand moved to brush my crotch. I had to move my hand up as well to her boobs and softly hold them.
This reminded me of a “Big Bang Theory” episode at the end of Season 5. It’s the one where both Lenard and Penny were thinking about dating and separately were introduced (or reminded of) Schroeder’s Cat. Briefly, this example is to explain to Penny that until they try out the relationship, there is no way to know if it will be good or bad, alive, or dead. On the episode, the 2 of them kissed and Penny said “Alright, the cat’s alive, let’s go… ”. That felt the same way this time for us.
We eventually broke apart as she really did show me the rest of her place. I figured the spare bedroom would remain spare for us and we ended up back in her room. Another kiss next to her bed and our hands were all over each other. I slipped my hands under her top and fondled her breasts and lifted the bra up so they were directly in my hands. Linda had really firm breasts; they still seem to be asset of a 15 year old. She wears a bra for modesty, not support. They are about 34 C so I can easily get most of them in my mouth which I wanted very badly. She was busy too getting her hand between my legs and rubbing my erection to full size.
This led to me pulling her top off and her getting my last buttons undone, sliding my shirt off. I for a moment just hugged her feeling her firm breasts pushing into my chest. She kept at it undoing my belt and sliding my zipper down to get better access to my equipment. The pants fell and I did the same on her so we were standing with only a bit of under wear and shoes still on. She reached over to the bed and pulled the covers down, plopping the 2 of us on the sheets. We pulled off the shoes and shorts and we both had nothing but a smile on. Her mouth was all over mine sucking both lips and tongue which is something that I had never seen in her before. In our past, she was a tender kisser, and love making was quite conservative, missionary style. Now I had a wild woman all over me which I loved.
I eventually worked my way down to her breasts and started sucking. I remember they were sensitive so I didn’t bite or suck too hard but even then she wanted me to go easy on them. I headed back up to kiss some more and my hand wandered between her legs. I lightly rubbed her clitoris and even deeper inside and she started growling, at least that is the only word I can come up with. It seemed a turn-on so I kept doing that and she keep encouraging me on.
And of course she had her hands on by dick keeping it hard. After several minutes she broke free a bit and said I have a magic cream to use and got up on her dresser and came back with a cream that was so slippery on her hands over my most sensitive parts. So between my fingers and hers, we were so wet and hard it was difficult to keep from jumping her bones right then. I held out and was in another world while I kept keeping that growl coming from her as well. After what was probably too short a time she moved around and it was obvious she wanted my hard member inside. I moved over her and it slipped in so easily even though she is still tight, and that is with 2 births under her belt. Every part of me was being squeezed as I moved in and out. 10 strokes, then 20 and 30, I already was ready to burst. No matter how I tried to extend my endurance the cream and her glove like body did its thing and I felt the fluids building up inside. Once I hit that point it’s no stopping my body in its job, to do what it can to impregnate the woman I’m inside no matter what we have done to prevent that (and that doesn’t include our age). One spurt, then another, I was fucking Linda with no holding back. After 4 years she was sharing her body and we both loved it.
After a way too short a time I slipped out of her. Guess the ol’ dick doesn’t stay hard as long after cumming as before. We snuggled for a bit and by then it was almost dinner time. She had a steak place where she wanted to go so I took a shower while she “cleaned up” as Linda put it since her mess was “inside”. I was hungry so the steak tasted great and to top it off she paid. Guess women’s lib got all the way up the age range. Knowing that a part of me was still inside her kept my sexual interest and I had a bit of a hard dick throughout.
We headed back to her condo and once settled in started making out on her couch. I had my hand up under her top again and she was massaging my crotch while having a session sucking on each other’s mouth. Ten, maybe fifteen minutes passed and she suggested we head upstairs. Well my dick was already pushing against my pants so it would feel much better to release it. Actually I was a bit surprised it was so hard again, in the last several years I’ve only cum once in a night. We got to her room and had a bit more orderly disrobing as we watch each other slide off everything and met under the covers. She had already gotten that “magic cream” out and her hand headed right for my most sensitive spots while I moved in on her boobs.
We were already turned on so it came as a surprise when she said “I’ve learned a few things since last time I saw you” and proceeded to start sucking my dick. She had been very conservative in sex in the past so that had never happened before. Her tongue was quite skilled even if she had not that much practice and I just laid there with nothing in the world mattering except the spot between my legs. After several minutes she came up and asked if I liked that. I could only nod in approval as my senses were still recovering. Once I could get active I tried to reciprocate by nudging down to her waist but she held me up from doing that. I guess somethings are still a bit too far out for her to accept.
After several more minutes I went to enter her again but I wasn’t quite hard enough so we kept up with the foreplay until I was solid again and pumped into her again. It took a while longer and she came at least twice before I shot my load. That totally spent anything I had and I think she was as well as we fell asleep in each other’s arms in just a few minutes.
Morning came and we still were spent so after some showers we headed out for breakfast and parts for her fan. That afternoon I did several of those odd jobs a “guy” does around the house and we had an early dinner before she headed out for a couple hours to be with her grandkids.
When she returned I had recovered from our “activities” of the past night and we shared some time on her coach once more. Once she had me hard again we did head upstairs again and got naked. This time she had some ideas that included making me so completely satisfied that I’d have nothing left in me. I did finger her to that growl again several times as her hands did their task. Once she seemed to have cum several times (not so explosive an orgasm but more a continuing pleasant stretched out contractions) she sat up and got both of her hands working on my dick.
It was already hard and I had every intention on entering her but she just seemed to continue to rub and massage my balls. I kept getting closer and closer and I even said I want to be inside you soon but Linda kept working on me. I got really close and gave one last try to jump on top but she didn’t allow that. I started tightening muscles and knew I had lost that battle. That relaxed me and I laid back to enjoy her hands. A few seconds later I started pumping all I had into her hands. My crown got sooooo sensitive and I tried to move her off but by then she was on top and held me in place. My whole world narrowed down to that little spot that felt both pain and pleasure, I didn’t care about anything else.
Eventually I stopped squirting and slowly came down. Thinking back, I hadn’t had a hand job for many years and that she was able to do such meant she learned a lot since I last knew her body. She wanted to snuggle and I was happy to oblige drifting off to sleep complete drained and contented.
My last morning I had nothing left. We stayed in bed for a while and then cleaned up before heading to the airport. I had not expected to cum 3 times in just over 24 hours; after all I’m 66 and nothing like I was at 20.
We’ve kept in touch and are hoping to have another Chicago encounter this summer when I’m back east. I’ll be 67 by then so we’ll see if I can still behave as I did last fall. Well, off to the Fitness center to try to do just that. I’ve been told that if you are still fit, you can keep going into your 70s and maybe even 80+. At least I’m going to try.