This story happened back in 2001 when I was still a bachelor / in the hunt and needed to buy a suit for a funeral.
TL;DR I decided to share this story after I just read a great story here about a guy who not only had sex with a married woman but also got her pregnant. I had a lengthy “relationship” with a married woman but did not get her pregnant. It was hot but ended strangely and abruptly.
The conversations you will read here are as I remember them.
I’ve always been a biggish guy. At some point my bachelor’s diet caught up with me and even though I worked out I was 6’6″/275 when I was 28 years old. When my mentor died suddenly in 2001, it was a shock. He’d touched the lives of so many, etc., and I won’t even get into that here. This story starts not because of my grief but because, simply, I needed something to wear and for a man of my size it’s always a challenge, in particular when I’m carrying more weight/bulk than I should be. This remains a problem even now that I’m post-middle age… and married.
I looked at the contents of my closet two days before his funeral. Jeans, t-shirts, and lots of cotton pants that no longer fit but I swore that I’d hold onto as “inspiration” for going on a diet and losing 80 pounds… someday. None of this was suitable for a funeral, and I asked the ladies at work for some advice. They said that I needed to buy a suit, preferably black, and that one of the chains of popular men’s stores was known to carry “larger” sizes (these ladies were beyond diplomatic).
I headed out to the men’s shop after work late Wednesday and a woman named Sheba (not her real name, but her real name was unusual enough that it accentuated her existing hotness) introduced herself to me, telling me that she was there to help me in any way she could. Sheba was a knockout, and I came to learn later that she was 38 years old, and married. Her curly, shoulder length strawberry blonde hair, thick but curvy figure, white silky blouse one size too small with that extra button undone, charcoal gray above-knee length skirt, black stockings/hosiery, and 4″ super pointy toed black stiletto heels screamed sex to me. She was friendly and charming, and if I’d have placed a bet on a sales person making a million bucks selling men’s attire at a chain store, it would have been on her. This woman just oozed sex. I was a late bloomer in terms of the birds and the bees and recently had started to hone his radar on women who gave this vibe of sexual confidence/openness. Unfortunately she was wearing a yellow gold wedding band. Still it didn’t deter me from flirting with her; she’d certainly been flirting with me, and it went beyond the realm of her trying to up-sell me on dress shirts, socks, ties, and shoes. I was sure of it.
Even though all of these men’s shops complain about men needing tailoring done at the last minute, they all do it. The tailor appears, grouses a little bit, then tells you that your alterations will be done the day before you need them to be. This time around Sheba took measurements of my oversized pants and jacket (it’s always a surprise when anything is oversized in my case); as she squatted at times to take my measurements I could clearly make out that she was wearing stockings instead of pantyhose. No lie, this thrilled me. A lot. Seeing her frilly stocking tops, and trying to look up as if I was staring into space was a real challenge.
Eventually she finished taking the measurements, the tailor took the suit for alterations, and after I’d paid for everything I left the store in hopes that things would be ready for the Saturday funeral. I got a call on Friday and headed to the store for a try on. Sadly Sheba wasn’t there, but things fit, and I would be set for the funeral on Saturday.
When I got home from work on Monday the light on my answering machine was blinking. Sheba had left a charming message thanking me for my business and her purring into the phone lead me to listen to the message at least once or twice more (yup, you know that I listened to it 50 to 100 times, reader!). I figured that was the end of our acquaintance. So I was surprised that when I picked up my phone on Wednesday night that Sheba, the most charming female sales associate on the planet, was on the other end.
Once again she asked me about my suit and reminded me that I needed to bring the pants (at least) in for a complimentary pressing. She gave me her hours for the week and asked me which of those would work for me. I told her that I was pretty busy and that not having the pants pressed was no big deal. That’s when the conversation took a turn for the interesting. She started asking me a lot of questions about me, and we laughed a lot. After about 15 minutes she moved the conversation as closely as she could back to business. Things had gotten a bit awkward, tense, or something. “So, is there anything else I can do for you?” she asked. As scripted of a question as this must have been — it took all of my might not to blurt out with “yes, you can absolutely put my fat cock in your mouth.” “Hello?” she asked. “You still there?”
“Hmm, is there anything I’ve left out here? Is there anything else you can do for me? Did I get that right, Sheba?”
“Umm, this conversation has gotten kind of odd, wouldn’t you say? I’m not saying that it’s bad, but I’m saying that it’s interesting to say the least.”
“There is something we’ve left out here, Sheba. It’s you joining me for a drink some night soon.”
There was silence on the line, and I almost said, “hello?” but I stayed quiet. “A drink?” she said. “Yeah, I can do that. When and where do you have in mind?”
I met up with Sheba at this local pub, and she looked hot. White (tight!) ribbed turtleneck sweater, knee length black skirt, tall black boots. When she saw me I stood up, and she came in for a hug. Sure enough she was wearing what looked like a wedding band. We chatted and laughed and at some point we got to talking about houses. She readily noted that she was married and that her husband traveled a lot for work. She also told me that they’d just had a brand new house built, and I feigned jealousy because, as I joked, I owned a shitty house that I prayed would burn down before I’d have it torn down. While our conversation drifted through several topics she kept laughing, touching my arm, at one point she gently touched my face with her palm, and without going into graphic details, well, or maybe *with* going into graphic details I sat there rock hard. On top of this all she smelled delicious, more than definitely good enough to eat.
Finally she looked at her watch and said that she had to go. I tried to not make a face that showed my disappointment. “Well,” she continued, “if you need ideas for your next house, you’re welcome to check out ours’.”
“I’d like that, sure,” I said. “I’ll just ring you at work, and we can…”
“No, I meant now, silly,” she said, slapping my arm. “Why not follow me home, and I’ll show you around?”
I followed her to her house, and it definitely had that new house look and smell. I tried to size her husband up from the pictures, since I’m being honest here, and I was trying to soak it all in. After she showed me around the house she asked me if I was up for a nightcap, and I said that I was. She grabbed a bottle of wine and a wine key and asked me to open it. She said that she needed to use the bathroom and would be right back.
Of course she wasn’t right back, but seeing her when she emerged from the bathroom was a real treat. Her black hosiery and the cleavage she was sporting from her mid thigh red and silky robe was an image that’s remained burned in my mind. I am sure that my jaw was dropped here. She was smoking hot and there was no way I could hide my emotions.
Finally she interrupted my thoughts and mock scolded me for not having poured the wine. I poured us a couple of glasses and she hit the switch to power on the gas fireplace. We sat on the couch looking at the fire, looking at each other, and talking about heaven knows what. I want to stress that back then I had been of the opinion that I’d meet a woman and get married. I was practicing my game and had never envisioned sleeping with a married woman. Sure, she turned me on. Immensely. I’d just thought it was date, court, get engaged, get married, and be miserable/bored/happy/whatever forever. I was highly conflicted and did not make the first move… at first. In fact, after I’d finished my glass of wine I told her that I had to leave.
I took both of our glasses, put them in the kitchen sink, and headed for the front door. She was coy about things, and I was having trouble reading her movements. I’d just cracked the front door open when I felt her hand on my shoulder. I turned and she was holding out her arms for a hug, so I pulled her tight and hugged her. When we broke out embrace, she held our her hand, and I grabbed it. I thanked her again for a great night, and was about to head out the door. Then I stopped again. I motioned to her with the index finger of my free hand, and planted a gentle kiss on her cheek, which she then turned into a full-on lip kiss. Lips to lips, her tongue to my lips, our tongues together. She pressed her body against mine, and I lost my balance backwards a bit. I ended up leaning into the door such that it slammed shut. She said, “good,” then broke our embrace and locked the dead bolt. Then she took my hand and lead me up to the master bedroom.
She told me to get undressed and as I did so she dropped her robe and laid spread eagle on the bed. She was wearing nothing but her thigh highs. I stood there naked and she said, “my god, you’re so big.” I assume she was talking about my stature because otherwise I’m pretty standard. Then she directed me, while holding my head so that my mouth was forced on to her pussy, to eat her out, and then I got my next surprise when she insisted that I eat her ass. I had never eaten an ass before, so I was kind of apprehensive. But I figured “when would I ever have this chance again?” so I dove into it, and it wasn’t nearly as bad as I’d thought. Plus her physical response to this, as she played with her pussy, was her squirting all over her bed, and my face and upper body. I had never seen a woman squirt before, and it was thrilling.
After she came down from her orgasm, she asked bluntly, “do you think you could cum in my mouth?” I was such a putz back then so I said, “uh, I guess. I’ll try.” Her mouth was fantastic on me, and I didn’t warn her but instead unleashed a fury of cum down her throat. She swallowed me as well as she could, and what she didn’t catch in her mouth she scooped up and ate. We laid side by side on her bed, and she told me that she wanted to fuck and asked me if I was ready to go again. Again, being the putz that I was, I said, “I think so,” and she asked if I’d brought condoms. Alas, no, I hadn’t brought any. She had some though and put the first one on me before insisting that I get on top.
We had a couple of quick rounds and two spent condoms before she got on top and started to control the pace. Then she started talking sexy to me. A lot. “Mmm, you’d like to fuck me without a condom, wouldn’t you?” “You’d like to put your hot seed in me, to show me how you do?” “You like to fuck another man’s wife, don’t you?” etc. I can’t say that I cried or whimpered, but in my head I was crying and whimpering about how hot this all was. As we fucked she kept coaching me about how to push and how she liked my balls slapping against her ass and so forth. The grand finale came when she said that she couldn’t wait to get back on the pill (or maybe even tell me that she was on the pill but would be lying) and that I’d be cumming in her “real soon.” I couldn’t go any longer, my hamstrings were screaming, and the more graphic her chatter the less I could concentrate. I finished and as I did so she grabbed my sack. Hard. It hurt but the pain of sack grabbage paled in comparison to the pleasure I received from that night’s last cum.
We dozed off and I woke next to her in the morning. She was propped up on one arm and was staring at me. “Does me being married bother you?” she asked. “Well, good morning to you as well,” I said. “It’s different. A lot different. I’m good with this if you are.”
“Oh, I think you know that I’m good with this,” she said. “The only question is what you want to do with this.”
I stammered a bit, and she told me that I should go. She went on to say that when I had a plan of action I should call her with a proposal, but not until then. We ended up “dating” every Tuesday through Thursday while hubby was away for work, and sometimes we’d have a quickie on the weekend (or two). We started going bare together and had our share of scares, but that’s not what ended the relationship.
I’d been at the mall on a Saturday afternoon, and who did I bump into? Sheba and hubby. I was super awkward. Hubby was all friendly and said things like, “I’ve heard all about you.” I just want into what I think he was proposing at the time, but in retrospect I should’ve gone with what I now believe to be interest in cuckolding and threesomes. It wasn’t until a few years after that I really got to enjoy those kinds of experiences to the fullest. Back then tho I just ignored her calls because I couldn’t deal with it. I even moved away.
Fast forward to 6 months ago, but who’s to friend me on FB but Sheba? I haven’t accepted her request, but she still looks amazing.
Source: reddit.com/r/gonewildstories/comments/9x3c8o/mf_is_there_anything_else_i_can_do_for_you
Damn that was hot. Why don’t you accept her request? Maybe she wants to be naughty with you again