As I pulled into her drive, there she stood in the doorway, wearing only panties. Gypsy practically bounced out the door and jumped into my arms, wrapping her arms around my neck and her legs around my waist. We shared a deep hot kiss to celebrate our first day's success. Then we walked hand in hand back inside. She poured us a Tequila shooter as we settled in to talk about the appointments.
"Howdy," Gypsy started, "where have you been all my life? We made nearly a thousand dollars today! We could have been doing this for the last two or three of years if we had only known each other." She gave my crotch a playful squeeze and said, "I think you are a natural at this. You are a huge hit with my girlfriends so far."
I spent that night at Gypsys, and honestly, never slept better in my life. I awoke to Gypsy sucking my cock. What a way to start day two I thought.
"Hmmmm, I hope you don't mind. I'm just priming the pump." she giggled as she gave me a good squeeze and a long slow lick up my shaft.
"Go get ready for your day. You have three appointments. Your first appointment today is what we call a 'nooner' Howdy. Ms. Thompson is a very successful lady friend I have known for many years. Make damn sure she loves what you do for her. She is extremely powerful and can get us all the wealthy clients we could hope for Another thing Howdy, there is no way in hell you can be late. She runs a tight ship and as a favor to me, rearranged her schedule to squeeze you in at lunch time."
Looking my best for this appointment meant everything to Gypsy, so I wore a coat and tie. I took my Bimmer through the car wash and tipped the two bikini clad girls who detailed it 20 each. Remembering the encounter with Liz and Dee Dee made me want to test the waters with these two hotties.
Gypsy didn't have to drill into me the importance of being early. My parents had done a good job of that since I was young. Their words, "Fifteen minutes early is on time. On time is late!" echoed in my head. At least I remember something they taught me.
I pulled my freshly cleaned Bimmer in front of the office building downtown. The valet handed me a ticket and I walked through the large glass doors twenty minutes early. On time as usual I proudly boasted to myself. The receptionist greeted me as I approached her desk. Why was it I felt like every hot woman was flirting with me today? There was something about getting paid for sex that felt empowering, that made me walk just a bit faster. I exuded youthful confidence, and women are attracted to that.
"May I help you Sir?" the lovely young lady inquired with a million dollar smile.
"Yes, I'm here to see Ms. Thompson. I have a noon appointment with her." I said smiling at her, then glancing at her lips, then cleavage.
She blushed, "May I tell her who is here to see her Sir? I'm sure she won't be long if you would like to have a seat?"
As I waited, I walked over to a large wall that had the pictures of the officers and board of directors of the company. Stunned was an understatement when I realized that the Ms. Thompson I had an appointment with was in fact, the same Ms. Thompson that was a friend of my mothers.
"Oh fucking shit!" I said under my breath. "How the fucking hell am I going to get out of this?" I asked myself as the blood drained from my head and my cock simultaneously. My blood hastily retreated to parts unknown. "God, I'm feeling lightheaded! I think I'm going to throw up. So much for all this fucking self confidence." I mumbled.
"SIR! Hello! Ms. Thompson will see you now. I'm sorry to raise my voice at you Sir. I guess you didn't hear me calling you." She smiled as she stood and walked me towards a set of large paneled doors. Even in my panic, I couldn't ignore that this lovely lass had a very nice set of tits crowned with nice hard nipples that proudly begged to be noticed.
The door opened just as I reached for the ornate handle. There stood the ever radiant and beautiful Ms. Thompson. Ms. Thompson was a single woman of great elegance and social poise. She was a stunningly beautiful woman whose well tended to figure seemed better fitted on a much younger woman. Her solid silvery white hair had turned early in her life, and it quickly became her trademark. Along with her outward beauty, she had a very generous side and donated to every cause in town. After assuming control of the company her father had founded, she dedicated her life to shepparding it's growth. Her demanding lifestyle kept most suitors at arm's length.
She wore a beautifully tailored red business suit with a black lacy camosal that did a poor job covering her more than ample breasts. I wondered what the hell she would want with me I mused. Surely she was going to introduce me to a staff member, or someone I didn't know. No way this lady wants to hire me to fuck her. My mind raced through possible scenarios.
"Howdy!" she smiled broadly. "it is so good to see you again. It has been at least two years since I last saw you." She took both shoulders in her hands, feeling at my upper arms. "And look at you now...all tall, handsome and grown up." She leaned towards me and drew in a deep breath. "What a nice cologne you are wearing Howdy." Patting both shoulders, she winked, "Come in. Please come in."
Ms. Thompson turned to the receptionist and thanked her politely for helping me find my way.
"Veronica, please hold all my calls until 1 pm. This fine young man and I have some business to take care of." Her kind but firm look at the young lovely told her to get back to work.
"Yes Ma'am Ms. Thompson." she replied as she stole a glance at me before turning.
"Please come in Howdy and have a seat. May I get you something to drink? Soda? Tea? Mixed drink? she asked, closing the large door behind us.
"Oh no Ms. Thompson. I'm fine. Thank you. Very impressive office Ms. Thompson." I said as I looked around at the rare artwork and plush furnishings.
"Why, Thank you Howdy. But please, I want you to call me Melissa." she said as gave my tricept a feel.
Melissa gestured for me to take a seat and she sat on the edge of her chair facing me. Our knees were just a foot or two from touching.
"Howdy, I was a bit surprised to get the call from Gypsy yesterday. You know, she and I go back a long time. When she told me about her new business venture, and then told me she had a young partner named Howdy, I... " Melissa's eyes fell to the floor. "well, honestly Howdy, I couldn't believe my ears."
I sat petrified, glued to the chair as she spoke, swollowing down gulps of dry air. Was I in for a lecture on my apparent decaying morals and virtues from one of my mom's best friends? Had she already informed my parents as to my new calling and out of courtesy, was simply telling me about it first? There's nothing that can drain the blood out of a young man's dick faster, than thinking that his mom knows her son is getting paid to fuck women her own age. She would just die if she knew I was fucking any of her friends.
Melissa stared off some place behind me for a very long second before looking me squarely in the eyes. "Howdy, can you keep secrets? You know...Gypsy doesn't have a clue that we know each other. If you and I have any desire to conduct business together, this needs to remain our little secret." she said in a soft stern voice.
"What do you mean Ms. Thom... I mean Melissa? I'm trustworthy if that is what you are asking."
"Really Howdy? I'm glad to hear that, because confidentiality is what determines the depths of relationships." she said as her index finger rubbed at the corner of her lips.
Melissa leaned forward giving me a great view of the tops of her breasts, and then patted my knee. Then giving me a soul searching stare, her patting turned to a light carress, "I am glad we see eye to eye Howdy." she whispered before she sat back.
"You know Howdy, I'm so happy for Gypsy. I haven't heard her this excited about anything since her husband died two years ago."
She crossed her legs slowly, and put her finger to her lips, tracing them from corner to corner slowly. She sensuously pushed her skirt up and down her thigh. Acting as if she was inspecting the inside hem or something, she casually lifted and pulled the skirt to mid thigh, exposing the tops of her nylons and garter straps.
Catching me staring at her legs, she smiled, "You have no idea how happy I was to hear that you were her partner. I kind of lost track of you after you started college. For some strange reason Howdy, I always knew we would meet someday when you became a young man. Or at least I hoped we would."
"Howdy," she started as she leaned forward, playing with her nails, "you won't remember this, but one evening right after you graduated high school, I was visiting your mom and needed to visit the little girls room. I excused my self to go freshen up. As I walked down the long carpeted hallway, I noticed a sliver of light radiating from a door that wasn't completely shut. I knew your parents bedroom was on the opposite side of the house, so I gathered it must be your room. Checking behind me to make sure I wasn't being watched, I stole a glance inside."
Melissa figeted in her chair, licked to moisten her lips, and continued, "What I saw took my breath away. There you laid Howdy, legs open and facing the door. Your hand slowly pumped at your erect cock. The muscles in your powerful legs rippled as you responded to how good your hand felt. For a brief moment, I considered throwing caution to the wind and coming to help you."
Melissa's breathing was heavy and her nipples pushed hard against the soft fabric of her camasoul and light jacket. "Almost instantly, a rush of tingling heat surged between my legs. Howdy, I prayed my panties could contain the sudden wetness. Afraid to stay and watch for fear your mom would catch me, I tore myself away and found the restroom. I locked the door behind me and stared at the refleciton in the mirror. Melissa I shouted quietly at myself, you are twice his age and his mom is your friend."
"Yet the image of you stroking your large cock was permanently seared into my mind that evening. Out of desparation Howdy, I masturbated in your bathroom while dreaming of you fucking me. I dropped my pants to the floor and sat on your toilet with legs spread wide as my fingers pounded into me as I imagined you would. My lip was bruised from me biting it hard enough to keep me from crying out when I came. It took me several minutes for my juices to stop flowing I was so aroused. I haven't erased that memory to this very day."
Lacing her fingers together and holding them to her busom, Melissa smiled, "And now, here you are, sitting in front of me, about to give me the pounding I have dreamed about for over two years. I couldn't be happier."
Melissa stood and walked towards the doors. I watched her perfect runway stride as her round ass cheeks moved so sexily. She turned the lock, securing our privacy for the time being. Then as she walked back towards me, she pulled the clip from her hair, letting her silver white hair fall to her shoulders. She stood directly in front of me.
She turned her back to me and as she removed her jacket, she said, "Howdy, please be a darling and unzip my skirt."
My fingers felt clumsy as I first unbuttoned her skirt, then took hold of the pull. It slid down effortlessly. She stood there for a moment, then reached behind her, taking both of my hands and placing them on her hips, she reassured me it was ok.
Melissa placed her hands on mine as she leaned slightly forward and helped my hands slide her skirt over her shapely hips. She wore a black lace garter and panties, and had seamed thigh highs that ran down the back of her legs. Spreading her legs slightly, she took my hands and began rubbing her ass cheeks with mine. I got the hint.
As I caressed her strong legs through the nylons, her hips began to sway. I ran my fingers under the elastic bands of her legs, pushing her panties between her cheeks. Melissa moaned as I gave her panties a firm tug, rubbing them solidly across her clit. She pulled her black camasole over her shoulders and head, and tossed it on the arm of the chair. Then she widened her stance and bent over to rest her hands on the chair opposite me. Her thin waist and firm ass defied her age.
I ran my hands up the insides of her thighs as she pushed her ass towards me. Taking a few good feels at her warm wetness, I slipped my hands around her hips, taking charge of her. I pulled her ass into my face and she gasped at my boldness. My hands massaged at her hips, squeezing them roughly as I moved her lower body as I pleased. With my face buried between her cheeks, I ran my hands up her back and unlatched her bra. She shook her shoulders to make it fall to the chair.
Melissa moaned freely as my hands and fingers roamed her lower body, seeking out neglected curves and crevices. I slipped my hand between her legs, cupping her cunt and she let out a loud gasp.
"Oh my gawd Howdy. That's it. Yes, right there." she moaned as her body quivered.
Her hips began to move rythymically to my long hard strokes along her slit. Her panties were soaked and her juices coated my fingers and palm. I found her hard nub and rolled it in circles as gentle spasms caused her body to jerk.
"Pull my panties to the side and finger me hard Howdy. Make my pussy come alive."
I pushed between her shoulder blades, forcing her head down into the seat of the chair. She was there for my taking. Her silver white pubic hair was a stark contrast to her black lace. I pulled her panties to the side and stuck two fingers inside her drenched love tunnel. It must have been a long time since sweet Melissa had had a strange pair of fingers probing her pussy. She came right away.
I was surprised at how much muscle strength and control she had in her vagina. I'm not sure what I expected from a mature woman in her late 40s early 50s, but it contracted tightly around my fingers as they probed the depths of her walls.
"Faster Howdy. Make me cum again." she panted as she worked herself towards another orgasm. I pulled at her large rose petal lips as she began to tremble again. With my fingers open flat, I rubbed her clit and lips in rough quick circles. I buried my face in her hot cunt from behind and she let out a yelp. My long tongue fucked at her pussy like a small cock. She was surprised that I took the liberty to swat her ass hard and call her a naughty slut as I ate her out. She must have loved my boldness. Shortly after that, she reached behind her with both hands and spread her ass wide. I took turns licking at her sopping cunt and tightly puckered starfish until her strong grunts faded to long faint primal moans.
Melissa ran her hands through my hair as her body trembled. Faint moans and cries signaled small waves of pleasure still rolling through her body.
"Stand up and fuck me Howdy. I want to feel that cock that I have longed for pounding my pussy from behind."
I stood and was quickly out of my clothes. My throbbing cock hungered for her long neglected pussy. She reached between her outstretched legs and grabbed my cock, guiding it directly between her lips. She leaned back sharply, impaling herself on my throbbing cock. I was sure her loud gasp raised eyebrows outside her office. I reached under her and took both tits in my hands and squeezed them roughly as I started working my thick 8" of cock deeper inside her.
Melissa began bouncing hard up and down on me. Her hungry cunt had been deprived of a good fucking for far too long. My thrusts matched hers as she slammed herself over an over against me. Bracing herself on the arms of the chair, she pushed hard into me as she let out a sharp squeal and came hard on me. I grabbed both hips and pounded her hard and fast as I felt my orgasm building. Reaching under her, I pulled at her lips and cheeks, spreading them wide as I delivered the first load of hot jism deep in her. Her entire body tensed and shook as I felt her incredibly tight vaginal muscles grip my cock and she came again. The rush of my heavy load splashing inside her made her knees buckle.
We stood there motionless, my pulsing cock still buried inside her quivering pussy, dripping sperm in her. She slowly pulled herself off of me, our cum dripping from her love hole. Melissa pushed her hips back into me, feeling the length of my cum soaked cock slide along her thighs. Reaching between her legs to grab it, she milked the last drops of cum into her hand. Then she slurped every drop carefully into her mouth.
Melissa stood upright and turned to face me. "Howdy, I would love to kiss you like I meant it, but I neglected to bring my lipstick with me this morning. Will you give me a raincheck on the kisses?" batting her long lashes.
I stood there in amazement that I had just fucked one of my mom's best friends, and had completely enjoyed the hell out of it. My semi erect cock brushed against her and she took hold of it, stroking it slowly, rubbing it across her tummy as she peered into my eyes.
"Next time we meet my dear Howdy, I will replace the hot sticky cum on your cock with bright red lipstick. Deal?"
Melissa pressed her beautiful semi naked mature body into mine as she looked up and blew me a kiss. "So Howdy, will I see you again on business? Or will it just be when I visit your mom?"
She glanced towards the antique grandfather clock as it chimed 12:45. "UH-OH, time really does fly when you are having fun Howdy." She said with a pat to my ass. "Next week. Same time?"
"Oh course Melissa. I loved every second of this!" I said as my cock throbbed in her hand.
"Please tell Veronica to put you on the schedule for the same time every week." Melissa said before she closed the door into her private bathroom.
I hurriedly dressed and on the way out, asked the lovely Veronica to handle the scheduling for us. Veronica looked at me with a suspicious smile. "Your tie is crooked mister." she said with a wink. "Let me give you a hand with that."
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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-4-sweet.aspx">Confessions of a BoyToy: Part 4, Sweet Melissa</a>