Small Town Gigolo Ch. 02

Please read the first part of this series before continuing.

*****

Before I married the woman of my dreams I was a Gigolo, male whore, prostitute, whatever you want to call it.

My beautiful wife died of breast cancer aged 62 so I here I am now in my thirties heartbroken and now penniless, we had lived in her house which passed to her sons on her death and I moved out not wanting to stay in the house where all the happy memories were. I rented a small flat on the other side of town, and now as I had been fired from my job because of the time I had taken off grieving for Margaret I was skint.

My mum was actually my step mum, my real mum had me and then dumped my father as soon as I was born, I had been born out of wedlock and her parents were very religious and didn't want anything to do with a bastard child, and gave her a choice, the bastard or them, so being the selfish bitch was, wanting to keep her inheritance dumped the pair of us.

I needed to earn some money and fast, so I went back to what I knew how to do, and that was shag older women senseless. I needed to get word back out in the market place so I needed to see my former agent/pimp Molly. She was now in her early 60's but didn't look like she had changed much. The tummy was a bit more pronounced and the hair greyer. I still saw her about as she was friends with my step mother, and as the yearly Bar Be Que was that weekend I decided to mention it to her then.

At the BBQ everyone offered me their condolences at the death of Margaret a few months earlier. Molly was sitting on a sun lounger in the garden I sat next to her. She was wearing a green blouse with the top 2 buttons undone and knee length button up cotton floral skirt.

"Hey Molly, how's it going?" I asked.

She looked me up and down and replied "I hear you need a job, what have you got in mind?"

"Same as 10 or so years ago." I countered.

"Really, do you need my help arranging clients again?" she asked with obvious excitement...

"Same Arrangement as before," I queried.

"Well, I'm free tomorrow night to discuss terms and for a trial run." She offered.

"See you at yours, 7PM?" I asked.

"Make it 6, I need to make sure you are still in full working order and will work you hard." She said.

I had kept up going to the gym so had maintained my muscular physique, though now had a bit of grey around the temples, I said to her "Do you think you'll be able to handle it, now you are older?" I countered.

"I bought a dildo that was about the size of you when you left the business, so we'll see." she said.

With that I kissed her on the cheek and stroked her thigh through her skirt, she sighed and said "If you keep doing that I'll shag you here and now."

I held her hand in my other hand and dared her "Go on then."

She looked around and saw by now that everyone else had gone in side, just then my mum shouted from the door way "Are you 2 alright out there?"

"Fine thanks Mum, we are just talking." I replied.

She could only see our backs from the doorway so I continued stroking Molly's thigh. Molly opened her legs slightly so I could stroke the inside of her thigh.

"I'm just catching up with Nick." she said to my mum as my hand stroked closer and closer to the top of her thigh.

"Can you come in now though? I can lock the back doors then" said mum.

Reluctantly I stopped stroking her thigh and we walked back in with Molly looping her arm inside mine. As I hadn't really drunk that much I offered to drive Molly home, she smiled and accepted thanking my mum for having such a considerate son.

As I drove Molly home we chatted about how nothing in particular, we pulled up outside her house, she asked me in for a coffee, and Molly closed the front door after me and locked it. She started to walk into the kitchen, I walked behind her and put my arms around her and started mauling her tits through her blouse.

She pushed her bum back into me and "I wanted your hands on me all evening." I released my grip slightly and she kissed me hard, I ripped her blouse off sending buttons everywhere, she grunted her approval, I then grabbed her skirt and ripped that off her as well, leaving her in a non matching set of sensible underwear.

"I didn't expect to get shagged tonight." she said.

She took my hand and led me to her bedroom, "We'll have to be quiet." she whispered as we were half way up the stairs, "I've got a lodger now, Miriam is in the spare bedroom asleep."

We went into her room and closed the door, she pulled my shirt off me and lowered my trousers to the floor, I had gone commando and she expressed her delight by kneeling in front of me and sucking my cock into her mouth.

"Jesus!" I exclaimed.

She released her grip on my cock and said "Shush," before taking it back in.

Soon I was ready to cum and tapped her on the head; she just grabbed my arse cheeks and held me in place until I exploded into her mouth. She swallowed it all and wiped her mouth when the back of her hand, "Delicious, now lick me out," she said.

She lay down on her back on the bed, I lifted her bum cheeks and removed her white knickers, and I then dived between her legs and sucked her pussy lips into my mouth.

"Fuck," she said.

"Shush," I said briefly removing my mouth.

I then located her clit and started licking that, soon she was going to cum, she grabbed the edge of the duvet and put it in her mouth and bit down as she came, she shook for a good 30 seconds before she calmed down.

I removed my mouth and climbed up her body, as I did that she removed her bra just before I sucked one of her nipples into her mouth, she started to pant as I stuck a finger into her now wet pussy, followed by another one, and the proceeded to finger fuck her to another orgasm.

"Give me a minute." she said.

I moved up the bed and I laid on my back next to her, she rolled over and placed her head on my shoulder stroking my chest, 2 minutes later she threw a leg over me and straddled me, she grabbed my now erect cock and held it as she dropped her weight onto me, taking me in one smooth motion, she grunted as I hit rock bottom, she then started to ride me, soon she was started to pant and came with a scream as my pubic hair stimulated her clit.

I rolled us over so I was on top, and then started to hammer away in her, this seemed to cause her 1 big long continuous orgasm, she was whimpering and scratching my back as I pounded her, I was now ready to come again and warned her.

"Where do you want it?" I roared.

"In my fucking slutty pussy." she answered.

I then shot my load inside her which caused her to scream.

"Give it all to Me." she screamed.

As we calmed down and I pulled my cock from her sopping pussy above the noise of her panting I could hear a buzzing noise. "What's that?" I asked.

"Miriam and her vibrator I guess," said Molly.

"So much for being quiet," I said.

We fell asleep in each others arms and I woke up at 3 in the morning needing a wee, I disentangled myself from Molly's arms and legs and run to the toilet and went.

After washing my hands I opened the bathroom door to be confronted by a short, slightly chubby lady, she looked to be in her mid 40's with permed brown hair in a hair net, wearing a thin dressing gown and what looks like a silky night dress on underneath. She also had a big scowl on her face and can of mace in her hand.

I put my hands up and said "You must be Miriam."

"MOLLY, Call the police," she shouted, "There is a naked man in your house!!"

Molly shouted, "Don't worry, it's only Nick, send him back in here, I haven't finished with him yet."

Miriam looked offended and said "oh well, erm yes, well."

I gave her a quick salute and walked back into Molly's bedroom.

I gave her 2 more orgasm with my tongue and another 2 with my cock before I left at about 5 in the morning.

At about noon my mobile rang it was Molly.

"Morning sexy, Well you passed your test and I have some clients setup," she said.

"I mentioned you were back in the business to a few ladies at the coffee morning and Mrs Harford wants to see you at 2 this afternoon, her husband is out playing golf. She seemed very keen to see you again."

"Ok, did you chat to Miriam?" I replied.

She just laughed and said "I've told her you'll be staying over once a week, and it could get quite loud, if she doesn't like it, she can find somewhere else to live."

At 2 on the dot I arrived at Mrs Harford's house, she was dressed in what I swear was the same dress she had on when I saw her last nearly 10 years ago, she ushered me in and showed me into the lounge and asked me to sit on the sofa.

She sat next to me and said "I've been on a diet, and lost nearly a stone."

She started to undo the buttons on her dress starting from the top.

I kissed her gently on the corner of her mouth and said "No rush, my first 2 hours for old customers is free."

She smiled and said "Let's go to bed then, my husband is due home at about 5."

I remembered that Mrs Harford liked being fucked whilst wearing her dress, something about being naughty whilst looking prim and proper.

I was led by the hand to her bedroom where she shut the door and locked it.

"No escape now." she said.

"Why would I want to?" I replied as I took her in my arms and kissed her thoroughly.

I laid her on the bed and next to her and we spent the next 10 minutes kissing and she removed my shirt, I moved down the bed and crawled between her legs under her dress, I kissed her thighs as I went, I reached her knickers and pulled the gusset to one side, and stuck a tongue into her slit.

"Be gentle, you are the last person who ever made love to me." She said.

I licked her slit and she came immediately, I kept licking her even though her hips were bucking and it caused her dress to rip where I was between the front and back of it, I kept licking and 2 minutes late she came again, this time she grabbed me head through the dress material forcing my nose into her cunt, All I could smell was rampant woman.

She let me go and I crawled out from I under the dress pulling her knickers down with me which she found funny. She hitched her dress up so it was above her waist, I removed my trousers and underwear and then laid on top of her, she grabbed my cock and placed it at her entrance, she rubbed it up and down her slit to make it all wet.

"Are you ready?" I said.

"Do it" she replied, I slowly entered her, the head popped in and she screamed, I removed it and went back in again, this time a little it further, she was tight, it took 10 minutes of slowly moving back and forward for me to hit bottom, she wrapped her arms around me and held me tight. I then started to move my hips slowly and she started doing the same, she soon loosened up and soon we were fucking.

"Rip my dress off," she panted.

"Are you sure? I asked.

"Who's the client?" she said.

I stopped fucking her and grabbed the dress at the top and pulled, the dress tore down the middle and opened so she had both her arms in, but the body and skirt were now open. I removed my self from her and turned her over, I pulled the dress from the back removing her arms from it, and then threw it on the floor, I then removed her bra and then re-entered her from behind, she was now naked and saying some very unladylike things as I vigorously fucked her.

"Wear my dress will you?" she said.

Now this was a new one on me but I removed myself, found the dress and put me arms through the arm holes, I had to rip it to get in on.

"Lay on your back." she said.

I lay on my back as she straddled me and started to fuck me.

"I've always wanted someone to wear my clothes whist fucking Me." she said through her panting. .

She screwed me harder and harder, she came twice and then I announced I was close.

She got off me and stuck my plum head in her mouth, I exploded in her mouth and she couldn't swallow it all, it run down her chin. She licked at her chin with her tongue and then run into the bathroom, she came back in a couple of minutes having washed her face and cleaned her teeth.

I had removed her torn dress used it clean my cock and threw it on the floor and was laying on top of the bed stark naked, she smiled and lay next to me stroking my arms and then kissed me hard on the lips.

"Thank you so much, I always wanted to try something so kinky, but never had the courage, you don't judge me and let me do anything," she said.

"My only rules are no pissing or shitting and nothing up my arse," I replied, "Anything else goes. By the way you still have half an hour free."

Just then we heard a car pull up outside, she wandered over to the window, "Shit it's my husband," she said.

"Not a fucking gain," I said.

"Stay there, until I come for you" she said, she leaned over and kissed me before finding a sleeveless knee length, pin stripe front zip up dress from the wardrobe and putting it on, the zip went from the top to bottom, she didn't put on any underwear in her haste, she checked her hair to make sure it looked reasonable and went downstairs.

"You're home early," I heard her say.

"No shit Sherlock," I thought.

"What's with you?" he said, "Your hair looks a mess and your face is bright red."

"I've been up in the loft." she replied,

"Oh OK, I'm going to watch TV for a bit in the lounge." he said.

I heard her move around downstairs and then heard the kettle being boiled and then heard her say "Here's your tea dear."

I heard him mumble something and then heard her come up the stairs; she went to the toilet and then stuck her head in the bedroom.

"He'll be asleep soon, you can sneak out then." she said. I heard go back down stairs and then immediately come back up stairs.

She came back into the bedroom and stood next to the bed and said "He's asleep, you had better go."

"Is he a deep sleeper?" I asked.

"As he has had a few, then yes," she replied.

"Good," I said,

I grabbed her hand pulled her onto the bed and kissed her, as I kissed her I started to unzip the dress from the top.

She pushed me off saying "He may wake up and wonder where I am."

I rolled on top of her and continued unzipping the dress. When completely unzipped I opened it and kissed her naked breast.

"We can't, he's down stairs," she said, and then "Jesus that's nice," when I sucked her nipple into my mouth. I then started to rub her slit which was still wet.

"Quickly then", she said as she spread her legs wide. I placed my cock at her entrance and plunged in. she put her legs around my waist and started pushing back at me as I ploughed in and out of her, she started to scream in orgasm so I put my hand in her mouth.

The riskiness and rudeness of the possibility of being caught seemed to spur us both on as I came inside her, triggering another orgasm from her.

We quickly got dressed and she let me out of the front door with peck on the cheek and a pat on the arse.

The next day Molly had lined me up with a new client, her name was Donna and she was the leader of the local Women's Institute, a very proper and respectable organisation that is more well know for tea and cake than sex.

Donna was mid 40's and quite large. Over 6ft tall and a UK size 18, she had large hips and thighs and a large pair of breasts. She also had a permanent scowl on her face. Her husband was the owner of the local night club and was know locally as being very large with a short temper.

I met her at the WI hall after their meeting and proceeded to shag her in arse and pussy, and then finishing off by spraying my load over her large tits. She didn't have a scowl on her face anymore when I had finished.

Later the same day I was to meet another new client called Michelle.

Michelle was going to be celebrating her 50th birthday next week but wanted an early birthday present to her self. She was going to be an overnighter at a hotel in a nearby town; I arrived at the hotel and waited in reception wearing my suit and with the requisite red carnation in my button hole. I had reserved the room in my name so her husband wouldn't know, so had already left my overnight bag in there after checking in.

A lady approached me and said "You must be Nick, I'm Michelle."

I looked at her, she was the polar opposite of Donna, she was just over 5 ft tall and very slim, she had one a trouser suit, the trousers were flared but the jacket was tight, it didn't look like she had anything on under the jacket. She had dark wavy hair and her smile lit up the whole room, her eyes were blue and sparkled.

"Hello Michelle, well let me say how gorgeous you look." I said,

She giggled and whispered "You are being paid to say nice things to me."

"Maybe but it's all true." I said and led her into the hotel bar; we had a drink then a lovely meal.

She paid on her company credit card saying "They think I'm meeting a potential client so they expect me to ply you with drink and food."

"Thank you your company." I said, she then reached into her overnight bag and passed me an envelope, and said "I managed to get your fee from petty cash," she giggled, "They think I'm taking you clubbing."

I smiled and gently held her hand. "Would you like to go to bed now?" I asked.

"Yes," she said.

We walked to the lift and arm in arm, we got into the lift and stood at the back as we the lift filled up, I pulled me arm and free and moved my hand to her bum and gently started to feel her tight bum. She pushed back, the lift then cleared at the 2nd floor and I continued to feel her bum, she just sighed.

The door opened on the 4th floor and we walked to the room, I unlocked it and she walked in, and I followed.

"Can you please put the Do Not Disturb sign out before locking the door?" she asked.

I smiled and did as I was asked.

I locked the door and hung my jacket on a hanger in the wardrobe.

She had walked into the bathroom carrying her bag and shut the door, "I'll be out in a minute," she called out from the bathroom.

I lay on the bed and waited for her to return, a couple of minutes later out she walked.

"Fuck me," I said.

"That's my plan," she said.

She was wearing a bright ted teddy with a red thong and nothing else. Her small but perfectly formed breasts sat perfectly pert on her petite frame. Her legs were slim and blemish free and she looked good enough to eat.

"My husband only likes sex, in the missionary position, under the duvet with the lights out," she said. "Can we do more, I've seen some things on the internet I'd like to try," she continued.

"We can do whatever you want, as long as nothing goes up my arse," I said.

She skipped and clapped and then walked over and took my hand; she asked me to stand and then said "Can I undress you please?"

"Of course," she then started to unbutton my shirt, she pulled it off me and threw it on the floor, she then pulled trousers down taking my socks and shoes off at the same time, and she rubbed my now erect cock through my boxers.

She pulled my boxers down and gasped, "It is true!"

The boxers were swiftly disposed off and she pushed me onto the bed and landed on top of me, we then started to passionately kiss as I rubbed her back and arse, I run a finger down her arse crack which seemed to make her kiss me even harder.

She pulled herself up and lifted the teddy over her head and threw it on the floor.

She then resumed kissing me; she then leant back and started to play with my cock.

"Can I suck it please?" she asked.

"This evening is about what you want," I said.

She moved down and sucked the head into her mouth, she was the best cocksucker I ever met, she got most of it into her mouth and her mouth was like a Dyson. Soon I was ready to come and told her.

"Do it," she said took me nearly all the way in, and what felt like half way down her throat. I came with a roar, she swallowed the lot.