"Howdy!!! We over slept! We need to be at my lawyer's office in an hour. Get up!"
"What?" I said rubbing sleep from my eyes.
Gypsy and I sprang from the bed and raced into the shower together. It was just a quick suds up wash off, but it would have to do. Nothing cologne and perfume can't hide Gypsy said with a giggle. We quickly dressed, and made a mad dash for the appointment. "We are signing papers today to make our business official." she said out loud, talking to herself. "Thislawyer charges more per hour than you do Howdy." Gypsy mused, forcing a laugh. "We can't afford be late."
We slipped into traffic for the short ride downtown. "Ok Gypsy." picking up the conversation again, "you know I trust you 110%,and if you think we need an legally binding contract, then we will do contract. I just want you to be happy!" I said, rubbing the back of my fingers against her cheek.
As I followed her directions towards his office, Gypsy still seemed a bit on edge, "I know Howdy, but we need to set this up right, and should have done it a week ago when we started. I don't like loose ends. Loose ends make me nervous. That's all."
As I drove, she calmed down a bit and then slowly ran her hand up and down my thigh. "I'm sorry for making this a stressful morning Howdy. Some day you will see the importance of what we did today."
We pulled into Smith Towers downtown and found a spot near the front doors. Gypsy and I had both worn suits and looked the part of true business professionals. Well, at least she did. I felt like a clown all dressed up like this. But there wasn't anything I wouldn't do to please Gypsy, so I dressed up.
I had to quicken my pace to keep up with her brisk stride. She seemed unusually focused and very determined. I had never seen this serious side of Gypsy before.
As we neared the lawyer's office door, Gypsy realized we had made it with several minutes to spare. She looked at me and took a deep breath, then finally gave me that classic sultry Gypsy smile. We stepped inside and told the receptionist who we were to see.
She placed a quick call and said, "Mr. Jamail will see you now."
"Gypsy! How are you my dear?" the lawyer said, giving her a warm embrace and a peck on her cheek. "You look stunning as always."
"Mr. Jamail , I want you to meet a very special young man. He and I are partners in the new venture I told you about."
Suddenly, I felt awkward and embarrassed at being introduced to one of her very prominent friends. If Gypsy told him everything, then he knows what I do. I felt dirty, diminished in some odd way.
"Very nice to meet you young man!" he said. Gypsy tells me you do all of the heavy lifting so to speak and she just gets to count the money. Is that true?" heteased with a wink and a laugh. "So Howdy, do you like being in the service industry?"
I stammered and before I could answer, Gypsy rescued me, "Mr. Jamail, Howdy is a natural when it comes to selling the home services we offer. He far exceeds customer expectations and has yet to not deliver as promised. In fact, not a single complaint. All I get are rave reviews and requests for more. What more could we ask for?"
"Howdy, you keep this woman happy and stay on her good side, and she will make a huge success out of you." he said, offering some fatherly advice.
"Let's see all your papers Gypsy. I want to make sure we have all your bases covered."
He pushed his glasses to the end of his nose, and with raised eyebrows, mumbled 'ah ha', and a few 'hmmms', and muttered some 'oks' repeatedly as he read carefully through the papers.
Then giving a long stare first at Gypsy, then at me and then back at her, he pulled his glasses off, holding them in one hand as he twirled them,
He slowly leaned his head back as he peered at us with a perplexed expression, "Gypsy, forgive me for questioning your wishes. Are you absolutely positive you want these directions followed to the 'T'? You know, everything executed exactly as you have so precisely outlined here?"
"Absolutely 100% sure Sir." Gypsy answered with a big confident smile. "Howdy is my partner and I want him to be a part of everything I do."
"Very well then. I'll have all the contract drawn up as you outlined and then call you in a few days to come back and sign them in front of witnesses. Check with my assistant for the first available time next week."
We stood in unison, and he turned to me and took my hand, shaking it slowly. Then with a puzzled smile, he added, "Howdy, you have no idea how lucky of a guy you are. I'm sure we will be seeing each other again."
Gypsy and I walked outside. She stopped, looked around as if suddenly realizing the sun had come up. She smiled and took a deep breath before looking at me.
"Why are you looking at me that way?" she asked as we stood smiling at each other.
I gave her a boyish shrug of the shoulders and we both laughed.
"Now I can breath easier." Gypsy said with a big sigh. "I could just eat you up right here on the street." she teased. "Howdy, I'm hungry."
"Want Chinese" I asked?
"Are you thinking Kim Son?" she asked licking her lips. "You know Chinese makes me hornier than hell Howdy. Are you sure you can handle me? Hmmm?"
"I had no idea Chinese food had that affect on you Gypsy." I said returning her wink. "Then Chinese it is!"
During lunch, Gypsy told me she had only booked one appointment for the afternoon because she wasn't sure how long it would take at the lawyers offices. "Your appointment is at 4 o'clock Howdy. That should give us plenty of time to eat and get home, maybe even relax a bit.
As we sat eating, I told her how funny I felt when we first talked about my role in the company in front of the lawyer. Then I thanked her for tossing me the proverbial life preserver.
"Sooooo, I sell home services eh?" I laughed hard.
"Howdy, Mr. Jamail has no idea what services you provide. I interrupted so you wouldn't inadvertently spill the beans on our harmless lil prostitution ring." she said with a wink.
"Ahhhh, I see. I never really thought of myself as a hooker, but hey, it's fun and it's bringing home some cash." I laughed.
We finished a light meal and headed home. Gypsy couldn't wait to get home to get comfortable and started shedding clothes as we entered the freeway on ramp. Soon, all she had on was her underwear and heels.
"You are quite a sight Gypsy." I said, taking my eyes off the road long enough to admire her lovely semi naked body.
"Thank you baby!" she said as she hit the recline button on her car seat. One thing I enjoyed about driving Gypsy's El Dorado, was the fact that it was convertible. She hadher seat nearly totally horizontal and decided that if her car was going topless, she would too.
"I'm gonna tan my tits for a few baby." she said as she gave them both a nice squeeze. I reached over and rubbed at her flesh as she squirmed in the seat. She took my hand and slid it between her legs. Her warm soft pussy hair felt like silk as I rubbed her shear panties across her swollen lips. Gypsy took hold of my wrist, holding my hand in place over her warm cunt as she forced her wet panties against my fingers. Then she reached across the large front seat and rubbed the growing bulge in my pants.
"Howdy," Gypsy's face lit up with a very naughty smile. "have you ever had a blow job while you were driving?"
"Uh, nooooo. Why? Are you taking me on my maiden voyage today?" I laughed.
It was bad enough that her big ass red car demanded attention on it's own. Now I was going to have this beautiful near naked woman sucking my cock as I drove down the Gulf Freeway towards Galveston.
Gypsy played with my bulge through my pants, telling me exactly how she was going to suck me off. Between playful nibbles and tongue probes to my ear, she whispered every last naughty detail as she moved close to me, hand still rubbing my throbbing member. Then she unzipped me and pulled my cock through the opening.
"Oh my Howdy. It looks like you just might like this voyage." she purred.
The next thing I knew, she was on her knees in the front seat with ass in the air for all fellow motorists to enjoy. Gypsy had my cock in her mouth and was sucking and pumping for all she was worth. It was a struggle for me to keep my focus on driving the car, instead of driving my cock deeper into her mouth. I reached over her back and pulled at the waistline of her panties, pulling them snugly between her ass cheeks. Then I ran my hands over her cheeks before running my fingers down her wet slit.
A long blare of a pickup horn told me I had strayed too far into the lane next to me. I was sure the driver was going to flip me off or yell at me as he pulled up next to my passenger door. But when the guy saw Gypsy's naked ass wiggling on the end of my fingers and her head bobbing up and down in my lap, he smiled big and gave me the thumbs up. He and his buddy rode next to us for a good two miles before they finally sped off.
"Cum for me baby. Fill my mouth with cum Howdy." Gypsy moaned as she sucked me hard and deep.
She pulled her mouth up my shaft to suck only my head as she pumped me with her hand. "That's it baby. Give it to me!" she grunted excitedly as precum formed on my head.
She took me in her mouth again and gave my balls a gentle squeeze as I unloaded in her waiting mouth. Gypsy gobbled down every drop and stroked me until she was sure I had given her the very last drops of cum I had.
"Hmmmm Howdy. How was your maiden voyage? she giggled, laying her head back in my lap. She held my cock in her hand like it was a souvenir as she curled up in the seat and closed her eyes for a little well deserved cat nap. Gypsy slept like a baby until we got back to her house.
The time to leave for my appointment quickly came. "There's your directions Howdy." Gypsy said with a lazy yawn. "Teresa is a dear friend whose husband left her six months ago for his much younger administrative assistant. The young bimbo wrecked his marriage and then, only a few weeks ago, the bimbo left him for a younger guy. Go figure!" Gypsy chuckled at the twist of fate.
Teresa's home was in the end of a big cul-de-sac. The homes were very nice and quiet large. The web of shadows cast by the ages old Sycamore branches laced the street and front yards. A woman wearing cutoffs, sneakers and a faded denim shirt was on all fours pulling weeds when I pulled up. I sat in my car for a minute admiring her nicely shaped ass wiggle while she worked. The large straw hat she wore hid me from her view until I was nearly to her.
"Hello. Excuse me. I'm looking for Ms. Teresa." I said with an engaging smile.
The woman sat up on her knees, and peered from under the hat half stunned to see me, then looked at her watch.
"Are you Howdy? Is it 4 o'clock already? Oh my. I completely lost track of time." she said apologetically.
"Be a dear and help me up." she laughed at herself as she offered me her hand. "Please forgive me. I get so lost in garden work that I am forever losing all track of time."
"It's ok Ms. Teresa." I reassured her. I have all the time in the world. I can wait, or I can come back another time if you wish." I offered.
"Howdy. You drove all the way out here to see me and today is just fine. Please, come in the house with me. I think we could both use a tall cold drink."
She took a couple of steps towards the house, then she stopped and turned to face me, "And Howdy, please drop the 'Ms' shit." she said with a warm motherly smile. "To you, I am just Teresa."
"Sounds good Teresa." I said as I followed her inside.
I scanned the large ranch style home. Everything was picture perfect. I moved towards the large plate glass window that overlooked a picturesque pool and lush landscaping. "Wow Teresa. That is the most spectacular pool I have ever seen."
"Thank you Howdy." Teresa said as she handed me a drink. "Cheers!" she smiled with a tap to my glass.
Teresa stood shoulder to shoulder next to me, gazing into her custom made slice of heaven.
"When I designed the pool and had it built, I wanted it to be our oasis, our very own 24/7 vacation destination, our secluded romantic paradise. I wanted my own tropical get away where my husband and I could skinny dip day or night, and fuck away our afternoons. Little did I know then, that I would be enjoying this 'paradise' by myself. Sorry fucker." she said as her voice trailed off.
"Do you like to swim Howdy?" Teresa asked, turning her attention back to me.
"Oh, of course. And that pool does look very refreshing and inviting. It's like something from a travel magazine. It's beautiful Teresa. You have created a very romantic setting too I might add."
Teresa took my hand and lead me out onto the large veranda overlooking the pool. The large rock waterfall and lush vegetation made it look and feel like an island escape somewhere in the South Pacific. The landscaping was so plush, you couldn't see a fence anywhere around the yard.
Teresa walked a few steps beyond me towards the pool. I studied her shape as she slowly walked away. She had long salt and pepper hair that reached past her shoulders. Her hair was mostly a gorgeous lustrous white silver color that shimmered in the sunlight. It looked like she worked out by the way her clothes clung to her body. She wore no makeup, but really, as naturally pretty as she was, makeup would have been a wasted effort.
Teresa stood at pool's edge, then bent over and placed her glass on a table. She took off her hat and leaned her head back, shaking the kinks out of her hair as her fingers combed through her long wavy curls. With both hands on her hips, she studied the landscaping as if there might possibly be something that just wasn't quite perfect, that one little something that might be out of place.
Her eyes panned slowly back and forth, admiring her handywork,before she unbuttoned the top two buttons to her shirt and pulled it over her head. Teresa had large pendulous breasts with large hard nipples. She turned slightly to the side to make sure I was watching the show. Then slipping her fingers inside the waistbands of her shorts and panties, she wiggled out of them too. She bent over to grab her shoe laces, giving me aperfect view of her meaty full lips andthick bush from behind. For some reason, I was becoming a real fan of pubic hair. Then kicking her shoes to the side, she stepped out of her clothes. Then she turned and looked at me as she rested her hands on her hips.
"Well? Are you joining me for a skinny dip or just going to stand there and waste a perfectly good hard on?"
I undressed as I walked towards the pool. As I neared Teresa, she turned to fully face me. Then with arms extended to the sides, she fell backwards into the pool. I stood there in just my pants with shirt unbuttoned as I watched her go under.
I quickly undressed and joined her in the pool. I watched her as she took a couple of laps across the pool and back. With my back to the flagstone coping, she swam towards me. Teresa was not a gorgeous woman by any means, but a very earthy and naturally pretty woman. She placed her hands on the decking on either side of me. Then she slowly stood up, exposing her large tits. Her nipples were rock hard and a beautiful light brown in color. She moistened her lips before giving me a short wet kiss.
"Howdy, I love kissing. Do you?"
Teresa looked at me as she took both breasts in her hands and gave them a loving feel. She pinched at her nipples as she felt the tingle between her legs grow. She pushed her body close to mine, my cock pressing hard against her stomach. Then offered me one hard nipple, then the other for my tasting pleasure.
"Howdy. Do you have any idea how boring masturbation becomes?" As her hands tightened their grip on her tits, she closed her eyes half way. "There is only so much pleasure a person's fingers or dildos can bring to themselves ."
Teresa traced the stubble of my two day old beard before leaning into me for a long lingering hot kiss. She was indeed, a damn good kisser. Our tongues explored each other's mouth for several minutes as we worked ourselves up. I was definitely becoming very aroused kissing this woman.
Reaching under the water and between my legs, she took hold of my long thick cock. "Oh my gawwwd. That's what I'm talking about. The real deal."
Teresa gave my cock a few nice long strokes as she smeared her kisses all over my face and neck. "Does this feel as good for you as it does for me Howdy? Hmm?"
I moaned my approval and she gave me a few more tugs before sliding her hand down andcradled my balls. By now, Teresa had snuggled her tits into my side and was rubbing herself on me as she played with my cock and balls. Then she released my balls and slid her hand further under me, pushing her fingertip against my asshole.
"Do you like this Howdy?" she purred as her fingers pushed at my anus in small circles.
"Yes I do Teresa." I answered as my hand slipped between her legs. "Does this feel good?" I asked as my fingers returned the favor and easily parted her swollen lips. They sank palm deep in her.
Teresa let out a moan as her vagina began to tighten around my slow probing fingers. "Oh gaawwd does it feel good Howdy." Teresa growled as she clinched her teeth.
Holding my hand in between her legs, Teresa turned her back to me and pushed her ass firmly against my throbbing cock. It slid easily up and down between her cheeks. I kissed at her neck and ear as she ran her hands up and down my sides and behind my head.
She writhed as her body slowly became consumed by the pounding of my fingers as they flamed her fiery passion. I held both tits in my hands and pinched her nipples and pulled them hard as she squirmed against me. Then as she wiggled, I forced her legs wider with my foot, and slid a hand through her furry mound in rough probing circles. Teresa had a large clit that was extremely sensitive. It didn't take much to have her twisting body grinding all over me.
My fingers parted her lips and once again found the soft wetness she had reserved for this occasion. Her body shook as my fingers slid effortlessly into her love canal, gripping at her from the inside out. Her loud gasp confirmed that I had found her sweet spot. Teresa held my hand firmly in place as my fingers pumped hard in and out of her. I stroked her large clit between each finger thrust. With her hard nub centered between my long thick fingers, I rubbed the sides of her clit as if jacking her off. I reached to brush the silvery mane from her face, then took a handful of her hair in my hand. I gripped it hard as I pulled her head back, arching her back and thrusting her large tits forward. She didn't have the strength or resolve to resist.
Teresa rocked back and forth until she had her first orgasm. She smothered me with wet kisses and soft moans as her body trembled with eager anticipation for more. Then she pulled herself half way out of the water. She bent over the edge, just her legs remained in the pool. Her upper body laid flat on the pool deck and her ass was at my eye level. Teresa reached behind her and pulled at one of her ass cheeks, giving me a great view of her wild silver haired pussy. I swatted her cheek and playfully nibbled between her cheeks. My tongue darted up and down her squirming lower body as she responded vocally to my every lick and probe. It had been a long time since a man had hadhis way with her. She savored the return of probes to her hot cunt that were not those of her own.
I swatted each cheek hard, then squeezed her ass, spreading her cheeks wide, kneading them roughly like dough. She screamed out loud as I took her whole pussy in my mouth, biting it firmly, sucking her full lips into my mouth. Her ass trembled as my fingers spread her lips and my tongue thumped hard against her wet opening. My tongue darted back and forth between her dripping cunt and her tight rosebud. I nibbled at her hard clit as I drank her juices. As I lapped up her sweet nectar, she fingered her ass hard.
With her lower body shaking with excitement, I reached up and took a handful of her hair, lifting her head off the pool deck and arching her back.
"Come here Teresa!" I said with a low raspy snarl as I took control of her.
With a handful of her silvery locks, she slipped back into the water and looked me in the eyes, waiting for my next move. I lifted one of her legs, and wrapped it around my waist, leaving her spread eagle with my cock poking at her crotch. The anticipation of feeling a man's cock pounding her cock starved cunt was becoming unbearable. So close yet so far away. I took my cock mid shaft and rubbed the head back and forth through her fur covered lips. I made sure the tip of my cock paid homage to her throbbing clit. Each time I pushed the head into her clit, she moaned and begged for me to finish what I had started. Teresa wanted to be fucked. For some odd reason, I took delight teasing her, and withholding the ultimate pleasure she craved. We both knew well in advance what the outcome would be. But I controlled the 'when.'
We moved through the water towards the waterfall feature. "Do you like this Teresa?" I asked, knowing she already was submitting herself to me.
I felt boldly empowered knowing I was some punk ass kid who had just taken possession of this very attractive woman nearly three times my age. At this point her cunt was so wanting to be fucked, there wasn't anything she would refuse to do.
I ran my hand up and down the front of her. From her inner thighs to her throat, I made sure she felt my power. She became putty in my hands. Teresa was in such a state of arousal she was struggling to keep some of her control to herself. As I held her gently by the throat, my other hand slipped between her legs, spreading her lips wide as I roughly entered her. She tossed her head back as my fingers fucked hard at her pussy. She gripped my shoulders hard with both hands as I rammed my fingers deep and hard in her until she came again. Her body became a mass of hot flesh in my hands.
Then I pulled her to me, and forced my tongue between her lips as I lifted both her legs. She knew what was coming and squirmed to place her cunt squarely around the tip of my hard cock. Teresa wiggled hard as she slid effortlessly down my shaft. Almost immediately, she came hard, in a hail of profanity. I felt the warm gush of her hot fluids pour over my stomach as her cunt finally got the prize it wanted. Her body shook hard and her legs tightened around my waist in a death grip as she held my cock deep inside her starving walls. Then she lifted herself up and dropped herself back down on me, then again and again. Each thrust of her hips was harder and deeper than the last. Teresa held me tightly as she showered me in kisses while her body became a pleasure palace full of orgasms.
In the middle of her orgasmic bliss, I said in a calm voice, "Get out of the pool Teresa."
She looked at me like I was fucking crazy. But either out of hope we would finish this fuck fest somewhere else, or not knowing what I would do, she obeyed my soft spoken command. My cock stiffened even harder at the authority I had just so skillfully exercised.
She lifted herself off of me and made her way though the water to the steps. I was right behind her to take in the cock hardening view of her pussy from behind as she exited the water. I took her to the large chaise lounge and bent her over it. Kneeling behind her, I spread her cheeks and licked at her sweet honey hole as she played with her clit. Then I told her I was going to fuck her. I told her she was a naughty slut and she didn't deserve the hard fucking she was about to get.
Teresa's knees buckled as my words became music to her ears. I took both hips and guided her pussy onto the tip of my cock. Then I pushed hard, sinking all the way to my balls on the first good push. She cried out as I began to ram her harder, telling her what a nasty slut she was to be fucking such a young guy. It was obvious she loved a good fucking, and the mildly abusive nature of my verbal assault . The more I talked dirty to her, the more she liked it and the harder she fucked and the louder she became.
I rammed her as deep and hard as I could. Feeling my orgasm build, she reached between her legs, grabbing my balls and told me to fuck her nasty cunt hard. Teresa and I both came in an explosive frenzy of hot spewing fluids. I held her hips tight and felt my cum splatter deep in her pussy as she grunted like a wounded animal.
Teresa fell to her elbows on the chaise lounge and my cock literally made a loud 'pop' as it slide out of her furry love tunnel. A rich mix of hot sticky cum oozed freely from her, forming a creamy puddle on the cushion. Teresa moaned again as I unexpectedly slipped three fingers inside her honey hole, extracting a glob of our sweet treat. Then I smeared the hot mix of our gooey cocktail on her lips and she eagerly accepted my creamy gift, licking her lips and sucking my fingers clean.
Teresa rolled over on her back and grabbed the backs of both knees, pulling them flush against her tits. Cum poured freely from her pussy as the pressure expelled the hot mix. It dripped a long creamy trail down between her ass cheeks. Then Teresa used two fingers to lube her asshole good, pushing the slimy goo finger deep.
"Fuck my ass Howdy! Fuck it real hard." Teresa panted, holding her cheeks wide.
My cock eagerly answered the call. I straddled her ass cheeks, my cock in hand. I rubbed the head through the slippery mess that oozed from her dripping pussy and pressed it firmly against her tightly puckered bunghole.
I gave her outer circle a gently nudge and I slipped part way in. Then as her hips began to move, she pushed hard, taking me past the tight rings as they too surrendered to my gentle assault.
"Fuck me like I'm a nasty whore!" Teresa begged as her lower body came alive again. She pumped her tight ass on my cock as she and I took turns playing with her pussy and tits. Teresa had saved her hardest orgasm for last as she gave the last of what she had reserved for this final surrender. In an uncontrollable body shaking trembler, and amid profane laced utterances, Teresa erupted in a spraying gush. She squirted like a small fountain.
She laid breathing heavily as she played with her nipples and rocked back and forth slowly on my cock. Then she reached up to pull me into her for more hot kissing as she wrapped her legs around my waist. We kissed like old lovers for a long time.
Teresa looked at me and with a bit of anger mixed sadness told me that what we just shared was all she ever wanted from her husband.
"Stupid fucker." Teresa lamented again, shaking her head.
"Guess what Howdy," she smiled broadly, suddenly changing moods, "now you get to play 'hubby for a day' every week for the rest of the summer."
We got back in the pool and played for a bit longer before calling it an evening. Teresa wrapped herself in a long white terry cloth robe and we walked towards the front door. As we neared the door, she reached inside the pocket and pulled out a fairly fat sealed envelope. She swatted my ass with it before handing it to me.
As we stood facing each other, Teresa opened the robe and wrapped it around me, pressing her naked flesh close to me for one more hot embrace.
With her arms wrapped around my waist and both hands full of my ass cheeks, she pulled me firmly into her. She looked up at me, then said with a wistful grin, "Howdy, I know you had fun taking control of me like you did. Don't get me wrong. It was fun for sure, but, next time..."
She bit her lower lip as her eyes narrowed, and a mischeivious smile crept across her face, "Well, let's just see what happens next time."
Then with one last hot kiss, she told me to behave myself, and I left.
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/mature/confessions-of-a-boytoy-part-7-teresa.aspx">Confessions of a BoyToy: Part 7, Teresa</a>