It Started With an "Unusual Request" and THEN it got Interesting!

Nearly a decade ago, I went through a divorce and started dating for the first time as an adult. When friends suggested I write about my experiences, I started a blog. I have been "revisiting" some of my former exploits lately, and decided to share, using my real name, for the first time.

This piece was first published in April, 2013. Edits have been made for clarity and continuity.

Last fall, I received a rather interesting message on Plenty of Fish from a man who was…handsome enough to make me cautious. There wasn’t a photo associated with his public profile, but I require one in order for new contacts to message me. The picture he sends shows a handsome guy, small in stature, with salt & pepper hair, slightly Italian/ethnic features, a sexy, stubbly beard, and a good body. So attractive is he, that I question whether it's some sort of scam. A bit too sexy, you know? (I am nothing if not cautious.) He expresses an interest in me and says that he had a very particular request. I think “oh boy, here’s the part where it gets fucked up,” yet I dubiously encourage him to go ahead and ask. Worst case, I say no. No harm, no foul.

His response comes promptly, and he has a very specific desire. He wants to pleasure me. That’s all. He would like to rub my feet, touch me, massage me, taste me and make me cum for as long as I can take it. He doesn’t expect to have intercourse or for me to do anything other than to enjoy what he does to me. All he asks is that I be freshly showered and open to him pleasuring me.

Shut up.

This has to be a scam, right?

I find myself both suspicious and…cautiously intrigued. I tell him that I’m not sure that I would be okay with that. I say that I usually like to get to know someone a little bit before I am intimate with them. I ask questions: what do you get out of this? What about your gratification? Why me, specifically? He responds by saying that he would do whatever I wanted to make me comfortable. All I have to do is tell him what that is. He says that he is very gratified by satisfying someone else and that he has two other lovers that take care of his physical needs, but he is looking for someone that is willing to let go of control and let him give them pleasure. He chose me because he prefers my body type – curvy, voluptuous, womanly, juicy, responsive. This is what he likes. This is what he wants. I’m beautiful and he would love to pleasure me, but only if I am comfortable.

I basically blew him off. While admittedly intrigued, I couldn’t quite wrap my head around the notion of someone that good looking wanting nothing more than to…make me cum a lot. I mean, really – I kept waiting for the other shoe to drop. At what point would this guy tell me what his hourly rate was to perform said services? Because that’s what he looked like – a gigolo. And what he proposed was decidedly unusual compared to about 97% of men that I knew of. My suspicions and bullshit meter overruled any intrigue and interest that I had. I thought about it, but I did nothing more.

Several days later, I got another message from him. He wondered if I had given any more thought to his proposal and if there was anything that he could do to put my mind at ease. Instead of pressuring me, he became conversational. This actually served to make me quite a bit more relaxed. We talked about family, games, Star Wars & sci-fi, tattoos – just general getting-to-know-you-type chat. I found that I related to him on a human level, and I felt comfortable opening up to him about my history and reservations concerning his proposal. Which were pretty significant.

I explained that I had been with my ex since I was a teenager and that he really didn’t care for giving oral. This caused me to be not only inexperienced at receiving oral pleasure, but insecure about it. Because he didn’t enjoy it, The Ex also wasn’t good at performing it (something I now understand much better given recent experience.) He acted like it was a nasty chore that he had to do once or twice a year – like cleaning the garage. Try being uninhibited when your lover is practically holding their nose just to “get through with it” and making a face the whole time. Because he was so disinclined to do it, it always made me feel awkward, exposed, and dirty. My default feeling when receiving it was somewhat shameful, gross and “hurry up” rather than beautiful, desirable, hot, eatable, fuckable, juicy, delicious, sexy. Unsurprisingly, it was exceedingly difficult for me to come from oral. I finally had someone who liked it (and even requested it,) when we opened up our marriage six years before we split. That was the first time that I had ever been able to orgasm from a man going down on me. Cunnilingus had become something that I fantasized about but that also caused me anxiety and discomfort.

Also, I had spent most of my life taking care of other people – from my siblings through the illness and death of a parent, to my ex-spouse, my kids, my family – even friends & lovers. I was often the caregiver, and it was tough for me to be the “selfish” one. I loved being the center of attention, sure, but it seemed to be something that I clamored for rather than settled into. Lying back and enjoying wasn’t really my M.O.

Knowing this, and having a pretty clear understanding of my influences, fears & motivations made me all the more interested in trying to challenge myself with this tantalizing request. There was still a feeling like it might still be too good to be true, but I was becoming increasingly at ease with the guy & he was willing to meet for a drink to see how we got along before initiating bedroom activities. Okay, I think I can do this. Since it was an exercise in expanding my comfort, I didn’t even treat it like a date and may have added a casualness that made my new friend (let’s call him “Mr. Suave”) even more interested in me. We agreed to meet for a drink as soon as the playoff game that I was watching was over. It ran late, I was running late – we changed venues to my neighborhood because of the football game. I kept him waiting. He got there a little before I did but was in the bathroom when I arrived, so I saw him walk into the room. He was a bit short (as indicated in his profile,) but oh my God he was stunning. I mean – Calving Klein underwear model stunning. No kidding. His picture didn’t do him justice. Full lips, bedroom eyes, “good bone structure” to his face. Light beard – the fashionable and sexy kind – mostly white hair brushed back in that stylish/messy/effortless way. Not an ounce of fat to be seen on his compact body. Really. He was wearing jeans, a t-shirt and a light jacket and I was thinking that he looked too good to be real. His sunglasses added to the sexy impact, and I found myself again wondering how this could be legitimate, and if it was – what I did to deserve such a karmic gift.

He bought me a drink. I opted for a martini. I needed the booze to center myself and calm my nerves. He had a white wine. We talked. It was relaxed. I liked him. As our “not date” progressed, I found little moments of surprising affinity. This was supposed to be a dark & dirty emotionless hookup, but we kept laughing and agreeing, and would glance up and smile like “oh, we like each other – hi.” It was really interesting. I mean, we’re the same age and had similar backgrounds & interests. We talked about our jobs and families, childhoods, parental disapproval, etc. His parents are Italian and Mexican respectively, and his dad is disappointed that he is not married and settled with kids. His mom is recently divorced and living alone for the first time. She and I share this commonality. I have a feeling that Mr. Suave doesn’t usually get this personal with women that he wants to “service.” I feel like we’ve broken a rule and are forging new ground. We like each other.

The third time the bartender checks back to see if we want another round, he settles the tab. I invite him to my place. He follows me home. He’s great at being relaxed and calm. He can direct and lead without being pushy. It’s a gift. We sit in the living room on separate pieces of furniture. He makes it casual. Comfortable. Relaxed. He’s not rushing, or draping himself over me on the couch – he’s at ease, sitting in a chair across from me – chatting amiably. I do a shot of chocolate vodka & tell him that I’m suitably infused with liquid courage and ready to try this. He asks if we should go to the bedroom. We should.

I light candles & we put on some music. He asks me to get comfortable. I take off my boots. He rubs my feet. I say that I would be more comfortable without my jeans on. He suggests that I should lie on my stomach so that he can give me a massage if that’s okay. Yup.

Oh my God, he feasts on my body. Slowly. Deliciously slowly. My feet, my toes, my knees. He smells the flesh behind my knees. He breathes me in, inch by inch. He delights in ALL of me. Eventually, achingly slowly, he works his way up to my ass. He rubs, smells, gently bites. He plants his face between my legs and just breathes. The moisture of his breath mingles with mine. The anticipation is an ache – but now that I’m relaxed, pliant & willing he doesn’t make me wait. He asks permission…he pulls cotton & lace aside. And goes the hell to town. Jeeeeeeeeezus. The man lives & breathes pussy & orgasms.

At some point in my muzzy haze of cumming repeatedly, I realize that he’s taken his shirt off. I mean, that’s the sort of serious business he’s at down there – since he’s in up to his shoulders he apparently doesn’t want to get his shirt messy! I should point out that I am being thoroughly worked over by tongue, teeth, fingers & face but I think I came again when I saw this man without his shirt. Holy hell. Did I say underwear model? He was RIPPED – arms, shoulders, back, abs. I have never been with anyone whose body was so sculpted. Ye gads!

After a few thousand orgasms I finally let him know that I needed a break. I was flooded – overwhelmed, exhausted, spent & satiated. I actually prefer vaginal penetration in bringing me off, and I would have loved to ride his cock for a while, but that wasn’t part of our agreement. While we were lying back on the bed catching our breath, however, I heard the sound of his belt being unbuckled and looked over to see him loosening his pants. Oh, okay. I guess he was aroused after all. That’s kind of nice, right? Good feedback, hmmm?

Mr. Suave is now very subtly rubbing one out and I reach over and encourage him to take his dick out. Oh boy – oh wow, it’s a beauty. I help him get it out and offer a little assistance. Taking him in my mouth seems to be the least I can do for this man who left my lying in a puddle of my own girl goo. He responds very positively to my sucking his dick but there’s a sense that he’s holding back a bit. Maybe this was simply because we were “breaking the rules” of our arrangement. I don’t know. It felt like we’d already gone from this…indecent proposal to…a sort of interesting affection & commonality. It already felt like the "rules of engagement" had been broken.

I turn my full attention to his rather lovely cock. He hesitates to even take it all the way out of his pants. It’s as if he knows that he’s not “supposed” to. I have a difficult time articulating his hesitation. Everything between us had been very organic, comfortable, natural – even fun & friendly – unexpectedly so. Now here we are, two adults who are attracted to each other and interested in each other as people and...it seems as if he doesn’t to want to impose. I would really like for him to impose. I suck his dick and cup his balls. He moans and arches his hips, but after a few thrusts he pulls my head back and instructs me to just use my hand. Together, we finish him off in a hand-over-hand fashion & I clean him up with a towel. We both get dressed, he thanks me saying it was perfect, and that he hopes that we can do it again sometime soon. Okay. Okay. Okay.

As he leaves me in my robe, barely able to stand from the jiggle legs, I watch this incredibly beautiful man walk away and think that this is must be what it feels like to have been serviced by a professional male prostitute. Seriously. He was that pretty and it was that good and focused so much on me and my pleasure. I HATE that I still had a little niggling voice in my head that wanted to know “what’s the catch?” I actually wondered if maybe this was a new gigolo technique stolen from the drug dealers – the first taste is free & then you’re addicted! It was spectacular, but there was still a little something that seemed slightly…off…I decided to chalk it up to my insecurities, his physical beauty, his particular “kink” and the fact that we were new together. Essentially, I talked myself out of being concerned, and decided I would just enjoy it without hyper-analysis!

And that, my sweeties…is my first cliffhanger…because there is more to this story, much more. I promise to write about it very soon, but this entry is already huge, and the rest of the story is a tale unto itself!

STAY TUNED!

Okay, I won’t even make you wait! Here’s the rest of the story!