Starting Over

It pissed me off a little to think how Lisa and Jolene had more or less taken over my life, but on the other hand, if I could get the 'tips' she was talking about, hell I'd be able to go anywhere I wanted, how I wanted, and all the begging for minimum wage work would be over.

Sensing my aggravation she said "Admit it Art, don't you find it erotic to hear that two women have been discussing your sexual prowess and attributes. Speaking of attributes, I got the report from Doctor Henley. Good grief, 7 and 3/4 inches! I've never had one that big in me!"

There was only one answer to that: "My place or yours?"

"Unfortunately, neither. You've got a date at seven-thirty this evening and we have to get you some suitable clothes."

I swallowed with disbelief.

Fortunately traffic wasn't too heavy on the Beltway so we got to Towson Center in less than 30 minutes. There at Nordstroms I got fitted out with a brand new navy blazer, blue and white striped shirt, tan slacks and dress shoes. Then we left the shopping area and whizzed over to the nearby Best Western. There, parked within sight of the entrance, Jolene proceeded to give me some instructions.

"Your date, Denise, will meet you in the lobby. She has light brown hair, no glasses and will be wearing a blue dress. Tell her you're 'Ralph' and give her this J & B Associates card. She needs to say that she's 'Denise' so you know it's her for sure. Make small talk and ask her out for dinner. There's a bistro named '7-Extra' in Towson Town. You'll need to call a cab to get there and back. I have the feeling she's never done this before so you may have to work hard romancing her. And remember, don't charge less than $300 for an extra hour."

With that, I got out and Jolene drove off leaving me to take on work I'd never dreamed of getting.

Inside the Best Western lobby, I saw a late 50's woman in a blue dress, looking somewhat tense. I introduced myself and gave her the J & B card.

In a shaky voice and not really looking at me, she said "I'm Denise. So nice to meet you."

I knew I had to put her at ease and quickly so I just sat down next to her and told her that the 7-Extra bistro in Towson had been recommended to me and made up a bunch of shit about how good my friends said it was.

"Well Ralph, I'm not from here so I'll let you take the lead on that."

"I'm going to have the concierge call a cab." I didn't want to give away that I didn't have a car so I continued "That way there's no worry about a second glass of wine."

Already during the cab ride, she seemed to be calming down somewhat and by the time we were seated in the bistro, we must have looked like a normal couple. Of course she couldn't resist asking about me so I told her that I had a small home improvement/maintenance business and due to a bad divorce, I had to supplement my income.

She told me she and her husband, a cardiologist with a big practice, lived in a small city in southern Pennsylvania. That of course reminded me that I wasn't all that far from Chester, where I'd had to leave in a big hurry, but I put that aside and got busy with small talk. We had a nice meal with pleasant conversation and afterwards, sipping wine, we still hadn't discussed any tip related service. I had to start some way so I asked her if she was in the Baltimore area for shopping or entertainment or just visiting.

"Actually both. As far as my husband knows, I'm here to shop for my granddaughter's birthday. Ralph, I'm nearly 60, overweight and well, this is not so easy to say, but my husband has a big practice. Well you've probably heard stuff like this before -- young nurses, hard work. I try to shut that out by doing lots of community work but sometimes, I think about other things, have fantasies. You understand?"

The word 'fantasies' was all the opening I needed and it didn't take too long to find out what her fantasies were. To my great relief, her fantasies didn't include any really weird shit - quite the opposite actually. Just talking to her about the fantasies gave me half a hard-on. Under the table, I put my hand on her thigh and she responded with a quiver of pleasure. We pretty quickly came to the agreement that she would pay me $600 to spend the night with her in her room. We skipped dessert and there was still some wine in the bottle when we left.

Back at the hotel, we took the lift up and in the hallway, Denise handed me the key card to her room. Inside the room, actually a suite, right away she took six hundred-dollar bills out of her purse and handed them to me. Then with a naughty smile "Now that's out of the way, let's get back to our date."

I helped her off with her jacket and while I was hanging it and my blazer in the wardrobe, she went on into the suite. I found her standing in front of the dresser facing the big mirror over it. Taking a stance right behind her, I placed my hands on her hips and began by softly kissed her neck. At the same time that I expanded my kissing to her cheeks and ears - whatever I could reach - I moved my hands down over her hips to the bottom of her butt and the back of her thighs. Then back up the same way, my hands went on up to the flanks of her chest to graze the sides of her generous soft breasts. Then down again repeating the same thing several times before changing the routine to my hands moving forward over her hipbones and down to the front of her thighs. On the up movement, I then ran my hands under her breasts and hefted them slightly. All the while Denise was oscillating her head ever so slightly and softly swooning as her breaths became more and more audible.

I had to let her know how I was doing so I held her hips and pressed my groin against her back so she could feel my hard-on. Taking her wiggling butt and continued swooning as encouragement, I reached up under her dress with both hands and stroked the front of her pelvis before moving to her vulva. Massaging her pubic area, I could feel the moisture through her panties. Leaving one hand to massage her pussy, I used the other to massage her tits. Both of us were still fully clothed but that had to change.

Whispering something like "I'll be back", I took my hands away from her pussy and tits and used them to unzip the back of her dress, unsnap her bra and pull down her panties. Now with free access, I massaged her tits and fingered her now very wet slit. When her hips got to oscillating so violently that I could barely keep my fingers in her pussy, I whispered in her ear "Denise, close your eyes and wait, I've got a surprise for you!"

I got two pillows from the bed and laid them on the dresser one atop the other. Then I undressed completely and again got myself tight against her back. She responded immediately: "Ralph, I can feel your hard penis against my back. I think it wants to be inside of me." With that she bent over the dresser, elbows on the pillows and chin in her hands, and looked at herself in the mirror. In her bent over position, her pussy presented itself and I worked the head of my dick in between the lips and sort of worked it around to really get her ready. When she let out a pleasured moan and thrust her ass back, I knew that she wanted more. A light thrust of my hips and I had it halfway into her and began fucking her with slow short strokes. Bending over a little further, I took her tits in my hands and massaged them while I fucked her. In the mirror, I could see her pursing her lips and closing and opening her eyes, all the while swooning softly. Occasionally and especially when I made a deeper thrust, her swooning would be interrupted by a light squeal that I took to mean that I needed to be careful. At dinner, she had as much as said that her cardiologist husband hadn't fucked her for quite some time.

I was getting close and I needed more so I pushed deeper and was surprised when she uttered something like "Ralph, yes Ralph, fuck me deep! Fuck me hard! I want your whole dick in me now!"

That was all I needed to really get in gear. At the same time, I wondered if I'd be able to hold back long enough so she could cun too. Feeling the pussy juice on her thighs at the end of my in-strokes told me she was close but I still wanted Denise to climax first. She let me know that wasn't necessary: "Ah, ah, ah, don't hold back, cum inside me now! I want to feel your hot cum in my pussy!"

I let go of her tits, grabbed her hips and thrust even more madly. Then came the volcano. Denise reached back with both hands, held my hips and dug in her fingernails. The fresh flow of warm liquid that I felt go down my legs must have been our combined production.

After the eruption, her hands on my ass cheeks and her earlier fantasy confession told me I needed to leave my soft dick soak inside her and at the same time knead both of her tits with my hands. We stayed locked together like that for what could have been five minutes. I was beginning to feel like I might get hard inside her when she let go of my ass cheeks and stood up. My still soft dick slipped out and some more semen dripped on the rug.

"Ralph, we should've put a towel on the floor first."

"I had other priorities -- like getting my dick in you as fast as possible."

"You're so romantic."

"You're the first to tell me that. We could just spill a drink on the rug as camouflage. Shall we go shower together?"

"Yeah, and afterwards let's use the tub spa in the bedroom. I'll start running it full now."

In the shower, we did an extra good job of soaping and washing each other. It turned out that both of us really got wound up when I got behind her, hard-on against her back, and played with her soapy tits. Denise was overweight but sort of comfortably so. She definitely had a belly but it didn't overhang. In a way it was sort of erotic, the way it stood out hiding a view of her pussy from close and above. Right away when we met in the hotel lobby, I noticed that her hips were fairly wide but that just seemed to make her look more feminine. Her extra weight had two more advantages: It hid wrinkles in her face and it made her tits bigger. In fact her tits were too big for me to enclose in my big worker's hands. In the shower I was really grooving on soaping them, rinsing them off, hefting them and then bending around to suck on her nipples. Just the thought of tit fucking those bazookas made my hard-on complete.

Still rock hard when we rinsed off, I would have fucked her standing up in the shower but she let me know that she had something else in mind. Still hard when we dried each other, I was surprised when Denise held a cold washcloth on my dick to slow me down. Then I remembered the tub in the bedroom and another of her fantasies.

In the tub we sat facing each other, her legs over mine. Considering that her husband hadn't fucked her in years, it was no surprise that Denise had a fantasy about being pampered. Her arms spread on the sides of the tub, her head back and eyes closed, she let me take over. I lifted her mid-section to bring her crotch just out of the water and buried my face in her generous crop of light brown pubic hair, at first kissing superficially then becoming more specific by licking the slit. She, wanting me to use my fingers as well as my lips, moved her feet so as to support her mid-section in the dining position. I spread her lips with the fingers of one hand and raised her hood with the index finger of the other.

She had told me earlier that her husband had never come anywhere close to fulfilling Denise's lifelong fantasy of having her inner and outer lips licked while her clit was being massaged. Determined to fulfill that fantasy and even more, I supplemented the licking by getting the tip of my tongue in her vagina. After looking up momentarily and seeing her fists clenching in ecstasy, her eyes still closed and her mouth opening and closing; hearing her scream and feeling the flow of juice hitting my tongue came as no surprise. Then she was quiet as her mid-section settled down into the tub. I had the impression that she had even lost consciousness -- at least momentarily.

After what seemed like a few minutes of her being out of it, she looked at me with a very contented and inviting smile. In fact her smile was so inviting I wouldn't have needed to remember the rest of her fantasy to know what to do next. I got up on my knees and took her generous breasts in my hands, squeezing ever so lightly. Denise leaned forward and with her lips touching the head of my dick, she took it by the shaft with one hand and held my balls with the other. Knowing what was coming, I made up my mind to hold back so she could live out the rest of her fantasy. With the hand she had on the shaft, she pulled skin forward so it bunched up over part of the head. Then with lips pursed open, she moved her head forward so as to push my foreskin completely off the head. At the end of that motion, she would flick the head with her tongue. I was beside myself. She kept to that fucking like motion, pushing the foreskin back and then letting it slide forward as her head retreated, for what seemed like minutes. Adding variety to her blowjob, she used her left hand to hold my foreskin all the way back, like as if I were circumcised, and then she gave me a mouth fucking with as much stroke as the size of her mouth allowed. That did it. My first squirt went in her mouth. When she drew back, I thought I'd overestimated her capacity for kinkiness but she quickly interjected: "Ralph, in my face!" One jerk of her hand and a white blob was slithering down one side of her nose and over her lip to join the blob that was already on her tongue. Then she buried my dick between her tits and kneaded them so vigorously that I shot the next and last wad against her breast bone.

She let me get soft between her tits and then lay back against the end of the tub. After spreading and massaging my cum on her neck and breasts, she gave me a coy smile and said "Ralph, I bet you're holding back on me."

I answered her by looking down at my now hanging member.

"Ralph, my doctor husband might not be fucking me anymore, but being married to a doctor, you do learn lots of physiology of the male reproductive system." Then taking my soft dick in her right hand, she milked the rest of the come out onto her left hand and likewise spread it on her upper body.

Completely spent we both sunk into the tub and soaked and dozed. Waking to cooling water, we platonically washed and dried one another before going to bed naked and spooned together. Before dropping off to sleep, the question crossed my mind: Would I be able to service her again in the morning?

Hours later, I woke slowly to sun streaming in between the curtains and even more slowly realized I was no longer in the spooned position with Denise. Instead, I was on my back, the cover was down and she was sitting beside me, looking alternately at my face and at my groin. My still soft penis was in her right hand. "You don't mind me fondling you do you Ralph?"

I answered with what I thought was look of assent and anticipation of pleasure and that is the way Denise took it.

"Ralph, you have a really big penis. Oh I'm sorry, but you don't mind me saying that do you?"

"Denise, men like a woman to tell them they've got a big one -- especially if they don't."

But you really do have a big one. It's bigger than my husband's. I could never get two hands on his shaft. Yours, I can't even cover with both my hands. When we were dating and the first few years we were married, I used to give Mark head. His penis would go all the way in my mouth. With you, my lips don't even get halfway down."

I told her it was nice to be liked and I was glad she liked me. Then it occurred to me, Denise was begging for a compliment so I told her how much I liked her big tits and how good my dick felt inside her pussy.

Her fondling hand and the conversation were taking their toll. "Ralph, you're getting hard right in my hand." Then she bent down and gave the head of my dick a long smooching kiss. Rising up again "Ralph I'm glad you're not circumcised. I like how I can make the head appear and disappear."

I was about to ask her if her husband was circumcised but before I could, she volunteered the information without my asking. "My husband is circumcised. But honestly, that isn't really the problem. But still, I really like playing with yours."

As if the fondling and talk weren't enough, Denise bent over, retracted my foreskin again and thoroughly licked the whole head of my dick before twisting her head and moving down and kissing and licking the shaft. That's all it took. I was rock hard. Thinking she wanted to give me a blowjob, I continued lying on my back but that's not what she had in mind.

Leaving one hand on my dick, she rose and snuggled her head up to mind and with a deep sexy voice asked "Ralph, could we just do it -- I mean the regular way? You know with you on top? Just use me! Really put it to me!"

So she wanted more aggression on my part and what she said and the way she said it put me in an aggressive male mood. I rolled her over on her back and before she had a chance to spread her legs, I spread them for her and got on my knees between them. My arms under her knees, I raised her legs so they were on my shoulders and entered her immediately and went in all the way. Her eyes were wide and her mouth open. Her tightness around my dick and her gasp told me she wasn't completely ready so I backed off and fucked her slowly and going only partway in. This brought on a happy relaxed smile and we slowly got into the routine of a good friendly fuck -- laughing, teasing, joking, talking dirty.

Sometimes I played with her tits, other times I held her hips and fucked with a maddening tempo. Obviously she wanted it to last because she kept breaking off the mad tempo by pulling my hands off her hips and on to her tits. Then even Denise couldn't hold back and I felt the warm flow on her ass cheeks. For me the time had come as well and I shot a nice wad and collapsed on top of her.

Afterwards, we showered together and she milked me out. I only got half a hard-on and Denise realized her night was over. I hoped she thought she'd gotten her $600 worth.

After drying off and getting dressed I got my answer. She gave me hundred dollar bill as a tip for what she called 'extra attentive service' and said she'd ask for me next time she went 'shopping' in Baltimore.

Elated with having made more money in one pleasurable night than I had made in almost two weeks of handyman work, I took a cab back to the strip mall where my apartment was and gave the driver a generous tip.

Inside, the efforts of the past night began to catch up on me so I went to bed and more passed out than went to sleep.

Saturday

The doorbell brought me out of my deep sleep. Still in my shorts and tee shirt, I peeked around the door to see Jolene's secretary, Maureen, standing outside. "Jolene wants to see you -- say around 1:30. And wear your blue blazer and a nice shirt!" Looking at my watch, I saw it was already 1 PM. Remembering my new and easily acquired wealth, I couldn't help but agree to be there.

At the office, Jolene told me she'd already heard from Denise and that there'd likely be another date the next time Denise came 'shopping' in Baltimore. There wasn't another date lined up for me yet, but I did get told to go to a nearby BestBuy and get a mobile phone with a prepaid SIM and come back right away to give them the number. A half hour later, when I came back with my newly acquired electronic wonder and gave Maureen my number, there was another woman there. She turned out to be a local photographer who Jolene had hired to make a website photo of me. I didn't agree to this until they showed me that the facial features of all their 'models' were blurred for the website. When you think about it, yeah, the clients have to have some idea what they're getting, even if it's not 100% in detail.