Fooling around with a friend's mom the summer after high school

I haven't written in awhile, but I commented on a thread in another sub the other day about titty fucking and it reminded me of something that happened right before I started college.

I'll probably get judged here, but fuck it.

Names changed for anonymity. I was 18 when this happened.

In high school I had a large close friends group, 6 of us guys. We all considered each other best friends. We graduated in May and were gearing up for college. We always hung out at each other's place. This occasion was no different.

Mid-July. We all planned to show up at Josh's house around 2, but somehow I got the time confused and I got there around 12. Only Josh's mom (Sandy) was there. She told me Josh didn't get off work until 1:30 so he wouldn't be back until just before 2.

Sandy was about 40-42, blonde and was divorced. I had always lusted after this woman. She was around 5'8" or so, probably 145-150 pounds, with breasts that you only saw in magazines. I loved when we all went to Josh's house for this reason alone.

She told me I was welcome to stay until everyone got there so I just said that was good with me. She figured I would game or something.

When I say game, I'm referring to original Nintendo. Between all of us guys, we had around 80 games and that's what the plan was this weekend.

I didn't want to start gaming yet, I wanted to be around her. She was wearing shorts and a tank. Her hair was wet so I'm guessing she had just showered. She always wore a bra because her breasts were so large. If I had to guess their size, I would say they were likely E or F cup. They were insanely large, the largest I had ever seen at that point in life.

We were in the den of the house moving stuff around like she was looking for something. I was standing about 10-12 feet away, just chatting her up and watching her, probably creepily. She knew it, but didn't say anything. Honestly I was flirting, but didn't really know how to flirt with an older woman. She just occasionally smiled at me. We were bantering back and forth and she reached up to an upper bookshelf to grab a box or a basket (I don't remember exactly) of stuff and it slipped from her grip. I lunged forward to help catch it, but I came up behind her, reaching above her. The box continued to slip down and in my attempt to stop it from falling completely I ended up with a large handful of her boobs.

I was likely already sporting a tent in my basketball shorts, but I definitely was after that and it was obvious. She felt it on her backside when this happened and we just kind of froze. The box had fallen, but we weren't paying attention to it anymore.

After a few seconds I removed my hands and stepped back, apologizing repeatedly. She grabbed my hands as if to calm me, saying it was ok. I was honestly kind of freaking out over it, almost in a panic. It definitely wasn't the first time I had my hands on boobs, but I had only touched girls my age before.

We stood there in silence for a second and then she asked if I had never touched someone before. I didn't directly answer, just saying I was sorry again.

Then she surprised me. She said it was ok, she liked it.

"Huh?" I thought to myself. Then she took my hands and placed them back on her breasts. I just stood there, frozen, not knowing what to do. Part of me wanted to leave, the other part wanted more.

"It's been awhile. Touch them."

I still just stood somewhat frozen, hands not moving.

Then she told me to relax, it was ok. She guided my hands as if to caress them. She reminded me that while this seemed awkward, we were both adults. I relaxed a bit at that point and allowed my hands to begin clumsily rubbing her breasts, circling my thumbs where I imagined her nipples were. She just closed her eyes, I thought she was enjoying it.

Then she said something like "I'm going to teach you something because your grip is off."

She stepped back, removed her tank top and unsnapped her bra, letting them free. I know I looked stupid just staring at her breasts and eventually I brought my gaze up to look her in the eyes. She grabbed my hand and pulled me while she walked towards her bedroom. Closing the door behind us, she said "we have a little time, sit on the bed"

I followed her instructions, sitting kind of in the middle of the bed, on the side. She positioned herself as to sit in my lap, but had me scoot back to where she sat directly on front of me. She grabbed my hands again, wrapping them around her and placing them back on her breasts.

Let me tell you, my heart was thumping!

She told me she was going to teach me about foreplay. She then sat out to teach me that sexual play wasn't about getting the nut, it was about pleasing a woman. She guided me through nipple play while asking me to kiss her softly on her neck up to her earlobes.

After awhile of this, she told me we weren't going to have sex, but she was willing to play around. I was good with that, blue balls be damned.

I continued caressing her breasts, kissing her neck and shoulders, and occasionally nibbling on her earlobes. I was enjoying it and she was enjoying it. Eventually I pushed a hand down into the wasteband of her shorts. She reminded me again that no sex would happen, but we could play. I again agreed.

I'll be honest - at this point in life I didn't know about the clit. I thought manual stimulation of a woman was to put a finger or two in and move them around. Boy was I wrong. After my fingering attempt, she stood up and removed her shorts, now completely naked. I was in complete awe at the sight before me. She told me to undress and lie in the middle. I stood up and awkwardly removed my clothes, almost shielding my nudity.

She giggled. She actually giggled.

I got over it and sat on the bed. She crawled up next to me and grabbed my hand, placing it back between her legs. Her pubic hair was trimmed and thin, the style at the time. She talked me through finding and focusing on the clit, while not ignoring the rest of her pussy. I worked my fingers through her folds, and again she grabbed my hand as if to point my fingertips directly to her clit. She said something as if she was introducing me to someone when my fingertips stimulated her clit.

She placed her hand on my cock and slowly started stroking me. By this time I was leaking precum like crazy and felt like I was about to explode. Using her thumb, she was smearing precum all over my head. God it felt good, but she had to remind me that this wasn't about me, it was about us. I refocused playing with her clit, occasionally sliding fingers inside of her. By this time she was outright enjoying it, starting to squirm around atop the bed. I repositioned a bit to start sucking on her nipples, while still playing with her pussy. She was really getting into it. We kept this going until she had an orgasm. I'll never forget watching her body react to that. That was the first obvious female orgasm I had witnessed and I wanted to give her more.

She stopped to check the time, commenting that we were good for about 30 more minutes. Then she got up on her knees, angled to the side of me, and started to lick my shaft and head. She never fully took me into her mouth but it didn't matter, I was going to cum pretty quickly.

A few minutes in, I'm playing with her breasts while she's playing with me and I told her I was going to cum, and she just stopped. Her hand was still gripping my cock, and then she said she had an idea. She had me sit on the edge of the bed and she got on her knees next to the bed, right in front of me. I thought she was going to give me head at this point but no, she placed my cock between her breasts and started stroking me with them. Timing it with her thrusts, she would bob my head barely into her mouth, barely getting her lips around it. I didn't last two minutes and I exploded all over her chest. That was the most cum I had ever seen and the first experience cumming with a woman, without a condom. She milked every drop out she could get and then wiped herself off.

Then she asked me something I didn't expect: had I ever given anyone oral?

I didn't lie, telling her I had gone down on one girl but I don't think she enjoyed it much. I thought to myself that it seemed more mechanical than sexual. She then laid down on the bed and told me to do it to her, but to remember to focus on the clit.

It suddenly all made sense why my other partner didn't seen to enjoy it. I didn't know about the clit before.

As my tongue touched her, she said to include all of her pussy, but the real focus would be the clit. Keeping that in mind, I slowly started licking her lips lightly, stroking her labia with my tongue, up and down her entire pussy. I didn't forget the clit and she bucked her hips a bit the first time i glided my tongue across it. I quickly understood what to do.

I focused on her clit for 20-30 seconds at a time, then drifted down her pussy. I even grazed her ass hole a couple of times and she seemed to really enjoy that, although it wasn't intentional on my part. By this time, I'm hard again but I'm completely focusing on pleasing her. At some point when I'm licking her clit, she grabbed my head and held me in place, grinding her pussy against my face. She quickly came again.

I absolutely loved it when she grabbed my head.

I licked her clean and stood up. Her hands were covering her face and when she looked up at me, she saw I was hard again. She told be to come closer to her. As I did, she grabbed my cock and started stroking it like it was her job. I'm no time, I felt my balls tighten up and as I was feeling that euphoria of a building orgasm, I told her I was about to cum again. At exactly the right moment, she leaned back but kept her arm extended, hand on my cock. She jerked me off like that and I shot cum all over her.

All over her.

She quickly got up, started grabbing clothes and told me to get dressed because Josh was on his way home.

I hastily cleaned up with a washrag while she jumped in the shower. When Josh showed up, she was still in the shower and I was popping in a game.

This wasn't our last encounter. I'll tell another story about that one later.

This encounter introduced me to a couple of kinks I developed: older women and eating pussy.