"Just another beautiful day in paradise baby." Gypsy said happily, squeezing my hand.
"You just wait Gypsy. It's only gonna get better!" I replied with a wink.
It was the perfect morning to drop the top on her El Dorado and cruise the roads around the lake. We headed to our favorite breakfast spot that over looked Clear Lake. It was a hideaway mostly frequented by astronauts, locals and hungry fishermen. As we strolled out the pier to the barge now turned restaurant , seagulls circled overhead, occasionally dive bombing, begging us for freebies. The morning breeze was crisp and held it's grip on the night's chill longer than usual. That was one of the bennies of living on the upper Gulf coast, moderate temps year round.
Gypsy and I had been partners in this little venture for nearly eight months now. It boggled my mind to know that we had made over 175,000, eight inches at a time! Gypsy knew I wanted to get back to Texas A&M, and that the number of days left in our venture were dwindling.
It's a funny thing about people who develop a deep unselfish love for each other, they are always looking for ways to show their love and affection in new and exciting ways. They can never seem to be able to out give each other.
Neither of us had a clue before that morning, that the other had planned a surprise.
Like every time before, we sat in Peg's section in our usual corner booth that overlooked the marina and the Kemah drawbridge beyond. Gypsy had a mischievous playful side and delighted herself in giving me a hard on at the most inopportune time. She usually threw caution to the wind and was willing to do things in public most people would not approve of. But, like or not, that was Gypsy.
Peg had seen us coming and hurried to have our coffee waiting for us on the table as we sat down. Peg was a charming lady with a quick wit. Time had been tough on her though. Homemade tattoos along her arms and legs hinted to time spent behind bars. A noticeable limp and badly stained teeth never stopped her from sharing her heart felt smiles or her unsolicited pearls of wisdom. She was just a hard working gal who wanted to make a better life for her kids than the life she inherited. But she never played the woe-is-me card. She just worked a bit harder, smiled a bit bigger.
I felt Gypsy's barefoot start it's ascent up my leg. I gave her the 'really' look and she giggled. Peg was standing right next to us just yapping away, oblivious to the events taking place under her nose. I pinched Gypsy's little toe and she gave out a little yelp and made a funny face at me. Peg stopped only briefly before continuing her verbal diarrhea. I'm sure we weren't the only ones who had had a little fun in the booth. If Peg ever figured out what was happening under the table, she never let on.
Gypsy could make me hard with a single stare or gesture or touch. As her foot rubbed up and down my cock, I looked her in the eye, "You, young lady are in deep deep trouble when we get home."
Gypsy didn't say a word. Her look spoke for her. She had that just-dare-me-to-slip-under-this-table-and-suck-your-eyeballs-out-through-your cock look. I knew not to tempt her. This place might show up on our growing list of eateries we have been invited to not return to.
Before our food arrived, Gypsy and I acted like junior high kids with their first crush. We both had something important to say and our nerves kept us acting silly instead. Finally, after a lull in the excitement, we both blurted out each others names as we reached across the table for the other's hands. We laughed at our timing.
After being together almost constantly for eight months, we found ourselves finishing each other's sentences and reading each other's minds. Gypsy had invited me to move in with her after just one month of working together. She didn't have to ask me twice. To say we had become highly compatible was an understatement.
"Howdy," Gypsy said tearing up as our conversation turned more serious, "I know you want to go back and finish your degree. And I am behind you 110%. So," she hesitated, looking out the plate glass window as if what she wanted to say was written on a passing boat.
Gypsy had a hard time saying anything emotional or tender without tearing up. That was just one more enduring quality I found irresistible about her. Our fingers played with each others as she choked back tears, trying to get her words out.
"Howdy, you have made my life fun again. After my husband died, I didn't know if I wanted to go on living to be honest. But somehow, day after agonizing day, I managed to keep going. Alcohol and weed kept me numb long enough for me to figure out that I did want to live. Then Charlie and Jan brought you to me like a new puppy, how was I going to refuse a gift like that? And look what has become of it."
"Gypsy," I butted in, "A&M is just a couple of hours from here. I will be home on weekends. We will still be together and we can even keep a few appointments if you want. You mean the world to me Gypsy! We will still be partners and lovers, if you want us be that is."
Peg inadvertently interrupted us with the cheerful announcement that breakfast was now served.
Gypsy unrolled her silverware and dabbed her napkin in the corner of each eye, blotting her tears.
"Gypsy, I have a little surprise for you later today when I get through with my appointment. So be ready when I get home."
"No way Howdy?" Gypsy said, a fresh smile filling her face. "And just what kind of surprise might that be young man?" she asked in her prissy bossy voice.
"Something very special for the most special lady in the world! You know I can't spoil your surprise now don't you?"
As our breakfast grew cold, Gypsy beamed. "Well Howdy, I have something to give you too. I want you to have it now, so you can use it for school or for whatever else you see fit."
Gypsy, glanced around the room, making sure we weren't being watched. Then she stuck her hand in her shoulder bag and pulled out the fattest legal sized envelope I had ever seen. She placed it on the table and slid it towards me with a big happy smile. On the front was a smiley face, a big 'X' and 'O', and six words, For Howdy, I Love You, Gypsy. My mouth fell open when she said that she had been saving her half of our earnings to give me for a special day. Today she had determined, was that day.
"Gypsy! I can't take that!" I said, shaking my head 'no', pushing the unopened envelope back towards her. "You are my partner. That is your half of the earnings. Without you, I would have mowed yards all summer and made, maybe a grand. Thanks to you, I'm pretty damn well off for a twenty one year old guy. In fact Gypsy, my half alone more than doubled what both my parents made for the whole year. All of my success is because of you Gypsy!"
"Howdy," Gypsy started, as her voice faltered slightly, quivering as she tightened her grip on my hands, "you have been very respectful of the life I lived prior to our meeting. I have often thought to myself, that if you ever asked, I would tell you anything you wanted to know. But, to your credit I suppose, you never brought it up."
"My husband was a very successful business man Howdy. When most people were making 20-25 thousand a year, he was making over three million a year. For the seven years prior to his death, he made over 25 million dollars. On top of that, he had just sold his interest in three different companies the month before his tragic death. That money comes in every month like clockwork. Howdy, that amount alone is mid six figures a month."
Gypsy sat there glassy eyed, in deep thought before finishing, "It was almost like he knew something was going to happen to him and he didn't want me to have to deal with the messy details. In short, even without the large insurance policies, even without the large wrongful death settlement Attorney Jamail won for me, Howdy, someone who loved me dearly made sure I was set for life."
Gypsy's focus seemed to drift off as she spoke. Understandably, she rambled as she talked fondly of him. She carried on as if their life together was now a distant memory, when in fact, it had been just two short years since he had died.
"Howdy, your birthday party was a big damn deal to me. Not just in the fact that I wanted to do something very special for you, but I wanted to do something that no other young man your age would have. The day of your party was in fact, the bitter sweet anniversary of my husband's death."
Gypsy's eyes dropped, "Selfishly, I wanted to, I disparately needed to, replace the memories of that day with something happy. The scabs that covered my pain needed to be ripped away so I could start to heal. I wanted the pain to be replaced with happiness and pleasure for someone I was growing to love. The party turned out even better than I planned."
"Howdy, when you made such passionate love to me in front of all the girls, that for me it was a message to all of them, that no matter how hard, no matter how good, no matter how long or many times they fucked you or sucked your gorgeous cock, I was the only one that you really made love too. The way you made me feel in front of them restored my heart. I started feeling like a whole woman again."
"Howdy, throughout that weekend, every single one of them called me to tell me that was the most beautiful thing they had ever seen. The way you loved me endeared you to them in a special way. How do I ever repay you for that? Howdy, that is why I can confidently send you into the cougar's den time after time. I don't need to be jealous when you make love to me like that."
"There's so much more Howdy." she said, her voice trailing off. "Stop me if you have already heard too much.
I sat there stunned, statuesque, unable to speak or comprehend all that my ears had heard. It was also the first time the 'L' word had been used to describe how either of us felt towards the other. In eight short months, Gypsy had managed to turn my life completely up side down. I had no idea that I had had such an impact on hers.
"Gypsy, I don't know what to say." I said as my eyes began to water too.
"Start with, Thank you Gypsy!" Then take me home after breakfast and fuck me like I'm your new bitch.
We both laughed. "I can sure as hell do that Gypsy. But, I would have fucked you like that for free baby."
We finished our breakfast and Peg brought our bill. I looked at Gypsy as I pulled money out of my wallet to pay. Gypsy gave me an approving wink and I opened the envelope. I pulled out a stack of hundred dollar bills that wore a band around them that said 2,000.00. Then I handed her the stack and a twenty and told her that should just about cover it.
"Keep the change Peg. Thank you for always taking such good care of us!"
Peg stood there speechless as we left. By the time we walked out the front door and passed by the large windows where we had sat, Peg was whoopin' and a hollerin'. Gypsy and I couldn't have been happier.
I took Gypsy home and fulfilled her request. We fucked like teenagers on prom night, completely losing track of anything other than how much we loved pleasing each other.
"Howdy," Gypsy said as we laid in bed, "as you requested, I only set up one appointment for you today. It's with Margot, the real estate broker. She said for you to meet her at her house around noonish. She is having a girlfriend or two over for drinks and wants you to be her cabana boy. It's just two grand, can you handle three women for two hours for that paltry pay?" she said with a giggle as she waved my cock in circles.
Gypsy didn't let go of my cock until she had climbed on top of me. Then she leaned down on me and we kissed the most intense kisses I had ever tasted. My cock was more than hard and wanting her all over again. As I nudged my tip into her wet cunt, she pulled away and insisted I get ready for my appointment.
"Tonight Howdy, after you give me my present, we will pick up where we left off." she said, pinching my cheek.
Margot was like all the other women Gypsy and Melissa knew; rich, powerful, oversexed and under serviced. I found a note taped to Margot's front door, telling me to come on in, they were in the back. Her home looked like pages from magazines.
Before I announced my arrival, I stood at the plate glass window for a couple of minutes, admiring the three naked beauty queens as they playfully nudged and touched each other. My cock twitched several times, readying itself for the call of duty. I studied the magnificent mature bodies of each of them, noting beautiful unique features. Margot had a neatly trimmed landing strip a few shades darker than her sandy blond hair. Her large tits sported large brown nipples half an inch long or longer. The other two women looked to be maybe 12-15 years younger than Margot and equally delicious. Even though I had not met them yet, I was eager to see their version of a three on one fast break.
I rapped on the back door and opened it to a chorus of hellos. They looked like they had started the party without me. The smell of hot wet pussy made my nostrils flare. Margot made a slathering introduction of me to her girlfriends, Heather and Jacki. The bulge in my shorts was evident, and well received as all three quickly concurred that I was overdressed for the occasion. Eager to comply to my customers wishes, I slipped off my shorts and t-shirt.
The appointment with Margot went as expected, me serving Margot and her two girlfriends drinks while I wore my just my speedo, sunglasses and flip flops. It didn't take more than a half hour or so before Margot suggested that it just wasn't right for me to see them naked and that I should return the favor. Not one to argue with a client, off came the speedo. As my speedo slipped past the end of my semi-erect cock, it made a bounce upward, much to their delight.
Of course the obligatory application of sun tan lotion soon followed. I joined them on this huge contraption Margot had had especially made. It was a king sized bed with weatherproof mattress and pillows that hung suspended from a massive frame that allowed it to swing freely back and forth in any direction, or in circles, or all the above. It was positioned about one third way over the pool so that if one wanted, they could merely roll off the bed into the pool.
I sat between Margot and Heather, with legs open, facing Margot as I did my best to rub lotion on both of them at the same time. My erect cock pointed right at her hungry lips, maybe two feet away. Margot considered that her invitation and slid her hand up my thigh, taking hold of my erection.
"Look what I found girls." Margot waved my growing erection as if it was a carnival prize.
This was the third time for me to fuck Margot. She was a cum spitting, fuck machine with a huge sexual appetite. She had a tendency to get nasty pretty fast the first two times we were together. I knew I was going to have my limits tested for sure. After giving my cock a few good pulls, Margot scooted towards me until she could get her mouth over my head. She coated the head with her saliva as it trickled down my shaft. Her petite mouth stretched wide as she slid me down her throat. Her tongue caressed my shaft as she glided up and down on me.
I leaned back next to Heather as she ran her hand across my chest and then down my stomach. Heather played with my balls and whatever cock that wasn't in Margot's mouth. Then she took my cock in hand and pulled it from her mouth. Then she slapped Margot's face with the head several times, calling her a selfish nasty cunt. Droplets of Margot's own saliva splattered off my cock onto her face. Margot responded with a few compliments of her own directed towards Heather.
Jacki, the third woman, positioned herself on all fours, watching Heather feed my cock to Margot. I ran my hand over Jacki's smooth flesh and introduced her body to my gropes and squeezes as her ass wiggled to my rough probes. She squirmed and gasped as my fingers filled her tight cunt, but kept her focus on Heather's pumping action. Margot slurped at my cock like it was her first taste.
Margot had one hand under Jacki, rubbing her clit as her other hand rubbed her own. I slipped my hand behind Heather's thigh, squeezing it roughly as my fingers made landfall between her drenched lips. Heather leaned up to give my probes more access. Soon, Heather had swung her leg across my face and was grinding her sweet tasting pussy in my face as she continued feeding cock to Margot.
Jacki was the first to come. She let out a beautiful moan as she bathed our fingers in her orgasm. With my face buried in Heather's sopping pussy, I barely heard the three women sharing the tasty fruits of Margot's labor. Soon, Margot was riding my cock as I brought Heather to a body shaking orgasm. She was a squirter and leaned back on my face to spray the other two as I lapped at her juices.
Margot was just getting warmed up as she pounded her hot cunt on me as fast and hard as her hips could move. I slammed against her hard enough to lift us both off the bed with each thrust. Margot started her deep moans and her nails dug into my chest as I relentlessly pounded her. Jacki was behind Margot, humping her and running her hands all over Margot as she neared her orgasm. She was cussing like a sailor as she and I ejaculated at the same time in a flood of hot sticky white lava. Both Heather and Jacki attacked the salty goo, licking hungrily at our genitals as Margot lifted herself off of me. Jacki slipped under Margot, sucking our cum out of her dripping cunt. Her deep tonguing of Margot made them both cum again. Heather engulfed my cock, sucking and licking me clean as my fingers rammed her ass and pussy. Heather quickly came again as her hand tightened it's grip on my cock.
Round one was now complete and we kind of just huddled up and collapsed in a mass of flesh and took a short nap as the sun warmed the swirling cool breeze.
The sound of Margot's phone woke us up. It was one of her biggest clients who showed up in town unexpectedly wanting to see investment properties. She hastily kissed each of us goodbye and hurried to clean up and leave.
"Howdy, the you-know-what is you-know-where." Margot said with another kiss. "Have fun kids, lock up when you leave!" she called, disappearing quickly into the house through the back door.
I snuggled in between Heather and Jacki as I felt Jacki's hand reach between my legs. Her sensuous touch had me hard again quickly. She was much more petite than Margot and could not get her mouth around my cock. She couldn't even stretch her vagina enough to take me without it being too painful. Believe me, I wanted to fuck this hot little slut.
Heather took control again and pushed Jacki onto her back and forcefully spread her legs. She slipped two fingers inside Jacki's pussy and started finger fucking her hard. I couldn't resist Heather's sweet cunt just inches from my face. I nibbled at her briefly before getting on my knees behind her. She easily took me deep as she ground her hips against me while she bent over to lick and suck at Jacki's hot cunt.
I had Heather's hips in my hands, ramming her hard from behind when we heard the back door open and Margot yelled out, "Hey you sluts, leave some dick for me. Muahs!"
Heather and Jacki both shot her the middle finger and laughed.
"By love!", Heather's sweet sexy voice called out. "Thanks for the little pool party."
Jacki flipped around, her face squarely under Heather and I as I fucked Heather. Jacki licked and sucked at our thrusting genitals and played with both us as Heather ate Jacki's pussy. The girls moans grew very loud and I knew I was about to cum again. As I shot my load in Heather, it dripped out her tight cunt. Jacki licked the treat as fast as it appeared around my shaft.
We decided to test Margot's theory about rolling directly off the bed into the pool. I went first and it worked. Heather and Jacki, still in the 69 position, laughed their cum squirting asses off as they finally rolled into the pool next to me. We played around a bit before calling it a day.
Margot had told me my money was in her panty drawer. So I slipped into her bedroom and into her massive dressing area. There, tucked inside the leg of a pair of red lace panties was twenty new Benjamin's. On top of the money was a hand written note.
"Howdy, thank you for cumming on short notice. I watched you through my window with the girls and it looks like you all hit it off great. Want to play with us again next week?"
I picked up her red panties, held them to my face and nose. She must have put them on, then rubbed her pussy with them prior to putting them back in the drawer. Her lovely woman scent was evident on the crotch. I held them in my hand as I masturbated in them, cumming in a big wad of sticky goo. Then I carefully placed them back in the drawer for her to find when she returned.
"Gypsy, are you ready?" I asked excitedly as she answered the phone.
"Ready for what? My surprise? Or to finish what we started earlier? she laughed.
"For all of it Gypsy! I have a quick stop to make on the way home. See you in about an hour."
My first stop took about thirty minutes. I already knew she loved it, because we had talked about getting one for a couple of months now. So I paid cash and told the guy where to deliver it and at what time. Then I made a visit to the florist to pick up the biggest fucking bouquet of red roses I could find. I tied a hand written love letter to one of the stems and placed the roses in the front seat of my BMW. I couldn't get back to Gypsy fast enough.
"Knock knock!" I yelled as I came in the back door holding her roses.
"Howdy? I can hear you, but I can't see you. Is that you behind that big ass rose bush you are carrying?" she laughed.
"Oh my God Howdy! They are beautiful." Here they came, tears streamed down her cheeks.
"I wish we had time to pick all the petals off one by one and cover the bed with them, but we have an appointment. Are you ready?" I asked nervously.
"Those are the most beautiful flowers I have ever seen Howdy. Thank you."
Gypsy kissed my cheek as she reached for my cock, whispered. "I'm going to fuck that cock of yours until it falls off tonight!"
We hopped in my BMW and headed for Jimmy Walkers, an upscale restaurant on the waterfront. It was a great restaurant right on the water with great atmosphere. We both loved seafood and steak, and JW's was one of the best.
We pulled into the parking lot and I hurried to get her door. I made small talk as we walked towards the front door. Right on queue, my present to Gypsy was waiting for it's new Cinderella. There in the front space by the front door, sat the 1963 split window Corvette Gypsy had said she wanted. It was Ermine white with red lipstick leather interior and a 327 power plant just waiting for her heavy foot.
Gypsy squealed loudly as she broke down sobbing. She held me closely as she wept.
"Don't you like it Gypsy?" I kidded her. "My gawwwd, what does it take to please you woman?" I taunted, working the crowd.
"Fuck dinner. I going to drive this bitch home and then I'm going to fuck you." she said loudly.
I turned to the crowd and apologized for not playing fairly. Most of them applauded as Gypsy slipped behind the wheel of her Vette. A turn of the key, and the deep throaty rumble of all 360 horses roared to life, making the ground shake around it. We left the BMW right where it sat and drove the long way home.
We drove down to Galveston and rode the ferry across the bay to Bolivar. Gypsy must have circled that Vette twenty times as the ferry chugged it's way across the bay. Every time she circled it, she threatened me with more sex. Then we drove nearly 75 miles out of the way the way before making it home over an hour later.
I don't know what I remember sounding better, the rumble of those side lake exhaust pipes dumping all that CO2, or the purr of Gypsy cumming over and over again as we fucked ourselves to sleep more than once, only to wake up and do it again.
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<a href="https://www.lushstories.com/stories/mature/confessions-of-a-boytoy-part-11-gypsy.aspx">Confessions of a BoyToy: Part 11, Gypsy Tells All</a>