She wanted me to watch [MF]

We had spent the night together, Lynda and I, and had been extremely energetic before falling asleep in each others arms.

The next morning, we woke up slowly, but once awake, had our way with each other a couple more times, until we were completely awake and completely energized.

By the time, I was completely spent, every part of me. While at this age (50+) it wasn’t unusual to have completely worn out my cock, I had never had the experience where I couldn’t keep cunnilinging until my partner was spent.

But this time I was. My cock was worn out, my jaw was sore, my tongue was tired. Even my arms were tingling, from holding myself above her as well as some vigorous manipulation.

But Lynda still had another round left in her.

She sat me down, completely naked, in a chair at her kitchenette, and walked around in a short fuzzy sweater and a thong, getting us coffee. The sweater covered most of her ass, I could see it tickle her as she moved. And when she reached for something, the bright red strip running down between her cheeks peeked out.

She wanted to write her name in the snow [MF]

We had gone hiking after a fresh snow. There were several trails out in the forest preserve we were exploring, some are pretty deserted in the winter, particularly the side trails, and there are a lot of hills, so it makes for challenging hiking once it starts snowing. We didn’t have snowshoes, but due to the fresh snow, we figured it wouldn’t be too icy. And it wasn’t too cold, that sweet spot just cold enough to snow but not enough to be frigid. And fortunately, sunny and no wind. Beautiful day.

So we’re hiking and every once in a while stop to make out and play a little grab ass. The weather meant she was was wearing tights and yoga pants over them, and several layers of thin but warm sweaters, I was wearing jeans and similar layering on top. Thanks to modern day technology, we were both plenty warm without any of the bulky gear from years ago. And both in hiking boots, it’s warm enough to be a little slushy and messy, gym shoes definitely wouldn’t have worked.

Why haven’t you kissed me? She asked. [MF]

This is what she asked me after the baseball game this weekend.

Lisa and I met years ago, having been set up on a semi-blind date by two groups of friends who knew each other. We were given each other’s pictures and the elevator pitch, and agreed to meet for dinner. There was definitely some sexual chemistry, dinner couldn’t get over fast enough so that we could go for a walk and make out.

We became quite interested in each other, she sent me a number of becoming pictures of her, including several in a bikini, she looked GOOD! We arranged a second date as soon as we could.

Unfortunately, our second date went much worse, as she was hungry for a lifetime mate while I wasn’t completely positive about how to spell her last name yet. She grilled me on religion, politics, kids, retirement, and we discovered that we were pretty far apart on many of these subjects. I walked her to her car, we kissed a few times, passionately but wistfully, and that was that.

She [F] gave me a peek, I [M] gave her more

Driving to see a customer today, I passed through a small town where long ago I met a woman, Kris, for a first meeting that turned out way different than either of us expected. Oh, the memories!

We met a a small lunch place in the outskirts of of a one-horse town, truly, there wasn’t even a stop light on the highway. We lived over an hour apart, this small town was the only convenient place anywhere in between, 20 minutes for her, 45 for me.

She was a big city girl who had grown tired of the fast paced Madison Avenue, party-all-night lifestyle, and having socked away a sizable nest egg, had bought a farm and taken a job as an administrative assistant in the local high school to keep her busy as she came up to speed on her new property.

It turned out her past life was harder to shuck than she realized, after a few months, she was going stir crazy, and agreed to meet up with me for a sandwich just to get out of her self-imposed solitude.

For the first time in 8 years, she wanted me to… [MF]

I met Toni about 8 years ago on the sadly-defunct Craigslist personals. We were that perfect match of enjoying each other’s company, making each other laugh, and perpetually horny. Her husband was one step short of a rapist, treating her like property, and while she plotted her escape, she took solace in my company, and I let her take charge, controlling our interactions, an experience she never had with him.

Myself, it was a fantastic time, we flirted and joked regularly, I teased her, the long, drawn-out foreplay, and when she was ready (and available), she’d call and we’d get together for lunch and some fooling around.

Because of her unpleasant experiences with her husband, she wasn’t that interested in intercourse. Instead, she wanted oral, a lot of oral. She would often come over to my house, or visit me at my office, when nobody was around, and after a few few minutes of talking, she would start to get handsy, running her fingers over my chest or my thighs, getting me more and more worked up. Not that she really had to work that hard, whenever she asked if I was free to meet, I’d start to get excited, and was often ready to go by the time she arrived.

She didn’t expect that I would notice she wasn’t wearing a bra [MF]

Years ago, due to an interruption in child care, I was working at home one week over the summer. I had arranged a playdate for my youngest son, his brand new best friend was coming over for the day.

I was trying to get some stuff done before he got dropped off, together with a neighbor’s kid, there would be bedlam for the rest of the day. Suddenly I heard a knock at the door, a glance at the clock told me that they were a half hour early. I had just thrown on a pair of grey nylon athletic shorts after my morning workout shower, not really presentable. Still I figured I could get away with it just to answer the door. I threw on a baggy tshirt and ran to the front of the house.

Opening the door, I find Matt and his mom, Kate, arguing with each other about how long she’d allow him to stay. “But Mom! I brought all my stuff.” he whined, showing her how stuffed his backpack was. “And Jack (my son) has cool stuff too!” She looks at me through the screen door and silently laughs out of his eyesight. He flings the door open and she grabs his hand. “Give me a kiss goodbye!”

She was disappointed I didn’t wear my work boots [MF]

Joan and I began bantering immediately after meeting on ‘one of those apps’. Unlike most women whose repeated half sentence answers indicated a desire to either play hard to get or simply a lack of interest, she was easy to talk to and was fully involved from the start. Her first message was long and to the point, I responded in kind, and within a day, we were both interested in meeting.

Within another day, she suggested a phone call, again, being direct and to the point. She wasn’t wasting any energy in determining if I was worth her time. I suggested we meet up that night, as she was on the road and I knew she would be available that night. She agreed, with the warning that her time was a little up in the air. We settled on a place, and the waiting until 6 pm began.

I was at the office, the usual ‘business casual’, but not really right for a first meet, I would have preferred to have upped it just a notch. So in order to set expectations right, I would have hated for her to have gotten dressed up and find me in sneakers, I teased her about the dress code for our first date.

[M]y girl[f]riend’s sister – the sequel – surprising her with a “footrub”

A lot of readers asked if there was a followup to the tub handjob encounter. Eventually there was, but it took a while to happen.

I’d been checking her out and fantasizing about her since I met, so to have something actually happen was beyond my wildest dreams. On the other hand, I was very serious about my girlfriend, and there was no way I was going to mess that up by screwing around with her sister. I rationalized by telling myself I was sick. And her sister was very serious about her boyfriend, they’d been together for something like 6 or 7 years at that point, and they had made it clear that they intended on getting married. So both of us were in it for the long haul.

Nonetheless, there was undeniable chemistry and interest, and so every time we saw each other, sparks flew. She was naturally flirty with everyone, so her friendliness with me didn’t send off any warning signals, but at the same time, I had to keep her at bay lest a repeat occurred. We were lucky that we didn’t get caught that time, it just wasn’t worth it to take a chance again.

[M]y girl[f]riend’s sister surprised me

A recent GW story reminded me of something similar that happened to me post college.

Was staying at my girlfriend’s house after college. I had gotten sick, so while she was at work, I slept in. Still burning up with a fever, I tried taking a bath. The only other person in the house was her sister, Brenda, who was in her first year of college. She’d always had a thing for me, since early high school, despite having the same boyfriend since 6th grade. Would always make little comments like ‘hey sexy’, would rub up against me, her hugs would last a little longer than needed, that sort of thing.

So I was in the tub trying to cool down, and she knocked on the door. “I have to pee!” she calls through the door. The problem was that the house was perpetually in repair, and this was the only working bathroom in the house, on top of that, there wasn’t even a shower curtain, hence the bath instead of a shower. I tell her I’m in the tub, and she promises she wouldn’t look, if I promised her the same. I tell her that I covered myself up and she can come in. I reach for a hand towel and cover my midsection, then closed my eyes and told her to come in, but to hurry.

[M]y [F]irst One Night Stand Went Bad, then Sideways, then Much Worse

This was years ago, I was just entering the scene after a long monogamous stretch. I was talking to this chick online. She only provided one picture, looked like a Linked-In head and shoulders shot. She was very attractive, in a ‘handsome’ sort of way, with long, straight blonde hair. She’d told me she was taller than most guys, so I assumed between 5’8 and 5’10, and from her picture, I could tell she was solidly built. (Not fat, just big shoulders, big hips, muscular arms.)

She was very aggressive in text, constantly telling me how good looking she was, that when she went to the gym all the guys stared at her, that she knew everyone wanted her and she could have her pick of guys anytime she wanted to. It felt like she was trying to convince herself of that, but I didn’t know enough about her to tell what her backstory was, perhaps she had been in a relationship where he had abused her mentally, insulting and talking her down.