Dinner at Diego’s was lovely. It turned out just as I had hoped. We were sitting in Diego’s remarkably decorated living room, having coffee and desert, when Diego spoke to my mother. “Ms. Chambers, I would like to ask your permission to see your daughter, Babette, socially, for some dates? I hope I can get your permission? I am an old school Castilian, and as she isn’t twenty-one yet, I insist on asking you,” Diego said.
“Well first, Diego I insist you call me Deidre. Yes, of course you and Babette may date. Babette will be twenty-one in the spring. Babette. Is that what you want? Would you enjoy dating Diego and be his girlfriend?” Mother asked as I blushed.
“Yes, Mommy, I would love that very much. Now all Diego has to do is ask me for a date,” I teased as I thrust my boobs outward.
“Well then, I am very happy. Babette, would you honor me by having lunch at the Bay Colony Club, next Saturday at 1 PM?” Diego smiled as I accepted.
Mother had asked that I not dress as if I were some sort of slut for the luncheon date. I simply could not help myself, though. One of the first things I did after taking a hot bubble-bath, was to fully moisturize my body. I’d slept with my butt plug in my rectum. Now that it was removed, I inserted the applicator end of a tube of KY-jelly into my anal canal.
I squeezed a generous portion of jelly into my anus. I wanted to be ready for sex if Diego desired me. I was going to make certain he did want me sexually. I inserted a small tampon inside me to hold in the lubricant. I put the applicator tube in my purse. I would be sure to lube Diego’s cock when appropriate.
I put on a panty brief but without a gaff. I wasn’t that concerned about getting an erection in the restaurant. Though I did add a sanitary napkin just in the case my penis might ooze some sperm. I decided to wear white, patterned opaque hose, to emphasize my gorgeous legs. I slipped into a white tube top. Then a decorative, abstract patterned, navy, pencil slim midi-skirt.
The pair of four and a half inch, triple-strap, white, high-heeled sandals would be the kicker. They made my legs look fabulous and helped me to thrust my boobs out even further than normal. I blew my long, medium-shade, auburn locks dry, and styled them sleekly using a gel. My tresses looked so shiny.
I spared nothing with my vivid makeup or my heavy perfume. Gladys had told me of a new, French scent, that all the Bay Area lesbians were using. It was called “Sapphic Ardor.” I applied it heavily. I made certain my mascara was thick and lush. I did the same with my exceptionally wet, “Ruby Flame” lipstick.
I was ready to entice my man. I checked my new wristwatch and minced down the stairway to the parlor. My mother looked up and shook her head. Then she shrugged. We lived in an elegant, restored Victorian. I felt like one of those girls in a romance novel.
“Well, you’ve left very little to the imagination, and you won’t have him guessing, will you? There he is now, pulling into the drive. Try not to run to the car and jump into his arms. At least let him come to the porch. Oh my. You have a wonderful time Babette,” mother sighed as I sashayed out the door.
‘Yes, mother. I will. Please don’t wait up. I’ll call if I decide to spend the night at Diego’s,” I said flirtatiously. I didn’t want her to doubt at all what my plans were for this first date.
I felt like I could stop traffic. I know Diego slowed his walk when he saw me. He recovered well and smiled. I met him in the walk way to our house.
“You look very lovely Babette. Come. Take my arm. Please let me get the car door for you,” Diego said so elegantly.
I was quite excited about being with this famous man at such a sophisticated place as the Bay Colony Club. I could hear the buzz and babble of the Saturday lunch crowd when Diego walked in. He didn’t live in the Colony Club development, but as the club tennis pro, along with his wealth and fame, he rated a membership.
Casually glancing around, I could see a number of people, males and females alike, looking our way. I also noted Diego nodding, acknowledging and smiling at a few of the people who were staring at us. Back then I had not a clue that he was screwing a substantial portion of his female tennis students.
“It appears you know a number of the people having lunch here?” I inquired.
“Well, yes. Many of the women and only a few of the men are my tennis students. That takes up much of my job here, as the pro. I just might retire from World Tennis altogether. I’m very well off. I still have a number of endorsements, thriving investments and this job is satisfying enough,” he said.
“I’ll miss a lot of the excitement of the tennis circuit, but I’ll still attend matches as a celebrity guest. I actually enjoy golfing now. I’m not good enough to be a pro, but I appreciate appearing as a spectator at the major tournaments,” he added.
I wanted badly to play the role of the submissive female to the hilt. So, when the waiter brought the wine and drink list, along with the menu, I set the menu down.
“Diego, would you mind terribly ordering the beverages as well as my lunch for me? You know the menu so much better than I do. Please keep in mind I’m watching my waistline as I adore keeping my figure girlishly slim. I just feel so much better about myself when I’m slender,” I giggled naughtily.
Diego passed on the wine, and instead, ordered both of us a cocktail. He was so sweet, ordering me a light lunch and honoring my request. He looked up and down my figure smiling. Midway thru the meal I asked for a second cocktail and he complied. Shortly after, he asked if I would like to take a drive somewhere, after lunch?
“Yes. I do hope you don’t find me to be too very forward? I’d love to drive over to your house and see what your bedroom looks like? I’ve heard you’ve had your share of famous women there. Would you like to take me to your boudoir, Diego?” I asked, pouting my lips and putting my hand on his arm.
He raised his eyebrows at my remark. Then he put a hand over mine. Smiling, he said, “I have only recently purchased this home. I have yet to have a lady into this bedroom. However, if you would truly like to see it, I would love for you to be the first, Babette.”
“Well then. I suggest we complete our lunch. Because I am absolutely yearning to get into bed with you, you very adorable man,” I whispered into his ear, huskily.
By the time we were in Diego’s vehicle I could see from the lump in his pants, that he already had an erection. I couldn’t resist, reaching over and rubbing it. I know my penis was already leaking fluid. For the first time, I wished it was my pussy that was dripping and oozing.
Diego glanced over at me and commented, “You look slightly different than at dinner last Saturday. I can’t put my finger on what it could be?”
“I’m wearing more makeup, for one. And, my hair isn’t curled. I blew it out straight and sleek. Just for you. Thank you for noticing darling,” I said, leaning over and pecking him on his cheek.
“Well, you are most stunning today, Babette. And you were as equally lovely last Saturday. Please do not think I am being rude. When I look at you, I cannot possibly envision you as ever being a boy. I cannot fathom that. You are much too beautiful as a female,” he said, tenderly.
“Darling, I hope you can never picture me as a boy. And it is so very, very charming of you to say that. I never want to be a boy again. That person is gone forever. And though I am still partly a boy, I only desire to flourish as a more feminine person as time passes,” I smiled.
When we arrived at Diego’s home, I asked him to bring a bottle of wine to the bedroom. He paused and said, “I am not certain I want to bring you home with too much alcohol on your breath, Babette?”
“Don’t worry. If all goes the way I would like it to, you won’t be bringing me home at all until Sunday afternoon. Which way is your boudoir Diego? I want to get my clothing off. Then we’re going to get you undressed,” I purred.
Diego pointed the way to his bedroom. By the time he’d uncorked the wine, put it into an ice bucket, and arrived at his room, I was standing nearly naked, in panties and high heels, next to his bed. I had removed the tampon plug from my rectum and the napkin from my panty.
When Diego sat the ice bucket down, I began to unbutton his shirt and I took it off for him. Untying his shoes, I helped him to get unshod, before I unzipped his pants. Once his underwear was removed, I knelt in front of him, adoring his erect penis. First, I fondled it lovingly. Then I kissed the tip, while I lightly played with his balls. Next, I took his testicles very gently into my puckered lips.
Lastly, I took as much of his massive penis, as I could manage, into my mouth. I began sucking, eagerly. I had of course, sucked the cock of my Winthrop roommate, Alicia. Face it. Like me, Alicia had a sissy cock. Diego’s cock was the penis of a very masculine, manly male.
It was huge. I wanted to suck it, until he shot sperm into the back of my throat. Then I wanted to get it rock hard all over again and have it shoved up into my greasy, well-lubricated ass. Diego’s massive manly penis came beautifully to life.
It swelled in my mouth. He showed his appreciation and fervor, by stroking the sides of my face and running his strong hands through my auburn tresses. As much as I wanted him to shoot his load into my mouth, he had other ideas. And if my loving man ever wants something of me, I respond dutifully.
“Babette, my angel. I want to be inside of you, my lovely. Please kneel on the bed, my princess,” Diego politely stated. Diego is always very polite whenever he wants something. Of course, he knows I will comply with his wishes instantly.
I wanted him to know a few things immediately. I wanted him very aware of how I saw our relationship, as well as my perceived place in the bond. “Yes, of course my dear Master. I am your devoted love slave and I shall continually revere all of your commands by my prompt submission,” I consented.
On my way to kneeling on the bed, I took the lubricant tube from my hand bag. I first knelt facing Diego, who was standing at the foot of the bed. His rock-hard male organ was in his hand. I generously rubbed the lubricant all over his swollen penis. He climbed upon the bed. Just before I turned my ass to him I put a bit more lube up my butt.
On all fours, I stuck my behind up invitingly as a love offering. I felt Diego’s strong hands position me perfectly for him. Then as he rocked me back and forth he slowly, gently and carefully entered my anus. He was such a superb lover. Any girl would give her all to have this man make love to her.
I felt so fortunate to have this wonderful masculine male screwing me. It was true, that Alicia had made a real girl out of me. Now, Diego was about to make me into as much of a woman as I would ever be, without me actually having a pussy. His penis entered further and further into me.
I gasped, sighed and whimpered. But I begged for him to go further. “Enter me my Master and make me your woman, your concubine and your slave-girl. Please, screw me so I will know for certain that I fully belong to you and only to you?” I pleaded.
And screw me he did. When his large, eight-inch long cock was fully inside me, I again knew the feeling of bliss that occurred when a penis contacted my prostate. As he rocked his penis in and out of me, I emitted little squeals of delicious delight. My penis also grew and stood out straight, belying my gorgeous girlish appearance.
I moaned enjoyably, as I approached my nirvana. I truly felt so enraptured with this masterful Adonis. He’d made me feel like I’d never felt before in my life. If this was even close to experiencing the gratification a sated woman might know, I wanted so much more of it.
When my cock finally spurted, my overtly effeminate shrieking became nearly frenetic. I gasped, as sweat and tears of yearning poured off my face. I was beside myself with jubilant exhilaration. In spite of my prodigious climax, I held my buttocks as steady as I could. My concern was that my man, Diego should have the same moving orgasm that I had experienced.
Very soon he did. Pounding my rectum for all he was worth. Then I heard such a very manly grunt escape from Diego. He then began to pump his moist, warm semen into my anus. The feeling which I received from his ejaculation was simply thrilling. I only wished it were possible for me to become impregnated with his beautiful offspring.
For now, I would have to be satisfied that he had paid me the grand honor of making love with me. I mewled in effeminate contentment. As Diego took his dick out of my ass I turned and smiled seductively at him. He laid down on the bed with a fully satisfied glint in his eyes. I laid next to him, on my side and kissed him.
I moved my hands across his chest and kissed his nipples playfully. I climbed on top of him and kissed his face and eyelids. I didn’t want to lay on my back as I wanted to keep his sperm inside of me. At long last I kissed him and said, “Let me get something to clean off your penis, love?”
I went into his bathroom, with my panties and purse. I sat on the toilet and flexed my butt cheeks. Diego’s sperm flowed freely from my asshole. I inserted a slightly lubed Tampon and put my panties back on. I returned to the bedroom with a warm washcloth to clean off Diego’s cock. Then I laid beside him, demurely and cuddled myself to him.
“Darling, I would love to stay with you the weekend if you’ll have me? I want to cook for you and clean your house and provide you with plenty of hot, steamy sex. Only if you want me here though. If you want me to leave, I’ll understand my love,” I whispered.
“Of course, you may stay here with me. As long as your mother knows where you are. But you didn’t bring any extra clothes. Therefore, we’ll have to take you shopping, before the stores close. Where do you like to shop? I would love to get you some clothing you could keep here for impromptu evening and weekend stays. Plus, you’ll need to get things that ladies use for their hair and face,” Diego stated.
I called mother, to tell her of my plans, on the way over to “Elaine’s” boutique. It was fun shopping for outfits there and playing the role of sexy, model girlfriend for Diego. He also took me to Gladys’ salon where I purchased makeup and hair care products. I cooked a late supper for us and cleaned the kitchen immaculately.
I then gave Diego a hot bath. While he was in the tub I gave him a very sensual blow job. After a shower, I put on some of the lovely sleepwear we had purchased at Elaine’s before going to bed with him. The excitement of that summer, as Diego Iglesias’s girlfriend had hardly begun.
A week later Diego asked me to accompany him to the US Open Golf Tournament at Pebble Beach, California. It was to be our first public appearance together. Diego took the time to discuss any press releases from his agent, with both mother and Lydia Faberge. It didn’t take long for the publicity to begin.
Our first day on the course, as part of the entourage accompanying last year’s champion, we saw a few photographers taking shots of Diego and I together. I wore a navy on white, sleeveless, polka dot mini-dress, with wedge-heeled sandals. My hair was pinned up, and I wore sunglasses. Thick red lipstick adorned my lips.
That evening my mother called me, saying she had watched one of those gossip shows, and they were asking, “Now, who was the mystery young lady with Diego Iglesias at Pebble Beach?”
The next day, Diego’s agent released a statement identifying me as, “Babette Chambers, 20, of Hillsborough, California. Babette is the daughter of Deidre Chambers, co-owner of Chambers Décor, also in Hillsborough. Babette will be a sophomore, this September, at Winthrop Academy, a private girl’s finishing school in Mendocino. She plans on working as a receptionist and secretary for her mother upon graduation.”
Later that day, one of the gossip columnists wrote a story, which began with the headline, “Is Diego Iglesias robbing the cradle?”
Of course, Diego and I had a good laugh over that one. If they only knew. That Saturday, the third day of the tournament, I experienced my first mini-interview by a reporter accompanied by a TV camera. The reporter, Angie Weldon, was an attractive female, who couldn’t seem to take her eyes off of my hunky man the entire time she quizzed me.
Reporter: “So Babette, how long have you and Diego been seeing each other?”
“It has only been a few weeks Angie. We met, thru a friend, right after summer vacation began,” I answered, lightly fingering my bobbed hair.
“So, what do you think of all the excitement of the US Open?” Angie asked.
“There certainly is quite a bit of glitz, glamour and enthusiasm here. Really though, my main focus is enjoying myself, just being with this truly marvelous man,” I smiled, leaning against Diego and clutching his arm possessively.
“Oh, now that says a lot to me. And yes, marvelous is an excellent description of Diego Iglesias isn’t it, Babette? So, any plans between the two of you?” Angie asked nosily.
“Only to enjoy the rest of this gorgeous day and the rest of the tourney. If you’ll excuse us Angie, we want to get back with the rest of the gallery,” I said.
Even more exciting was the next trip we took, to Las Vegas for the Barracuda Championship. By then, mother had been interviewed leaving work, and the press had also spoken to Lydia Faberge, the headmistress at Winthrop. Lydia did have to field several phone calls from mother’s wanting to enroll their daughters at Winthrop. Of course, Lydia had to explain that she was at full enrollment.
When the summer did come to an end, I returned to Winthrop for my second and last year. I did have plans. I wanted to have bust improvement implants. I also wanted to begin counseling for the final surgery. I discussed everything with my aunt, mother and Diego. It was decided I wouldn’t be doing anything in the way of surgeries until after my graduation from Winthrop.
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