02
Apr
13

It Started With an “Unusual Request” then got interesting…

Sometime last fall, I received a rather interesting message on Plenty of Fish from a man who was…handsome enough to make me cautious. He didn’t have a photo associated with his public profile, but I require one in order to message me. His one photo showed a handsome guy, small in stature, with salt & pepper hair, slightly Italian/ethnic features, a sexy, stubbly beard and a good body.  He was so attractive as to make me question whether his was a legitimate profile or maybe some sort of scam. Too pretty, you know? (I am nothing if not cautious.) He expressed an interest in me and said that he had a very particular request. I thought “oh boy, here’s the part where it gets fucked up…” and cautiously encouraged 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 comfortable with that. I say that I usually like to get to know someone a little bit before I am comfortable enough to be 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 do this for him. 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 degree of 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 anymore thought to his proposal and if there was anything that he could do to make me feel more comfortable. Instead of being pushy or pressuring me, he got conversational. This actually served to make me comfortable. 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 like it, the ex wasn’t good at it (something I now understand better given recent experience,) and he acted like it was a nasty chore that he had to do a couple of times a year – like cleaning the garage. Try being uninhibited when your lover seems to be holding their breath just to “get through with it” and making a face the whole time. I don’t want to be mean, it just wasn’t his thing and therefore, I was inexperienced. It made me feel awkward, exposed, vulnerable. My default feeling when receiving it was somewhat shameful, gross and “hurry up” rather than beautiful, desirable, eatable, fuckable, juicy. Unsurprisingly,  it was very difficult for me to come from oral – I had 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 managed to become something that I fantasized about but that also caused me a little bit of anxiety and discomfort.

Also, I had really spent most of my life taking care of other people – from my siblings through the illness and death of a parent, to my 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 MO.

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 this might just be too good to be true, but I was becoming increasingly comfortable with the guy & he was willing to meet for a drink to see how we got along before even considering 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 casual aloofness that made my new friend (S42 – let’s call him “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 a 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 little 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 just looked too good to be real. His sunglasses added to the sexy impact and I found myself once 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 – like 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. We share this commonality. I have a feeling that he generally doesn’t 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 settled 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 draping himself over me on the couch – he’s sitting in that chair – looking at me and talking to me. I do a shot of chocolate vodka & tell him that I’m 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 kind of serious business he’s down to 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 do still have a preference for actual vaginal penetration in bringing me off and I would have loved to ride his cock for awhile, but that wasn’t part of our deal. 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 hasn’t even really taken it all the way out of his pants. It’s as if he knows that he’s not “supposed” to. I have a hard 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 really attracted to each other and interested in each other as people and…he doesn’t seem to want to impose. I would really like 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. We finish him off in a sort of hand-over-hand fashion & I clean him up with a towel. We both get dressed, he thanks me saying it was perfect & says that he hopes that we can do it again sometime soon. Okay. Okay. Okay.

Seriously – 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 essentially what it must feel like to have just 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 very specific “kink” and the fact that we were new together. Essentially, I talked myself out of it & 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!

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2 Responses to “It Started With an “Unusual Request” then got interesting…”


  1. May 12, 2013 at 3:59 am

    Reblogged this on risquédivorcée and commented:

    I’m reblogging this because it is not showing up in my recent posts feed & it only had four views so something’s wacky!

    • 2 jld
      May 12, 2013 at 9:36 am

      Whaaat? Come on what’s the catch? I always felt that oral, and physical touch were pert of the promise when being intimate with your partner.

      J


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