Meet Oil Man

April 27, 2016 Wednesday

[If you haven’t read yesterday’s post about my initial messages with the Oil Man, pop back there.]

7:30 am Groggy start

I woke up feeling crappy after only 5.5 hours of sleep. I needed time to sleep more.  I  decided I was going to meet the Oil Man and needed time to prep, so I stayed home from work and went back to sleep for a couple of hours.

We spent the day texting – a fun time revving each other up in the morning, around lunch time, and when I was on my way to him.  He makes me smile.  So charming!

5 pm Heading downtown

I took a long shower, shaved, and clipped my toenails!  I got dressed up, tossed two vibes and a bottle of olive oil from my kitchen into my purse.  Hubby dropped me off at the subway and I went downtown.

5:35 pm Meeting

I took a seat in the lobby of his hotel, the Oynx, and texted him. He popped down and gave me a long hug with a quick kiss. He sat beside me. He had on a lovely dress shirt – white with blue stripes – and khakis. I wore my usual “Sassy goes to meeting” outfit – blue button-front top with a silk scarf, blue slacks, black bra and panties, socks and clogs.  He had thick white hair!  He looked better than his photos!  He looks sort of like an older Jon Stewart, the former Daily Show host.

Jon Stewart

He tried to talk me into going right upstairs with him to his room, but I held out for eating something first. And I wanted a little time to get to know him, decide if it was safe to be alone with him.

5:45 pm Dinner

My older sister had recommended The Causeway, a pub around the corner.  They put us in a big booth along the side wall.  It was the wrong place for this night – loud music, small selection of food – but I toughed it out.

I ordered a pulled pork sandwich with corn bread and potato salad. He had a couple of ribs and the rice & beans.

We had a good conversation on a very shallow level. He flirted with the waitress.  He paid. I asked if he wanted some money from me – he laughed and said he was going to expense it. He went to the men’s room and I peeked at the check – only $30.

6:30 pm “Dessert”

He asked me if I’d like “dessert” in his room. I wanted to and he seemed so sweet and safe. I took the chance. I know… I’m an idiot. I was hoping the law of averages would be on my side this time.

We did some fierce kissing and groping in the elevator, then went to his room #709. The room was new – a renovation of an old office building. It was tiny but had all the basics – king size bed, open metal shelving rack against the wall with closet section, fridge and microwave, flatscreen TV. I set out the olive oil and two toys he’d requested – my little silver bullet and my big silver bullet with a couple of extra batteries – on the night stand on his side.

He helped me get undressed – not in a romantic way but just helping me with a task to be done as quickly as possible. Better than each of us doing it ourselves, but not my preference. I got my first look at his body… cute little ass, muscular arms, elegant hands, a little pudgy tummy and a tiny penis… hoped that was just that he wasn’t excited yet, but it certainly would be easy to deep throat!

He took my hand and led me to the bed, moved my arms and legs around and had me roll over onto my tummy lying across the bed. He poured the olive oil down my spine and massaged it into my skin. I was skeptical, but it felt wonderful and it didn’t smell. I relaxed and enjoyed his hands working my muscles. He took the little silver bullet and pressed it inside me to do its work while he rubbed the oil down my legs.

He tugged on my arm and rolled me over. I wished he’d just say when he wanted me to move… it felt odd to be shoved around. He got up to get his belt and a small towel from the bathroom. He tied my hands gently over my head then covered my eyes. He took more oil and drizzled it on my face around my lips, my neck, my chest, made a little reservoir in my navel, then dripped some down my slit and onto my upper legs. He returned to my chest, sucking and nibbling my nipples, working the oil into each breast and my tummy, pulling more from my belly button to spread lower. Oh my! He nibbled and licked my clit, and moved the toy around. It felt good at times and hurt at others, but never much for long.

He stopped, untied my hands and ditched the blindfold. He pressed my head down to his cock. He held my head and fucked my mouth. I thought, “If you let me run this part, you’d have a lot more fun,” but I just took his cock in and out. He was not hard at first. That surprised me. Most men in full play mode are pretty stiff. But I got him there with my hands and mouth – sucking, pulling, twisting. He grew to a very pleasant size! Right about the time I thought I could take him over the edge, he pulled out and collapsed beside me.

I wondered if he was a cum-once-and-done fella so he was saving himself for vaginal sex. After a couple of moments, he crawled on top of me and shoved his cock down my throat while he sucked on my clit. 69 is not my favorite thing, but I rolled with it, taking him in and out, groping his ass. I thought I couldn’t breathe between his weight on me and his cock so far down my throat, but he let up after the second time I gagged.

8 pm Snuggling

He pulled out, and turned around to rest his head on the pillows and pulled me to nestle on his chest. He closed his eyes and fell asleep! I was puzzled. I thought about getting up to pee and check my phone but I stayed there awhile, listening to him snore quietly and enjoying being snuggled up next to him. He had soft, sexy white skin.

Finally I had to pee. The moment I moved he woke up. I told him to go ahead and sleep, I was just going to the bathroom. I left the door open and he talked to me while I marveled at the marble shower with full-size dispensers of shampoo, conditioner and shower gel! He beckoned me back to bed and I had hopes of more sexy stuff, but he returned me to snuggling mode and started asking me questions. He wondered if I had to go soon, didn’t want me to get in trouble. I said I could stay awhile. We talked about his favorite musicians, more about my visits to his part of the country, his early life.  There is such a difference between his sexual and non-sexual self.  During the sexy stuff, he is quiet and dominant and kinky.  Before and after, he was the perfect gentleman, sweet and cuddly and chatty.  Hmmm….

I rubbed on his cock but he didn’t get hard. Hmmm… is he really going to let me go without ever cumming?  Can he cum?  I kept asking questions, telling stories…hoping we could do more and he could cum.  He is so easy to be with when we’re talking!

10 pm Heading home

I finally gathered there wasn’t going to be anything further in a sexy way… I am so dense about that. I dressed while he reclined in bed watching me. He got up to hug me good bye – kissed me once with a peck on the lips then held my head and pecked me on the forehead. Then he let go, patted me on the ass and opened the hotel room door for me.

I went to the curb, requested a LYFT ride using the app on my phone. The car came in less than 2 minutes and I was home by 10:15 pm.  I texted him to let him know I made it, and he replied quickly, thanked me for a lovely evening.  Classy.

So I managed to have a nice evening, if a bit strange with the olive oil and so forth.  Phew!  The law of averages was in my favor at last.

Will I ever hear from him again?  Hard to tell.  In some ways, it’s fine if I don’t. In other ways – he was a real sweetie and it would be great to touch him again. Luckily I am not going to pine. It was a nice distraction!

Oil Man

April 26, 2016 Tuesday

I talked with a new guy today!

With Philip nearby and not finding a way to see me, and not having seen The Northerner in over a month, I was going crazy.  I get desperate when I haven’t had sex for over a month.  This is when I tend to do stupid things.  
Tuesday afternoon I needed a distraction in the middle of a busy day at work, so I decided to log in to Ashley Madison to see if there were any new men to read about. A guy winked at me right away, so I looked at his profile. It was pretty good!  He’s about my age, my height, cute face, with beautiful thick white hair!  A bit wordy. But he’s kinky. And he’s from New Mexico. Why is he writing to me from so far away?  I moved along. 
Then he sent me three messages! 

Ashley Madison messages 
Date:  Apr 26th – 1:17pm
From:  Oil Man
Hello Sassy! 
I love your profile, I know I’m not 6′ but I do so love curvy busty women that I have 2say hello. I am in Boston on business right now and passion is a wonderful way to spend a moist and chilly bit of time don’t you think? . . . Tim
Date:  Apr 26th – 1:25pm
From:   Oil Man
I also love that we are BOTH Nonsmokers!!
Date:  Apr 26th – 1:26pm
From:  Oil Man
Good kissing ahead (I hope)
He writes well!  I looked at his profile again – so he’s in town on business. I tried having dinner and playing with a Traveling Man once about three years ago, and have mostly decided it’s not my thing. But it couldn’t hurt to flirt, right? And if he wrote me, I should write back. It’s only polite, right?


Date:  Apr 26th – 1:28pm
From:  Sassy
Hiya Tim, 
Thanks for your note and for reading my profile. Today I am definitely wishing I could’ve stayed under the covers with someone. Too bad I have to be in the office! At least I can flirt a little over lunch. Three quick questions. (I am curious as well as Sassy.) 
1) When you say “in Boston” are you in the city or out in the burbs? 
You don’t have to say where exactly. 
2) Are you here for a once-for-a-week gig, or longer term, or here now and then? 
3) How old were you when you first had sex? 
Hugs with groping!  -Sassy
Date:  Apr 26th – 1:33pm
From:  Oil Man
5am by the Tip O’Neil Federal Building off Sudbury. 
I am here for a conference, leave Thursday noonish. 
Date:  Apr 26th – 2:13pm
From:  Sassy
Hiya Tim, Sorry this is not my style. I’m more a long-term gal. Best of luck with the buxom Boston beauties!
Date:  Apr 26th – 2:13pm
From:   Oil Man
OH NOOOOO !!!! You’re dumping meeeee!!!
Date:  Apr 26th – 2:19pm
From:  Oil Man
Take care lovely one. 😉


So we exchanged messages and it turned out this is an honest offer for a one-time thing. He’s only here until Thursday and doesn’t come to Boston much. So I thanked him and sent him on his way.

He was very sweet about being upset about that, and quite gracious. I smiled the whole rest of the day thinking of how fun that was, but glad I didn’t go further. One-night stands are not my style. Being with The Traveler three years ago was odd, and the only other time I met someone after a quick correspondence, he attacked me. Just not worth the risk.  I was sad… he seemed so nice! There was this spark… Did you see it?  *sigh

Later in the evening he wrote back.

Date: Apr 26th – 5:47pm
From:  Oil Man
Damn. You sounded perfect . . .


I smiled but resisted answering.  I do not want to be tempted to do something foolish!

But the words stuck with me… and right before I was closing up my computer to go to bed, I couldn’t resist writing him back.


Date:  Apr 26th – 11:49pm
From:  Sassy
Awww… I hear you. Thank you for saying. I am smiling over your messages…wondering.
Good thing we stopped while we still think it’s perfect! 
Date:  Apr 26th – 11:51pm
From:   Oil Man
Not goid at all, you still seem to be perfect
ah, sighhhhhh
Date:  Apr 26th – 11:52pm
From:   Oil Man
Good nod goid, perfection is unreachable. 
But it is so much fun to try
Date:  Apr 26th – 11:54pm
From:  Oil Man
And me here in a secret live nest, king size bed, 
Date:  Apr 26th – 12:02am
From:  Oil Man
Secret love nest, that is, 
damn phone
My fingers need to lose weight
Date:  Apr 26th – 12:05am
From: Sassy
Want to talk on the phone? 
Torture ourselves further in another medium?
Give your number and I’ll call.  
Date:  Apr 26th – 12:06am
From:  Oil Man
I would love to!! 
[his mobile phone number]

I asked if he’d like to talk on the phone. He was so pleased – sent me his number right away. So I called him. He has a beautiful voice and speaks well. We talked for two hours! He was easy to talk with, and a good listener – let me ramble about my trips to his area, and I let him tell me about his fantasy to give a gal an olive oil massage with mild restraint and blindfold.  Never heard of using olive oil!  It sounded strange but harmless enough.

He used the word germane at 2 am! He begged to meet me. Breakfast? Lunch? Dinner? I finally agreed in principle to a 6 pm dinner date near his hotel, but asked him to check with me in the morning.

He asked me to bring three things – a small amount of olive oil and two vibrating toys. He had shared five photos, so I sent him four photos – my cleavage in a new bra, a nipple shot, a panties shot and finally… my face at lunch last January!  He didn’t run screaming.  Phew.

I went to sleep with a smile on my face and a tingle between my legs!