The excitement of my graduation day from Winthrop was tempered by the realization I would be taking some very big steps in my journey to womanhood, very soon. My entire family, along with Diego, my former roommate Alicia and Alicia’s husband, William, attended the ceremonies. I decided to take the drive home with Diego.
During the drive Diego and I discussed our future together as well as my upcoming transition. A point of mild contention was where I would convalesce during post-surgeries.
“I really believe I should be at home. There will be four other women there to care for me, Diego,” I stated.
“I can agree to that. But what if I hired a nurse to care for you? I can also hire a housekeeper to clean, and a chef to cook for you. Your family runs a small business. They must be quite busy? They can always visit you. They need time to themselves, as do you. I ask you to think about it?” Diego said.
“I don’t need to think about it, Diego. I am your woman. If that is what you desire for me to do, I will do it,” I said smiling, realizing I would always obey his wishes.
My first surgical procedure was to be my bust implants. That would take place in the fall. I had turned twenty-one in March. I decided to move in with Diego soon after my Winthrop graduation. We would have the summer to adjust to each other, before my breast procedure.
Diego wanted me to have my own boudoir, “for privacy sake.” There I could nap if I wanted to, convalesce after my procedures, do my own hair, bathe, dress, do my makeup and keep all of my rapidly growing and fashionable wardrobe.
Of course, for lovemaking and sleeping most evenings, we would use Diego’s Master Suite. Lovingly, while I was still at school, Diego had a large storage space, next to my new, private boudoir, remodeled into a “Beauty room.” It was absolutely lovely and every “girly-girl’s” fantasy.
I now had a special room, with a massage table, a shampoo sink, a salon style set down hairdryer, as well as a hairstyling and makeup vanity. It was like having a small personal beauty salon of my very own, at my disposal. I was just so very in love with this thoughtful man. To me, any beauty salon is a feminine paradise.
Living with Diego as his concubine, was yet, even more wonderful than I could have possibly imagined. Waking in the morning with his strong, muscular and athletic body alongside of me was just an absolute dream come true. The scent of his musky, manly, taut frame would pleasurably fill my tiny nostrils.
I would reach over and inevitably he would have a raging, morning erection. He would stir as I gripped his fat penis. I would check the bedside alarm clock for the time and day. On any day he was scheduled to be at the pro shop and tennis courts, I liked to have his breakfast in front of him by 8 AM.
On those days, his staff arrived early, and he wasn’t due there until 10 AM. On his days off, Sunday and Monday, we took breakfast at his leisure. Once I ascertained that we had enough time to spare, I would slowly stroke his cock until I heard him sigh. Then, I would place his erect organ between my moist lips.
Often, I would take the time to coat my lips with my very favorite and wonderfully bright, luminous red, “cocksucker” lipstick. I loved the creamy taste it gave me when I transferred the lipstick to his erection. As I lovingly slurped his cock, I would watch his body relax. He was so very handsome when he was tranquil.
The greatest pleasure of my entire life will always come from making Diego happy and contented. I would continue to suck away. I always know from his body language when he is getting very close to one of his wonderful explosions. As his excitement grows, I increase my licking and slurping to the point that he finally erupts into my mouth.
When Diego ejaculates, I always suck and swallow every last drop of his strong, salty seed. This will always be my favorite method of saying, “Good morning my handsome love, Diego.”
Once Diego showers I ask him what he’d like for breakfast and I then mince to the kitchen to prepare it. I generally wear a negligee robe, marabou heels and fresh lipstick. I brush my hair until it shines. There are two things I never go anywhere without. High heels and fresh lipstick. I never want to be seen without either.
After I see Diego off to the country club tennis courts, I see to my housekeeping. A few hours before Diego returns from work I set my hair, so I have a new, fresh hairdo to greet him with. Besides a new hairdo and fresh makeup, I make certain he has a glass of wine or a Martini to enjoy when he returns home.
It was inevitable that our first summer living together would end. In early September I found myself undergoing breast augmentation surgery. I was going for a C-cup. Along with the hormones and T-blockers I was taking, I was hoping my breasts would develop into a very firm, D-cup.
I had already undergone lip-plumping collagen injections and permanently tattooed lip and eyebrow makeup at Gladys’ salon. My lips were now fat, puckered, bee-stung, “kiss me” lips with a nice soft, permanent rose shade. My sharply arched eyebrows were nearly non-existent except for the permanent soft, reddish dye that defined them.
The breast augmentation went well, and my recovery began. As he said he would, Diego hired a nurse, chef and housekeeper to care for me. The nurse was a stern, older female that paid wonderful attention of me. Mother, sister, auntie and cousin Laura visited to fawn over me.
My favorite visits though, were from Alicia, my former Cassandra roommate. Alicia had already undergone her full SRS process. Because Alicia had been through both the breast augmentation and the SRS procedures, my nurse trusted her with my care and would take an extended lunch break away from the house.
I envied Alicia so much when she showed me her new pussy. That wasn’t all she did though. I simply loved when Alicia would carefully massage my new, implanted breasts with Estrogen and Collagen creams.
She was so loving and caring. She would lay beside me. After a few soft, very special kisses to my lips, she would slowly massage either collagen or estrogen cream onto my news breasts. “Tell me when it is too much for you my pet. We don’t want to overdo it,” Alicia would warn.
“Oh, my, no, Alicia darling. Those velvety kisses and your lovely touch bring back such special memories of our lovemaking when we were roommates. I wish that I could do more for you. I’d love to put my mouth on your puss,” I said.
“Well then, maybe I should have you let me know when you are ready to go further. You know if your cock still works, even after all the hormones, we can always try that in my cunt,” Alicia sighed.
“Yes, that would be an idea, also. We could make these afternoons very special. What with our husbands at work and the nurse off on an extended break. Now that you are here, and we are in each other’s arms, we should make the best of it,” I agreed.
Two weeks into my recovery, the nurse’s schedule was changed to every other day. Alicia planned to come on alternate days, so we could be together privately. Our first day together without having to concern ourselves with the nurse, or Diego coming home for lunch, I met Alicia at the door. I was wearing a new, sexy, uplift bra, and had my negligee robe open.
I’d done my makeup as if I was going out on a date. My hair was “done,” and I was drenched in expensive French perfume. I wore a pair of sexy, “please fuck me” high-heels. I was ready for sex and so was Alicia.
“We need to do as much as we can honey. I’m scheduled for SRS after the New Year. So, this penis and my balls will be gone for good, baby. After that, whenever we sneak around and have some fun, we will only be able to suck each other’s pussies and maybe play around with a dildo or vibrator,” I laughed.
“Do you ever miss your penis or nuts, Alicia? I don’t think I’ll miss mine. Especially when I feel Diego’s hard cock between my pussy lips. Alicia. Do you think our men know we screw around with each other?” I sighed.
“Of course, they do. And I don’t think they would care at all. Not unless we screwed around with other men. By the way. You are correct about having a man’s cock in your vagina. It’s the most scrumptious feeling I’ve ever had. Having William inside my puss, made everything about my surgery, worth it,” Alicia said, gleefully.
“And don’t think Diego isn’t humping his rich-bitch tennis students. I know William is screwing all the nurses that fawn over him,” laughed Alicia.
“I know Diego bangs all the rich pussy at the country club, but it the long run it will pay off for us. I’m hoping, like William, Diego doesn’t propose until I have a new pussy. I want to have sex with him the same day he proposes. I want him in my puss for that. Not my butt,” I said.
“All this talk about men, pussies and screwing is making me horny girl. Come over here and kiss me,” ordered Alicia.
We kissed, and I slowly walked her into my boudoir.
As Alicia was always the aggressor in our lovemaking she pushed me to my bed. Then she removed my opened robe. She began to remove all of her clothing until she was in her bra panties and high heels. Smiling, she laid down on my bed and climbed on top of me.
Her kisses were forceful and aggressive. It brought back those lovely memories of being her roommate at the Winthrop school and how I was her “bitch” for much of the last half of the first school year. I can tell you now that if I wasn’t married to Diego I’d still love to be Alicia’s “bitch” any day.
She took hold of my penis while she sucked on my lips. Then, breaking from the kiss she said, “Why don’t we get into a nice ‘sixty-nine’ position honey? Then we can suck each other off.”
With Alicia’s pussy shoved into my face, she sucked my cock into her mouth. As usual, I was the “bottom,” but that was the way things will always be with Alicia and me. She’s a buxom, big bosomed, lusty lady. Compared to her I’m still the sissy “mommy’s girl” I was when I was her Winthrop roomie.
Alicia and I are great friends, but she will always dominate me whenever we are together sexually. She did a wonderful job, sucking my cock and it was really nice to eat her pussy. She was teasing me along and drawing out my lust. I thought she might have something else in mind and I was right.
I’d gotten her really high eating her pussy. She wanted my cock inside of her, with me laying on my back. As much as I wanted a pussy, just like Alicia’s, for the time being I was glad I still had my cock. This might be the last time I would ever have my penis inside of a puss.
I lubed up well, as did Alicia. She slowly lowered herself down upon my dick. Within a couple of months, I’d be so pumped up with hormones and into my ascent into womanhood, that I’d never be able to experience screwing from this perspective again. For now, I was going to enjoy my last piece of ass.
As soon as my cock was all the way up inside of her pussy, I began to thrust my hips towards Alicia. She in turn began to bounce up and down on my dick. We were both really into this action. I could see that Alicia had really learned to enjoy having a pussy.
Neither of us were going to last long, at this rate. Alicia was already pretty high from me eating her and I was way up there also from her having sucked my cock. Alicia went off first. As she humped up and down on me rapidly she grabbed her own breasts and squeezed her tit nipples. Just the sight of that was enough to set me off.
I began to pump my semen inside of her puss. It was very last time I would ever do that. I would soon have a pussy of my own and become as much of a female as a sissy like myself could possibly become.
After the New Year I went into the hospital to have my nuts sliced off and have what was left of my male organs used to help in constructing my new vagina. Upon my arrival home, Diego saw to it that I had all the health care professionals and servants I needed to recover.
Most helpful, because I always loved seeing her, was my dear fiend and ex-roommate Alicia. She was especially helpful showing me how to use the dilators to keep my pussy opened. I wanted to be ready for Diego one day. During those visits William came and he and Diego, due to a common bond they had, became fast friends.
Once I had recovered, Diego and I would double date with William and Alicia. One evening, the four of us went to the country club for dining and dancing. During a slow dance William and Alicia got up and went out on the dance floor. I was disappointed that Diego didn’t ask me to dance.
Disappointed only until I saw him open a box that contained a diamond engagement ring! “Will you marry me, Babette Cheree Chambers?” Diego smiled.
I couldn’t help myself. I got up and walked around the table to the other side and stood in front of him. I extended my left hand. I was crying so girlishly. I wiggled my fingers and he slid the band onto my ring finger. Then he got up and propelled me onto the dance floor.
I had almost stopped crying when I finally said, “Yes, I’ll marry you Diego. I’ll be thrilled to be called Mrs. Iglesias.”
The wedding was very traditional. Diego’s family flew over from Spain. His brother was his best man and William was one of the groomsmen. Mother gave me away. My sister was my maid of honor. My cousin, aunt and Alicia were bridesmaids. We honeymooned in Cabo San Lucas.
We finally bought a house in the country club where Diego is still the top Tennis Pro. The other day we began discussing adoption. All Diego’s family knows is that for some reason, we can’t have children.
The Dénouement
Once a year, Diego and I celebrate our wedding anniversary in Cabo San Lucas where we honeymooned. After the first year we decided to rent a bigger house and invite Alicia and William to accompany us. That has been going on for five years.
Alicia and I are closer today than we’ve ever been. One afternoon we discussed it and thought it was only right to be completely up front and tell our men that we knew of their philandering, but we didn’t mind at all, as long as they came back to us.
Unbelievably enough both William and Diego acted surprised that we knew and were even more surprised we were so cool about it. The last time we were in Cabo together, we were sitting around relaxing when it came up, sort of.
We’d all had a few drinks after going to the beach. Everyone had showered. The men were in casual shorts, tank tops and sandals. Alicia and I, being really risqué, were dressed in panties, shorty, negligee style robes and high heeled slippers. We’d done our makeup and blown our hair dry.
We had just lit a joint of Mexican weed, when Alicia teased William about looking at all the hot pussy on the beach that day. I laughed and said I’d caught Diego doing the same thing.
We were all laughing when William asked Alicia, “So you never looked at men on the beach?”
“No, I never look at men anywhere. Now, staring at hot looking women would be another story,” Alicia teased.
“What about you Babette? You like looking at good looking men. Don’t you?” Diego asked.
“Honey, I’m more like Alicia. I kind of like looking at tight asses on females,” I smiled.
“I’ll bet these two get together when they visit each other and we’re at work or on the golf course Diego? How about it Alicia?” William asked.
“Let’s see. Well, yes. Babette and I got it on all the time when we were roommates at Winthrop. And once Babette had gotten over her boob job, we made out a few times. But you know, I haven’t been with Babette since she got her new pussy. Now that would be fun,” Alicia added, upping the ante to somewhere I didn’t want it to go.
“Alicia, stop. We’re all just kidding around here. That might be a little too much information right now?” I said, looking around the room.
Strangely enough, neither Diego or William seemed overly concerned about anything Alicia had just said. In fact, they both looked kind of intrigued.
“You’re still the little Mommy’s girl, aren’t you Babette. I think that Diego as well as William, might want to know if I’m kidding about all this. I’m not Babette. I’d like to taste that new pussy of yours’. And, I think the men might like to see that show. So, boys would you like to see a little bit of Lezzie action?” Alicia asked as I turned red in the face.
Both Diego and William just shrugged, smiled casually, passed the joint of weed and sat back on the comfortable living room chairs. I looked at Alicia and she crooked her finger at me, smiling.
“Come over here, bitch. You’ve been my bitch since your first year at Winthrop. And you’ll never stop being my bitch, Babette. Now get over here and sit next to Momma Alicia,” she ordered.
I got up with my hand covering my lips. It was so weird, I was high as a kite. The only words I could say as I walked over to her, were, “Alicia, no. Not now. Please?” I whimpered but I kept walking right up to her and sat down on the couch next to her.
“Yes. Now honey,” was all she said as she leaned over and gave me a very sensual, truly hungry French kiss.
Then the action really began. She opened my robe and began to nibble, suck and kiss both of my tits, one after the other. The only thing I heard from either Diego or William was, “Oh, wow!”
Alicia was all over me. She couldn’t stop, and now, neither could I. I reached into her panties and started fingering her pussy. At long last we were on the floor, with me on top and Alicia on the bottom, eating each other’s cunts. We were both panting like crazy when Alicia gasped, “Boys. Want to join in?”
“Sort of. This has really turned me on. I’d like to take Babette to bed with me,” laughed Diego walking over to us and taking my hand.
I was truly embarrassed, but he pulled me to him and said, “That was great. You two need to do that again.”
On our way to the bedroom I heard Alicia and William laughing, likely on the way to their bed. When Diego shut our bedroom door I grabbed his cock, pulled him to the bed on top of me and began guiding his penis inside of me.
“Diego my handsome stud, please fuck me?” I said.
And he did.
The End
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