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My first time was with the daughter The second was with her mom Part 1

I first met Helen, the mom, when she asked for help finding something in the grocery store where I worked, part time. I helped her find what she needed, and as we walked through the market, she struck up a chat. 5'8", mid 40s, business suit with skirt and heels, and smelled amazing. At the time, I had no idea what a MILF was (heck, growing up in a conservative/Christian household, I didn't know what basically anything was!), but objectively speaking, Helen was a very attractive woman. And for as long as I can remember, I've always liked the skirt/dress and heels combo. She thanked me for my help, and said that I was a "very nice and helpful young man". How sexy?! HA!

A few weeks later, I was stocking some shelves, and Helen called out to me from up the aisle. Alongside her was a very attractive young woman -- tall, like 5'10, and with a fantastic body / very well dressed, that she introduced me to as... her daughter, Melissa. What an absolute cutie, oh, and Melissa was going to start working at the supermarket, too! She was super friendly and funny, and while undoubtedly I fumbled while I flirted, she'd pat me on the arm and laugh at my corny remarks.

You might be wondering how this story fits into an adult / swing site, and I'll somewhat ruin the punchline here. Being with Melissa (read on), and later with her mom (next story), made me acutely aware of the fact that I'm a highly sexual person, and, regardless of my conservative upbringing, that there is no reason to be ashamed of it. Having these foundational relationships helped me immeasurably as I found myself gravitating towards ENM, group sex, and same-sex activities. It was incredibly liberating.

We were having an unusually hot spring that year. It was high 90s in May, and humid. Even though I hated working at the market, they kept the place like an icebox, which was a welcome change from my parents' house, where it was bound to be 90 degrees inside without A/C. My parents just happened to go on vacation that Friday, and would be enjoying air conditioning someplace thousands of miles away. This seems like a bad 1980s movie, and I guess that it kinda is. But unlike Judge Reinhold ogling Phoebe Cates in "Fast Times", there would be a pool involved, but there would also be physical contact. Ah, another spoiler.

I ended my shift at 8pm, just when it was getting dark, and my driver's license at the time allowed me to drive until 11pm. As I usually did when I took my breaks at the market, I popped my wallet and car keys (if my parents let me drive on that day) on the break room table. As luck would have it, Melissa turned up in the break room at the same time (okay, it was planned; she told me later that she begged to get an earlier break). Her hair was pulled back in a ponytail, another look that I really like on a woman, and she was wearing this blouse (extra button unbuttoned), stirrup pants, and 2" wedge heels that were popular in the late 1980s. She sat as close to me as possible, and kept touching my thigh or touching my arm, or just making intense eye contact without saying anything. Then she asked if I had a car with me. I explained that my parents were out of town, so that I would have to drive myself. The short of this story is that I got called into the manager's office at 8pm, right as I was clocking out, and they asked if I could drive Melissa home as she was "not well", and also because she said that both her mom and she knew me. Which was true. Somewhat.

I drove Melissa back to her house, not knowing that the whole thing was a ruse (I was such a rube back then), then she invited me in, and offered me a beer. I didn't drink, but wanted to seem cool. She said that her mom was "super cool" and more like a sister, in particular after the nasty divorce that her mom went through, and said that she could have some beers -- so long as she didn't drive / get "sloppy" after having a few. So I took a couple of swigs, and it went to my head (or both of them) immediately. She gave me a tour of the house, which was impressive, and made a few off-hand mentions of how her mom got the house in the divorce, but that as a nursing supervisor during the day, her mom wouldn't be back until 2am or so -- because she would bartend on Friday and Saturday nights -- to keep up with the bills.

Then she showed me the in-ground pool in the backyard, and asked if I wanted to take a swim. I told her that I didn't have a suit (god, this is so much like a bad 1980s movie!), and she said that when she was home alone, and it was dark out, that she would just strip down and take dip in the pool. She reached for a light switch inside of the sliding glass door, and all of the lights went out. In the faint moonlight, I could see her stripping. But I only made out faint shadows of her shapely, naked body. Then I saw her dive into the pool, and heard the splash. I stripped as quickly as I could, and hopped into the pool. I have to admit that the tepid water felt amazing against my naked flesh. I felt somewhat embarrassed that I was sporting a huge hard on. Melissa, and women like her, do that stuff to me, and I say that as someone who is in his 50s now.

She was on me right away, even as my hard on poked against her thigh. She basically stuck her tongue down my throat and wrapped her long legs around me (I'm a really tall guy, and I admit that having her do this was super sexy). We kissed and fondled and pinched and my cock nearly entered her twice, for about 15 minutes in total for all of this, should I guess. Then she grabbed me by the hand and led me back towards the house. She grabbed a couple of towels, and we tried not to get a ton of water inside. She started toweling me off, including playing with my nipples a lot with the towel (I had no idea it would be this arousing) and definitely tugging at my cock. I took various liberties as I toweled her off as well, but lesson learned when she told me that aggressively toweling her pussy "kind of hurt, so I should stop".

She grabbed my hand again, and pulled me inside the house. She laid two towels down and told me to stand on one of them. Again, I felt kind of embarrassed that my cock was at full mast, kind of bobbing around like a flagpole in a windstorm. She bunched up her towel, then got on her knees. Quickly, she popped my cock into her mouth and started pistoning my cock into and out of her mouth. She told me to enjoy it, because "all guys like this shit". Then I started face fucking her, and she stopped the action, and told me that I was being rude. Then she asked me if it was my first time, and I told her that it was. She expressed how excited it was for her to share herself with me. That's verbatim. She stopped kneeling on the towel, and moved to a squat. Her labia were sagging and pronounced. I had never seen anything like this in real life before, and it was blowing my mind. Hell, I hadn't seen anything to that point. She snaked her fingers between her legs, telling me how much she wanted us to have a good time that night, then her finger disappeared into her pussy. She stopped touching me entirely, and then her whole body ceased up; a bunch of liquid came out of her pussy and it soaked the towel. Then she put me back into her mouth. She guided my own pump action, and I didn't last long. I told her that I was ready, and she thrust my hips toward her jaw. Then I unleashed rope after rope down her throat. I thought that my own self pleasure, by way of masturbation, was exciting. No. I was wrong. Her silky smooth mouth milked the cum out of me tout suite.

When I was done cumming, she got up, and kissed me on the mouth. Yes, during self pleasure, I had tasted my own cum before. But I tasted her girl cum and my own cum on her lips, and instantly I got hard again. She asked if I wanted to go up to her bedroom, and I nodded my head yes. We headed upstairs, and she laid down on the bed, spreading her legs. She motioned with her index finger for me to get between her legs. Then she stuck her middle finger in my mouth, and motioned with her index finger of how she wanted me to lick her pussy. (Full disclosure: I'm not an unpleasant looking guy, but I'm also super nerdy. I cannot believe that this, among other things, happened in my own lifetime.)

I went down on her, my first time tasting pussy. I expected a full bush, but no, all of her hairs were very short. As I followed her instructions, she told me how she didn't like a lot of pubic hair, which was the norm in porn those days, and that maybe we could shave each other at some point. I just kept licking and tonguing. It was the first pussy that I ever tasted, and it was fabulous. Finally, and I thought that she was having a seizure, her body started convulsing. Then she forced my face away from her pussy. She sat up and pulled me down on top of her. She grabbed my cock and guided me right into her hot and wet pussy. Oh. My. God. Think of silk and velvet, and of the best thing to ever touch your penis head. It felt soooooo good!

I started pumping, but she started teaching me. She told me to put her legs above my shoulders, and told me the pace that she wanted. And the dirty talk resumed. Did I think that her mom was hot? Did I think that she'd be giving up her pussy to me on that night? Did I like fucking her? She told me that when I needed to finish that either I could do it outside, or I could do it inside (she said that she was on the pill). But if I did it inside, that I would have to clean up afterwards. I didn't know what that meant.

Now, and this is not a brag, I cum a LOT, even at 50. I can go multiple rounds, with each round being longer than the last. And for someone, a man and/or a woman who's into that, I am able to perform several times per night. The first time I came in Melissa, the convulsions started again. Then, once I started getting soft and plopped out, she told me to get between her legs again. And yes, I ate my own cum for the first time, well, at least out of a hot pussy like hers. Then she told me to get on my back, and ran her labia up and down my shaft until I got hard again. Then she put me into her cunt, and slow rode me, all the while telling me how much she liked getting her nipples pinched, her ass slapped, her hair pulled, etc. I kind of lost track of time at that point, but I came in her again, and cleaned her out again. Melissa told me that she was looking for a summer "romance" before she went off to college, and that she couldn't wait to see how the upcoming summer played out.

I could swear that as she rode me that someone was watching. Like I said, I'd lost track of time. I feel asleep in her bed, and woke up in the same bed in the morning, and yes, I was in a panic. I tried to sneak out of the house, but sure enough, Helen called my name, and I found myself, holding my hand over my bare penis, gathering my clothes that were piled up outside of the pool outside. I got dressed with my back to Helen (Melissa had gone to work that morning), then she insisted that I sit down at their kitchen table.

Helen basically gave me a green light to fuck Melissa all summer, surmising that she and Melissa were "more like sisters" than mother and daughter, in particular after the nasty divorce, but that if I got Melissa pregnant, that I would be on the hook for something that I might not want at that time. Helen said that ground rules were that I could come over at any time, but that Melissa's bedroom door remain open at all times.

So, what happened? I fucked Melissa all summer, and somehow Helen talked my parents into letting Helen and me driving Melissa to college in August. Between our first fuck and our drive to PA, Melissa would walk around the house all summer wearing nothing but panties or bikini bottoms -- and Helen, to my surprise, was completely fine with this. Melissa would even swim, topless, during the day, during those months, as Helen sat around the pool in her bikini.

Like I said, it was a summer "romance", and it was extremely welcomed from my end of things. But how I ended up fucking Helen is its own story. And I will tell that at another time.