Gigolo Ch 03

“How did the job hunting go, Allen?” asked my mother after I had returned home from escaping the clutches of the randy Lucia.

“Actually, I think I may have found a situation that suits me perfectly, Miranda,” I replied. I had been calling her by her first name ever since I turned 21. “It’s a bit early to be certain but it really does look promising. In fact, I got a $2000 advance. How about we go to Luigi’s for a spot of italian to celebrate.”

Not long after, we enjoyed some of Luigi’s pasta and a couple of bottles of superb Chianti. I watched as my gorgeous mother fended off Luigi’s lame attempts to inveigle her into his clutches. Mind you, I didn’t blame him a bit. Tall, stylish, chic like Jaqueline but a few years older. Beautiful face, brown eyes and dark wavy hair. As always, I perved at her deepish cleavage when I thought she wasn’t looking.

“That Luigi, he never stops,” I bantered.

“Yeah. Funny thing is that he knows Mrs. Luigi is waiting in the kitchen with a big sharp knife if he even looked like succeeding. Tell me more about this job.”

Walking to the restaurant I had decided not to tell the truth. No real reason. I doubted Miranda would be upset apart from a few “be careful”s thrown in. I pretended that I was in direct marketing a range of products and mentioned a few of Jaqueline’s products. In fact, I intimated she was my boss and embellished from there.

My mobile rang halfway through the second bottle of Chianti. It was Mrs. Croker from Discreet Gentlemen Escorts, my employer.

“Interupt anything interesting, Allen?”

“Nope - dinner with my mother, and very pleasant it is too,” I responded smiling at Miranda.

No beating around the bush. “Tomorrow. 4pm - Misty Valley Flower Shop. You know it?”

“Yep.”

“OK. Remember, you have to come into the office Friday afternoons for settlement.” And I knew what that meant.

We finished our meal, and staggered back home, arm in arm, slurring the words to “Oh Sol Oh Mio”. Went out like a light and slept ‘til noon the next day. Pottered around, visited the hair stylist, bought some new shirts and presented myself at the flower shop at the due time.

“Allen?” She had to be 60, snow white hair, chubby pink cheeks, and twinkling gray eyes. Her figure was like a snowman but with equal halves.

I acknowledged that I was indeed Allen, wondering what the assignation was all about. Somebody in their 60s would be a novel experience.

She must have caught some type of interest in my eyes. “You’re not here for me, young man,” and her eyes crinkled merrily, as if the idea amused her hugely. “You are here for my daughter Dorothy. I’ve hired you to take her to a reunion dinner dance at her old school.” She frowned. “Dorothy has let herself go in recent years and really doesn’t want to go. However, I’ve been prevailed upon by two of her old girlfriends to find a way to get her to go. You are going to pretend that you are her current - er stud muffin?? Is that what young kept men are called?”

“I really don’t know. How old is Dorothy?”

“Very nearly 40 and resigned to spinsterhood. I’ll take you up and you can meet her. If you can persuade her to dress up a bit, I will provide you with a bonus, plus another if she enjoys herself. What do you say?”

“A challenge is a challenge. Lead on MacDuff.”

“Betty.”

“Right - lead on Betty MacDuff!” She giggled uncontrollably as I followed her to the flat upstairs to meet the challenge.

Good grief! A challenge - what an understatement! She was slightly taller than her mother and dressed in a dowdy old caftan that did a great job hiding any of her physical attributes. She wore glasses with round black frames that did nothing for her. Her hair was dark and straggly with gray wisps. Her big brown eyes were intelligent and vexed. Behind her was a desk covered with dusty tomes and a PC showing an archaology site.

“Mother, I told you - I’m not going. Just send this young man away and pay him for his trouble.”

“Now Dorothy, you promised me you would make an effort. At least let Allen try.”

Dorothy scanned me up and down and sniffed. “He’s very young. Too young to know what to do.”

Her mother looked at me pleadingly. I reacted to those lovely eyes, and hoped I wouldn’t regret it. “Dorothy, I may be young but I am mature. No mucking about. Let’s go. You and I have some shopping to do and we have no time.”

Startled by my no nonsense tone that probably reminded her of her daddy, she shuffled toward me. “You are doomed to failure, Allen,” she murmured with downcast eyes.

I drove her to the nearest huge mall and cajoled a hair stylist with a wad of money to attempt to give Dorothy a makeover including makeup, nails etc. I sat and watched a transformation take place. Sylvie the stylist had ascertained that Dorothy had contacts and had made her put them on. With makeup highlighting them, her big brown eyes became most attractive. The hairdo was inspiring to say the least, taming and shaping with some judicious cutting into a style that framed her rather cute face. She smiled at the result and the dimples on her cheeks were charming indeed. Next the dress.

I took her into an upmarket shop that was thankfully uncrowded. Dorothy was far from enthusiastic. Looking around she exclaimed that there was nothing there that would suit her. I wasn’t so sure. I pushed her into a cubicle and told her to get out of the shapeless kaftan and I would bring her a selection to try on. I waited until I was sure she was out of it and then pushed the door open and shut it behind me. She held the kaftan in front of her and looked at me alarmed. I pulled it away from her and threw it over the door. She tried to cover up but I pulled her up straight and demanded she stand still while I checked her for size. She straightened up and I was amazed to find a voluptuously hour glassed figure. Big, big tits filled almost all of what I took to be a maternity bra. Her knickers were white and plain. I spun her about and grabbed the tab - it read 44GG. While at it I noticed that her back was smooth, creamy and shapely, curving in at the waist and flaring out over wide child bearing hips. I had expected her legs to be thick and raddled with cellulite. They were strong looking and unblemished. She actually had quite a sexy body.

I went out into the store and quickly got the attendant on side. I got four sets of sexy, lacy bra and pants sets with the bra measuring 40DD ensuring they plunged at the front. One set was dark blue, another light blue, the third was red and the last, black. Returning to the cubicle, I told her to get rid of her underwear and put the red set on. She actually looked at what I was holding with some curiosity. I left to get her an assortment of clothes from a couple of smart suits to a couple of slinky evening gowns with plunging necklines - one red to match the underwear and one in midnight blue. I figured strong colours would compliment her dark colouring.

I returned to the cubicle and found her wearing the red set but facing the corner. In no mood to fuck about, I pulled her around. Her huge breasts were bulging out of the bra creating a marvellous cleavage. “I can’t wear these,” she whispered. “I just can’t. Don’t make me. Please.”

“You look absolutely fucking gorgeous, Dorothy. Truly fuckable. I’d root you right now, my girl, if we didn’t have so much to do and no time to do it. Now shimmy into this red number and stop protesting,” I growled. She glared and me and I at her. She raised her chin and almost defiantly pulled the red dress from me. Ascertaining her shoe size, I left to pick up some evening, daytime and business shoes. When I returned, she was dressed and it fitted her like a glove. It wasn’t too tight but it showed off her voluptuous figure to perfection, her impressive cleavage on show.

She was turning around looking in the front and side mirrors. I knelt and slipped her quite shapely feet into two inch heels that firmed up her calves and added shape. I’d outdone myself, she was actually very attractive. I got her to try on the rest of the items I had picked and she was happy with the lot. She paid by credit card and we left with her still in the red outfit. I had included a black evening cloak that kept the chill and the stares from her.

Her mother was stunned and stood there gaping, her arms full of flowers. She nearly dropped them when I pulled the cloak apart to reveal Dorothy’s glorious assets. “Good grief, Allen. Who is this? What have you done?? She looks wonderful.”

“We don’t have time, Betty. We really have to go.” I ushered Dorothy out and drove her to the reunion.

On the way, she twisted her hands nervously. “I’m not sure about this Allen, I feel like a tart. I’m afraid of what my old friends are going to make of this outfit. You will stay close, won’t you?”

I assured her I would and presently we arrived and decamped into a crowded decorated gym hall that had a band playing on the stage at one end. I removed the cloak despite her clutching fingers and placing her my hand firmly beneath her arm, we forth to meet and mingle. Within minutes, a couple of mid aged women had rushed up. “Dorothy, is that you?” one exclaimed. Both women were dressed comparatively conservatively and both were married. They introduced their husbands whose eyes were drawn to the cleavage on show. One was heard to mutter to his spouse something about being told that Dorothy was an old maid, and if what was in front of him was an old maid, he’d eat his hat. Other males arrived like bees to honey and she was whisked away for a number of dances. I saw a few of them clutch her to them, surreptiously copping a feel of her big firm and shapely arse. In between dances, I plied her with wine and watched her cheeks become flushed and her eyes sparkle.

Some of her female classmates drifted my way and I danced with a couple who managed to cop a feel of my tackle and whisper that they would like to show me their old classroom. I gracefully declined. After all, they hadn’t paid for the privilege. Eventually, I claimed Dorothy for a dance and she melted against me sighing.

“Oh Allen, this has been a wonderful evening. I feel like the belle of the ball.” She looked up at me. “Some of the guys were trying to get me outside.” She giggled, half pissed. “I told them my resident stud might not like that. You wouldn’t would you?” I smiled at her and nodded, pressing a kiss to her dampish forehead. She sighed and snuggled her curvy body against mine. My cock tingled and I decided it was time to leave. We left amid a plethora of requests to meet soon and drove to her place.

Betty was waiting up and took one look at her obviously happy daughter and beamed at me. “Mission accomplished, Allen. I’ve never seen her so happy. I’ll put her to bed and we’ll settle up.”

“I want Allen to put me to bed mother,” Dorothy demanded, and grabbing my arm, pulled me past her gape mouthed mother and up the stairs. In her bedroom, that could also have done with a makeover, she stood against the bed, arms akimbo. “I want this night to end as beautifully as the evening has been. I have almost no experience but I want you to make love to me, to fu.. to fu.. to fuck me! That is, unless you don’t find me attractive. At the shop, you said you would roo... er what was it?”

“Trust me girl, you are eminently fuckable. And I do, very much.” I pulled her close and kissed her gently at first then demanding, forcing my tongue into hermouth and duelling with hers. I pulled the zip of her dress down while moving to kiss the hollows of her neck and then slid the gown off her shoulders and down over her out thrust breasts to pool at her feet. I slid my palms over her lace covered mounds, feeling sizeable nipples erect at my touch. I quickly unclipped the middle and peeled the bra cups off. Big, big, white and creamy with a tracery of blue veins, acorn sized nipples standing proud from perfectly symmetrical coral pink areolae. I swooped on them like a ravenous dog - sucking, slurping, biting, nipping, licking until they were rigid. So was I.

I flung my clothes off except for my bulging briefs and sat on the edge of her bed. I pulled her between my knees and kissed my way down her tummy, swirling the tip in her belly button. Wisps of pubic hair had escaped each side of her sexy panties and I drew them down and pushed them to her feet. Her shaggy hairy pubic mound could have done with some trimming but I could live with it. I parted the folds of her vulva as she clutched at my shoulders. I gazed in rapture at her pink insides and pushed my tongue between her lips and began to fuck her with it. I slid up and sucked her bulging clit while slipping a finger into her tight cunt.

She was clutching and shuddering, moaning, “oh Allen, oh, oh, oh Allen,” while she tweaked her nipples. She came and suddenly sank to her knees in front of me. My cock was standing upright and she grabbed it hard and kissed it’s glistening helmet. She looked up at me like a naughty school girl. “I’ve never done this but I want to. Don’t stop me.” She kissed it all the way down to my balls and then up again to take the knob into her hot mouth to begin to suck. She certainly was no expert, but I coached by words and murmurs and finally, at my urging, wrapped her huge tits around my shaft and rubbed them up and down while still sucking. Without warning, I erupted into her gobbling mouth and, after only a split second of hesitation, she swallowed the lot and licked the rest of the escaped pearly fluid. Dorothy looked up at me with a smile and said, “I rather liked that. I liked the feeling of control. I liked the feeling of making you spurt like that, and I loved the taste. Can we fuck now?”

After a small bit of enjoyable foreplay, I lay on my back as she slid her tight, tight pussy down my rigid shaft until it bottomed out. She then rode me while I tried to control her massive tits, reaching up to lick and bite while giving her now pulsing clit a series of massages that sent her off orgasming mightily, moaning and issuing little shrieks as she did. As I felt her begin to tire after a major then a series of minor, orgasms, I pushed her onto her knees and shafted her from the rear until I spurted deep within her. We toppled over and fell into a spoon position and went to sleep, my slowly deflating prick esconced within her still pulsing cunt.

Next morning, I slipped out of her room leaving her sleeping like a baby. Betty met me at the bottom of the stairs and pressed a bulging envelope into my hands. “Allen, that was the most amazing transformation I could have ever imagined. I don’t know how to thank you. I heard her enjoying herself as I’d never hoped I would. She is an extremely respected archaeologist and has never had the time or inclination to do anything like that. You are a miracle worker.” She reached up and bussed me on the cheek. “Lucky, lucky girl.”