"What do you mean?" I asked Charlie's friend in disbelief. "Are you saying you will pay me to have sex with some of your lady friends? Uhhh , are you serious?"
It seemed like I was entering someone else's fantasy. This would certainly beat the hell out a real 9 to 5 job at the hardware store, or mowing yards all summer I thought.
I was nearly twenty-one, was going to college and living the good life. It wasn't like I was starved for affection, but I admit to wandering in and out of short term relationships like they were stores at the mall. The girls I dated weren't boring by any means, it's just that I was so easily distracted by anything beautiful in a skirt. All of this peace, love and 'free sex' stuff was my motto up until I met Gypsy, a good friend of my friend Charlie.
Charlie was a bass guitarist at a popular Houston night club and ran around with a gorgeous hot blond named Jan. In their prime, his band was a very good band and they opened for some of the biggest headliners of the 60s and 70s. Charlie was about 10 years older than me and took care of me like he would a younger brother.
If Charlie hadn't been such a nice guy, I swear, I would have banged Jan for sure. Jan and I often sat together and drank while we listened to Charlie's band. Most of the time during sets, we hit the dance floor together. Charlie didn't mind Jan and me dancing because he knew I could, and would take care of Jan if need be. Jan, on the other hand, took great delight getting me rock hard on the dance floor just to leave me stranded.
One night after several in our group closed down the club, Charlie and Jan asked me if I wanted to meet one of their friends. Charlie told me she went by the name Gypsy Savage and was in her mid forties. I've always preferred women a few years older than me, but this was a bit beyond my age preference, but a friend of Charlies is a friend of mine, so I agreed. So we piled in my BMW and headed to Gypsy's house a few miles away.
"Gypsy is a free spirit my friend." Charlie blurted. "But don't let that fool you. She is a brilliant business woman who just happens to be very hot. Take care of her and I promise you Howdy, she will take very good care of you." he added with a broad grin.
We pulled into Gypsy's long driveway about 3 am. According to Charlie, Gypsy's husband died from injuries suffered in a horrible accident a couple of years earlier, and she had recently been awarded a massive insurance settlement. So Gypsy now had the luxury to pursue whatever pleased her.
As Led Zeppelin's Stairway to Heaven
blared away inside, the distinctive aroma of a highly popular medicinal herb drifted from the back door into the four car port-e-cache. Gypsy stood swaying in the doorway and was wearing nothing but a floor length semi-shear nightgown and a big smile. The warm glow of interior lighting behind her silhouetted her shapely figure. Gypsy may have been in her mid 40s, but she was beautiful and still had the body of a much younger woman. She was just over five foot tall, big brown eyes, long curly brown hair, and had a smoking hot body.
After making a hasty introduction, it didn't take Charlie and Jan long to excuse themselves to the back bedroom, leaving me to the lustful care of Gypsy. She offered me a puff off of herhand rolled fattybut I declined, so she poured us both a shot of Tequila. After three shooters, she was out of her gown and rubbing her luscious body all over me as we kissed.
A few short minutes later, she had my pants around my ankles and she sucking at my throbbing cock. Gypsy sucked at my cock until I delivered a hot stream of cum into her open mouth. Then she pushed me backwards onto the couch in the living room and straddled me. She rubbed her small firm tits back and forth in my face as I took turns sucking each hard nipple. Gypsy was so wet she slid her tight little pussy all the way down on my throbbing cock with one hard push. She was in such a mellow state that we fucked for over an hour before she came in a very vocal, body shaking orgasm that soaked me and the couch. I couldn't believe what a tight pussy this forty something year old woman had. I don't know what I was expecting, but it wasn't this. We collapsed onto the couch laying side by side facing each other.
"Howdy" Gypsy started, followed by a deep drag on her hand rolled smoke, then a long pause. She studied my face as she held her breath. Then as she exhaled slowly, she whispered , "Have you ever thought about renting that nice big cock of yours to women like me? You know, slightly older women whose hubby isdead or dead in the bed. You know what I mean man, the kind who care more about making money than making love to their woman?"
The haze in the room made it easy to laugh at such a thought. "What do you mean Gypsy? You're kidding me right?"
Gypsy smiled and squinted at me through glassy eyes. Then with a deep soulful giggle, she patted my face and said. "I'm as serious as a satisfied high- dee -ho can be. I'll be your business manager and handle all the appointments for you. All you have to do is show up on time at whatever address I give you, and then do whatever that lady wants you to do for her. Are you game Honey?"
Gypsy continued as she slowly exhaled another smokey giggle. "I'm serious Howdy. You will get all the pussy and ass you will ever want. And you and I will make a small fortune. Of course, you will be expected to fuck yourpartner on a regular basis."
"Do I get paid overtime for fucking my partner?" I laughed.
I marveled at the notion that a beautiful woman would actually pay for a guy to fuck her, but there was no reluctance in my desire to plant my cock in as many of those horny old hot pussies as I could. So, just like that, we were in business.
"Okay Gypsy. Let's do this. We have nothing to lose, right?" I extended my hand to consummate the agreement, but she insisted that if we were going to shake anything, it would be her ass on my cock.
We fell asleep at some point during the wee hours of the morning and slept until after noon. The smell of breakfast and coffee permeated the room and I was starving.
"Get up partner." Gypsy said, you have work to do, giving me a pat on my naked butt.
Gypsy had on a pair of very short cutoffs that only covered the top two thirds of her tanned ass cheeks and a shear tank top that left nothing to the imagination.
"Grab a quick shower partner while I finish making you breakfast. You're going to need your strength today."
Over breakfast, Gypsy shared her plan of our partnership with Charlie. Charlie and Jan thought the notion of a woman actually paying me, their friend Howdy, for cock was hysterical and busted out laughing. It sounded funny to me too and I joined the laughter.
Gypsy looked Charlie square in the eyes with a poker faced stare and asked, "Charlie, has Howdy ever had his big fat cock in YOUR pussy? It's money in the bank baby, and we are gonna cash in."
Then her expression turned towards Jan and echoed the same question of her. Jan giggled a big smile, shrugged her shoulders and said, "No, not yet."
I was happy at the thought of getting paid to do what I would have gladly done for free. They could laugh all they wanted as far as I was concerned. All my buddies had to beg their girlfriends for any sexual favors and then worry about their girlfriends daddies finding out. And here I was about to get paid for those same services.
As we sat having breakfast, Gypsy's home phone rang. "Hello Barb." she said cheerfully to one of her girlfriends. "Thanks for calling me back. Do you remember a conversation you, the girls and I had a few weeks ago? You know, THAT conversation? Well, I have just the right person to fill that order for you. Uh, no Barb, he doesn't work pro bono ! But I promise, you will love his nice thick hard ' bono ' though, Just don't expect it to be free. Barb honey, it doesn't matter how attractive you are dear, he is working his way through college and you are going to help him out. Agreed? I'm giving him your address and you make sure to give this nice young man a crisp new Benjamin or two when he's through. Muahs ...Love you."
Gypsy hung up the phone and smirked a 'I told you so' towards Charlie and Jan. Then she turned to me with a huge smile, "Okay partner, we're officially in business. Here is Barb's address. Be there at 3 this afternoon. She is a wild one, so don't let her intimidate you Hun . Call me from her house after you are done and have showered. I will have you another client for early evening, say, 6 ish. After you are through with your late afternoon call,meet meback here."
I remember being unsure of the whole notion of becoming a male hooker. I had always been the one on the prowl, the aggressor by nature. I enjoyed the hunt and the capture for sure. Now, I was having the tables turned on me. But hey, getting pussy is getting pussy. Now, this woman I met less than 24 hours ago, was farming me out for stud services to her friends. Oh well, the money sounded too damn good to refuse, and now, there was no way to gracefully bow out.
Even though I had a relatively nice car, it was totally out classed in Barb's neighborhood. She lived in a gated community long before gated neighborhoods were fashionable. The guard at the front gate looked at me with a suspicious eye as I asked for directions.
"Are you one of Barb's son's friends?" he asked as he raised one eyebrow.
"Honestly sir, I don't know if Barb even has a son. I'm here to see her about some personal business Sir." I answered in a wavering voice.
"Good answer kid," he said drumming his fingers on the side of his holster. "Barb doesn't have any sons. In fact, she doesn't have any kids period." he added. Then he took a step back from my car, and lightening up a bit, he offered directions as the massive front gate rolled to the side.
Every lawn in the neighborhood was manicured to perfection. This place was like nothing I had ever seen. Each mansion sat on a few landscaped acres and was uniquely spectacular. It seemed like every mansion had a gang of workers in the yard doing something. I pulled my little Bravarian red rocket up in front of the most beautiful mansion I had ever seen. In the long sweeping circular drive out front was a new black Silver Cloud and a red Ferrari.
"Whatever it is her husband does, I wanna do it too." I mumbled to myself.
I felt a bit awkward and out of place, but I had a job to do, and I was going to make it happen. My mind was made up and I was determined to make this Barb woman the happiest woman on her street. I can do this I said to myself, attempting to bolster my confidence as I walked towards the large front door.
The door bell rang like church bells echoing through empty cobble stoned streets. Without being too obvious, I peered through the eight foot tall leaded glass doors into the large entry . I could see all the way through the house, and past enormous plate glass windows into the pool area in the back yard. As I reached for the bell again, an older man in a black suit and tie opened the door.
"May I help you young man?" the finely tailored gentleman asked in his best stuffy voice.
"I'm here to see Barb." I said, extending my hand to shake his.
Without flinching, he glanced downward at my extended hand and rolled his eyes. "Follow me Sir. What is your name so I can properly introduce you to the Lady of the house?"
"Howdy." I replied.
He stopped and briefly, looking over his half turned shoulder at me in disbelief, "Howdy is a crude form of salutation Sir, not a name."
"Howdy!" I heard a chirpy youthful voice call as my name echoed off the rich cherry wood paneled walls. "Is that you?"
Barb came walking briskly around the corner. "Howdy, it is so good to meet you. I have heard glowing reviews about your work. I can't wait to find out for myself." she said as her eyes gave me a quick me up and down several times.
In classic form, Barb took both my hands in hers, lifted one foot to knee level behind her as she leaned into me and pecked a kiss to each of my cheeks. Barb was a stunning woman in her late 40s or early 50s. She had piercing green eyes, coal black hair, beautiful thin lips and long shapely legs that were accentuated by the 4 inch heels she wore. In contrast to Gypsy's dark tan, Barb had almost no tan whatsoever. Like Gypsy though, she had a beautiful shape for a mature woman. Her very presence exuded refinement and confidence, plus she wore an intoxicating perfume that I couldn't get enough of.
Her lustful hungry smile turned professional in the blink of an eye as she turned and politely excused the elderly gentleman who had answered the door.
She slipped her hand between my chest and upper arm, and squeezed my bicep as she invited me into the great room. "Howdy, I am so happy you had time to see me with such short notice. May I pour you a drink? You are old enough to drink, right Howdy?" Barb teased with a smile. "I wouldn't want to contribute to the delinquency of a minor you know." She said giving me a playful wink.
"I'll have whatever you are having Barb." I answered returning the smile. "And for the record Barb, I AM old enough to drink. You don't mind me calling you Barb do you?"
"Not at all. Here in a little bit, I hope you find some nice new naughty names to call me Howdy." she said with a deep heavy sigh as her eyes undressed me.
Barb fixed us each a drink and motioned for me to sit in a plush chair opposite hers. Her short designer skirt slid more than half way up her thighs as she sat down. As she sat provocatively posed with knees slightly parted, I think she was asking herself how long she thought it would take before I peeked between her long slender legs. For the most part, she sat relatively still, only shifting her legs slightly from side to side as we chatted. But each time she moved side to side, her skirt served up more smooth creamy flesh to tempt me. She kept her gaze fixed on my eyes as she began to slowly turn up the seduction meter. Barb's soft spokenness was both soothing and alluring.
We made small talk as we both grew more aroused by the suggestive nature of our conversation. Her large hard nipples poked proudly at the green silk blouse that matched her eyes. Barb was becoming a bit more restless as she adjusted her sitting position several times. She cooed as much as she talked. Her breathing was becoming labored and her hands constantly brushed at her thighs or nervously played with the diamond necklace that caressed her cleavage.
Two can play this game I said to myself as I casually moved my hand to my thigh, just inches from my crotch. I widened my legs to make sure she noticed the effect her erotic behavior was having on me. My fingertips slowly rubbed my erection through my pants, signaling to her that I was paying attention to her every seductive move. Barb licked her lips before giving her bottom lip a gentle bite.
I raised my drink to offer her a toast. "To you Barb, my new friend."
She leaned forward to tap her glass with mine. The tops of her large tits pushed at the top button of her blouse, popping it open. Our eyes were already fucking each other. We were just waiting for our bodies to officially surrender.
Barb slumped back into her chair and took a couple of very slow deep breaths. With her eyes glued to mine, she took a long sensuous sip from her drink. Then holding the glass to her lips, she extended her tongue slightly and ran the tip back and forth across the crystal rim. Her seduction was fully underway. Her posture was now anything but lady like. Her skirt had ridden up so high, I could see the darkness of her pubic hair through the fine lace. She reached into her drink and pulled out a single ice cube.
"It's getting hot in here. Don't you agree?" Barb purred as she ran the cube across the tops of her breasts.
The heat of her skin melted the cube quickly and small trickles of cold water disappeared between her breasts. She held the cube over each nipple until drops had soaked through her blouse and bra. Then Barb leaned forward and offered me what was left of the cube. She rubbed the ice cube across my lips.
"Suck on this." Barb whispered as she slipped the remains of the cube between my lips. "Maybe it will cool you off too." she said as her hand fell to my knee before she leaned back again and kicked off her heels.
Without breaking eye contact, Barb set her drink on the marble topped table by her chair. She laced her fingers together in her lap as a feeble gesture to hide her growing passion. With eyes glued to mine, she lightly ran her fingertips across the tops of her breasts. Her left leg swayed slightly from side to side giving me a better view of her wet crotch.
As her nails seductively traced the upper curves of her breasts, her other hand slipped between her thighs. She rested her fingers at panties edge as if seeing what my response would be. Matching her move, I gave my fully engorged cock a few tugs through my pants as if brandishing my manhood in response. Barb leaned her head back against the plush chair and her eyelids fluttered as her fingers pushedthe wet lace firmly between her lips. Then her thighs squeezed her hand tightly as she shuttered for a moment. She moaned a faint gasp before she bit at her lower lip in an attempt to suppress her mounting excitement.
Finally, out of desperation I guess, she cleared her throat and tried to gather herself.Barb suddenly sat upright, silently facing me for a long moment, then changing the subject, invited me to join her for a tour of the house. As she leaned forward and reached for the arms of her chair, her knees widened, giving me a great view of her soaked lacy white panties. She stared at me as I stared at the thin veil of lacy protection that shielded her womanhood from my starving eyes. As if on queue, we both licked our lips and our eyes locked again on each others. We stood up, just a couple of feet from each other, eyes begging the other to make the first move. Barb's eyes widened as she looked down at the large bulge in my pants.
"Oh my gawwwd Howdy. Is that for me?" she asked in mocked surprise as a hot breath pushed the words through her pursed lips.
Barb half way closed her eyes as she reached for my forearm to steady herself. Her touch sent a bolt of energy coursing through my body. I know she felt it too. It seemed like an eternity since her body had felt this alive. Every cell in her body cried out to be caressed, to be appreciated, and to once again, be set ablaze with passion. She looked at me and said the full tour would have to wait. She was only going to show me one more room today, her bedroom.
Barb led me into a bedroom the size of most people's home. It was full of every amenity and fine furnishing money could buy. With her fingers entwined in mine, she lead me to her large circular bed. Then for the first time, we shared a long heart pounding kiss. Barb's lips were like velvet. Her tongue darted in and out of my mouth as her hands fumbled to unbutton my shirt. Barb kissed me as if making up for lost time. Her hands groped at every muscle in my chest and arms as she explored my body. Her kisses were hot and choppy as she worked frantically to unsnap and unzip my pants.
Finally, she had tried hard enough and pushed me onto my back. Grabbing my pants by the waistband with both hands, she yanked my pants, boxers and shoes off in one swift move. I laid there naked, legs wide as her eyes feasted on my thick long cock. She fell to her knees between my legs and pushed at my knees to force them wider. Then she began to kiss and nibble at one thigh then the other. My cock was throbbing as she finally reached for it with both hands. Barb firmly held my cock in place as she sucked my balls into her mouth, licking them. She gripped my shaft forcefully as she stroked it several times before releasing it completely. Barb kept her eyes fixed on my cock as it stood pulsing proudly, awaiting her next move.
Then she began slowly licking my shaft up and down as she played with my balls. She slurped at my large bulbous cock head before engulfing me totally between her incredibly soft lips. Through cock muffled moans, Barb begged for me to cum in her mouth as she began pumping my cock vigorously. I held her head I place as I rammed my love muscle down her cock hungry throat. After several deep throat thrusts, she pulled my cock from her mouth, and artfully flicked her tongue around the head as precum began to dribble out. She moaned even louder knowing I was going to fill her first demand.
Barb and I both felt my orgasm stir from deep in my balls and her voice became more excited and higher pitched. "Fuck my mouth you naughty little boy. Cum in my mouth! Cum in mommy's mouth!" she groaned between deep sucks. Her saliva lubricated my cock as she worked to make me cum.
She felt my sperm surge through my cock and she cried out loud as I shot a large stream of cum across her open lips. My load was large and thick. It splattered her face and splashed onto her tits. She engorged herself on my cock, licking and sucking my cum feverishly .
"Oh my gawwwwd . Fuck me. I want you to FUCK MOMMY NOW!" she demanded.
I pulled Barb onto the bed with a handful of her thick black hair. As she sat straddling me, and before I could reach to unbutton her blouse, she yanked at the front of her blouse, sending buttons flying. She pulled her blouse off and forced her bra above her tits.
"Suck my nipples young man. Make mommy happy." Barb moaned as she fed a large nipple into my mouth. "Oh gawwd Howdy, that feels soooo good. Bite them and squeeze them hard! Make mommy cum for her little boy."
Barb squeezed at her own tits as I pushed her skirt over her gyrating hips. Then pulling her panties to the side, I rubbed the head of my cock back and forth in her wet cunt. She was nearing an orgasm herself and didn't need much more stimulus in order to completely let go. I rubbed her swollen clit with the head of my cock as she ground herself on me. Then Barb arched her back and her entire body tensed up tightly. She let out a deep moan and came hard on me.
I laid underneath her, feeling her body tremble as waves of orgasms shook her body. Then I slapped her ass cheek and thrust my cock deep inside her in one hard swift motion. She cried out as I stretched her neglected cunt wide. Her nails dug into my chest as she felt my cock throbbing deep inside her walls. Then leaning back to allow deeper penetration, she began to rock on me. She worked her pelvis in slow circles that grew wider and harder as she became comfortable with my size ramming inside her. Her grinding and rocking became violent bouncing as she released years of her stored up passion on my manhood.
"I'm going to cum baby." Barb moaned as tears began to stream down her face. "You're gonna make mommy cum baby. She groaned loudly as she bucked wildly on me. "Cum with me. Make this cunt yours little boy. FUCK MOMMY HARD!" as her hips plunged her hot cunt harder onto my cock.
Barb's body went completely out of control and she thrashed about on me. She came several times, sending streams of her hot juices all over me. Her pussy gripped at me like that of an 18 year old virgin. She finally collapsed on top of me again, smothering me in kisses. I ran my hands all over her body, touching her in the most caring and sensuous way. We kissed passionately for several minutes before she lifted herself off of my cock.
"Howdy," Barb started with a quivering meek voice, "would you like to see me again? Like, maybe every week? Or even twice a week? she softly asked as her eyes begged for consent.
I brushed the hair from her face and told her I would love to see her as often as she wanted.
"Really?" she asked, almost surprised at my answer.
Barb leaned up on one elbow, her beautiful tits pressed to my side, and kissed me again. "Good! That makes me happy. And trust me, you will like me even more when I'm really happy."
I returned a long wet kiss. Then Barb told me Gypsy wanted me back by 5pm and I was going to need to grab a quick shower and leave. Barb and I shared a nice hot shower together, then dried and dressed.
Giving my butt cheek a squeeze and a hard swat, she added, "I would love to walk you to your car and fuck you in front of the house. But somehow, I don't think the neighbors would approve. B-U-U-T-T... My husband's brother lives across the street you know. The boys own an oil company and spend most of the time overseas."
Barb thought for a moment, "Come to think about it Howdy, I do believemy sister in lawhas some special chores you could help her with. I should probably warn you about her, but some things are best discovered on their own." she said giggling. "Howdy, you do accept referrals don't you?"
Barb's smile beamed even greater as she walked me to the front door. She discretely handed me an envelope and said she would be speaking to Gypsy about getting on a regular schedule. Without looking at the contents, I thanked her warmly, folded the envelope and slipped it in my shirt pocket.
"Barb, I can't wait to see you again. Let's do something really wild next time!" I whispered.
There was no place for a hot kiss goodbye. Mister stuffy shirt met us at the front door to insure myprompt exit. "Have a nice day, H o w d y." he mutteredmockingly as he closed the door behind me.
I waited until I was out of the neighborhood to open the envelope. Inside were five crisp 100 dollar bills. I can get used to this in a hurry I thought as I stuffed them in my shirt pocket.
A few minutes later, my cell phone went off. It was Gypsy. "Well well Howdy. Barb'ssister in law just called to arrange a time for you stop by. Write down this address for your 6 pm appointment this evening, and call me when you are on your way back."
I had no idea how my 6pm appointment could ever top Barb, but I intended to find out.
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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-1-in-the.aspx">Confessions of a BoyToy: Part 1, In The Beginning</a>