Fulfilled by Gingerfred Man
Chapter One -- The Letter
I was sitting at my desk at work and trembling as I read the letter for the third time.
"Dear Mr. Harris:
"An anonymous benefactor has arranged for an all-expenses-paid, two-week vacation for you at `Fulfillment'," our tgirl fantasy spa in the Mediterranean island country of Gingerfredonia.
"Your dream experience will begin on July 24. A general description of optional activities is enclosed. No need to make your activity selections now. There will be plenty of time for that at our lovely facility.
"A list of items you may wish to bring is enclosed as well, but everything you will need is, of course, available and free of charge at Fulfillment."
The letter went on to give details of my first-class travel arrangements to the spa.
It was everything I had ever dreamed of. And my worst fears confirmed.
I had been "dressing" since I was twelve and enjoyed nothing more. In the twelve years since, I had never ventured out and was sure that absolutely no one knew of my secret needs and desires.
But someone knew.
Someone either kind enough or cruel enough to allow me to fulfill my deepest desires. Someone who remained anonymous for reasons of his or her own. To tease and torment me? Or make me deliriously, blissfully happy?
My name is Grant Harris, but in my fantasy world, I'm Tiffany.
Tiffany is a feminine treasure, to be prized by the many potential admirers of her beauty who would surely be overtaken with desire for her if they only knew she existed.
Only I had seen her. Had become her. Two or three times a week when I was living with my parents. Five or six times a week since I graduated from college, began working at an accounting firm, and got my own apartment.
I often thought that Mom and Dad knew, or at least suspected. They never came home unexpectedly or visited me at my apartment without calling first. It was as if they knew there was something they didn't want to discover, so they avoided it. Not so unusual, I guess.
I knew Mom and Dad thought it odd that I never dated. I didn't feel I wanted to date anyone as Grant. Tiffany had very specific and hungry needs, but Tiffany was a recluse.
By the time I was 21, I thought Mom and Dad half-expected me to say I was gay. I thought they would have been relieved in a way. Sexlessness seemed very sad to them.
Grant was a sexless blob. Small, thin and fit and not bad looking. But with very little personality and no interest in women or men.
Au contraire, Tiffany had intense, vivid desires that drove her to bring herself to cataclysmic, multiple orgasms, emptying her pretty balls and taking her breath away.
Things became critical and almost disastrous for me in high school when I had the biggest crush on my best friend, Bill Emory.
Bill was sweet and handsome and lovable and hunky and we told each other everything. Everything that didn't matter.
I would lie in bed at night and dream of Bill and Tiffany at the prom. I would be wearing a magical silver dress and high-heeled, sliver sandals and Bill, in his tux, would be whirling me around the dance floor, my long, blonde (of course) hair flying as he romanced me for all to see.
In my dream, I was an angel of love for Bill. I would stroke my little doodle as I dreamed of Bill bringing me home from the prom, taking me to my room and stripping me, clothing-article by clothing-article. He would kiss each area of skin he exposed, of course, and I would gasp and pant with passion. In my dream, I had big, luscious titties and Bill would lick and suck them, driving me wild, both in the dream and in real life. I would usually cum from imagining Bill adoring my nipples, then cum again as I thought of him eating my dream pussy. The residue of two cums would cover my belly as I imagined Bill on top of me, fucking my pussy as he praised my beauty. And pushed his big cock in and out of me. I couldn't escape. Being fucked on my back was my girlish destiny. And, pretending I was fucked and helpless, I would cum again for the third time.
The reality was kind of sad. Bill went to the real prom with Angela Turner and I stayed home and watched a Beavis and Butthead marathon. (Uh...huh, huh...huh)
Then Bill and I went to different colleges and hardly saw each other again.
What would Bill have done if he knew about Tiffany? I was sure it would have involved welts and loss of blood for me.
No one could ever know about Tiffany.
But someone knew. How? Who? And what did that someone want in return for my very expensive trip to the Fulfillment spa?
There were 300 people in my firm, Ricardo, Mertz & MacGillicuddy. Grant wasn't very social, so I only knew about 30 of them. The letter about Fulfillment was sitting on my desk and had been hand-delivered without postmark.
So it was one of them. Or not. Someone else could have paid a delivery person to confuse me. Unlikely. I was sure it was one of them.
But who was it? A man or a woman? Someone with money. I had heard of Fulfillment. It was like those baseball fantasy camps that middle-aged guys go to. They dress like ballplayers and play some games with old major-leaguers. But Fulfillment was supposed to be top-of-the-line. Expensive. It was in the country that crazy TG-fiction author Fred Gingerman had bought a few years ago, set himself up as king and pulled off an economic miracle.
My firm had been around since the early fifties and its founders had died in the 80s and 90s. It was being run by the Ricardo's son, Richard, Junior, who was still called Little Ricky by the old timers. Could it be him? I doubted it. He spent a lot of time on his bongos and very little time at the office.
Should I go?
I had to. Tiffany needed it. She needed to breathe free. And I needed to find out who my "benefactor" was.
I filled out a Ricardo, Mertz & MacGillicuddy form requesting my two weeks vacation for the time at Fulfillment. Terror and excitement are a heady combination.
Chapter Two -- Checking In
Though I wavered about going, Grant showed up to board the plane to Gingerfredonia and I flew in fine style to the fast-developing nation's capital of Santa Femina. A limo awaited me and I was whisked to the seaside spa, which was less than an hour from the airport.
It was lovely. Each guest had a separate, one-bedroom villa. The staff was helpful and polite.
My room had all the feminine necessities and luxuries Tiffany would need. A huge closet was filled with clothes and shoes and lingerie -- all in my size and in varying degrees of sluttiness -- from church lady to crack whore.
I sneaked little peeks at the other arriving guests and found them to be much like me in appearance and shyness.
Shy or not, Tiffany was about to make her first public appearance.
Just as I was deciding what to do next, there was a rap on my door. Still dressed as Grant, I answered to find a late-30-something, handsome man in a fine Italian suit.
The gentleman bowed and said, "Good evening Miss Harris, I trust all is to your liking so far?"
MISS Harris? Very nice. "Yes, thank you."
The gentleman smiled. "Wonderful, Madame! My name is Gianfranco and I will be your personal concierge for your stay with us. If there is anything you need. Anything. I will arrange it for you."
I blushed. Surely he didn't mean... Of course not. "Thank you," I said.
He smiled warmly and produced a small catalog. "This is a list of the activities we offer tomorrow. Each day I will bring you a new one. You'll note that they are rated by G, PG, R, and X. Just like your American films once were. We ask that you select at least one following-day's activity before midnight each night. Just call the operator. Please. Or call me if you wish to discuss it or arrange it. You'll want to dress appropriately for the activity, of course. I'm eager to see you in your feminine clothes. I'm sure you're very beautiful."
That flatterer! I blushed a little. Or Tiffany blushed. I was dressed like Grant, but Tiffany was pushing to get out.
"If I may recommend, Miss Harris, select an activity, order a meal in, then get into a pretty nightie and go to bed early. Jet lag will get you if you don't and you'll need a lot of energy here."
My cock was hard just thinking about it. Tiffany was a trampy little man pleaser who wanted to suck cocks and take them all the way into her pretty bottom. In her mind, at least. She'd never touched someone's cock and had never had an orgasm with another person. That was about to end.
In fact, Tiffany was thinking how nice it would be to suck down Gianfranco's cum right about then. But before I knew it, he was gone.
I decided to become Tiffany before I did anything else. I took a long, hot soak in the huge tub, shaved my legs and other intimate areas, and perfumed and powdered myself to perfection. I styled my long, usually pony-tailed hair to a brunette crown. I made my face into the lovely Tiffany I had come to adore. Then I put on pink stockings, with a matching garter belt, pink, fluffy, stiletto mules, and a lovely, brief pink nightie that completed my ensemble.
I thought about calling Gianfranco and telling him there was something I needed right then -- big and hot and hard. But as usual, I was a chicken.
The first person to ever view Tiffany turned out to be the waiter who brought my dinner, salad greens with lemon and ice water. Either he was a great actor or that bulge in his pants was appreciation for my femmy side.
As I ate, I scanned the catalog. The G stuff was awful -- a visit to a nail salon. Shopping for clothes in the Gingerfredonia Frumperia. Ick.
I blew by the PG and R stuff too and made my choice from the X-files. I read the description and called in "After School Date."
Jet lag caught me and I lay in all my beauty in the huge bed and dreamed of losing my virginity. The sooner the better.
Chapter Three -- First Fantasy
The description in the catalog recommended dressing like a high school girl for "After School Date."
I wore a very short, plaid, pleated skirt, tan stockings, white garter belt, black, three-inch-stiletto sandals, a white blouse and lots of lipstick, perfume and eye make-up. I looked like the girl I wanted to be in high school. Pretty, trashy and popular.
As I was admiring myself, I heard a knock on my door. It was Gianfranco.
His eyes bugged when he saw me. I do make a very sexy girl. Great legs. Girlish mannerisms. Pretty face. I was very pleased.
"You're very beautiful, Miss Harris," he said. And his lumpy crotch echoed his sentiments.
"Thank you, Gianfranco, but please call me Tiffany."
"Of course, Miss Tiffany. Have you breakfasted?"
I had eaten my Special K, skim milk and black coffee an hour earlier. "Yes, thank you," I replied.
He smiled. "Let me tell you about this activity. It will begin in a high-school classroom. One of these boys, whichever you choose, will take you home after school. Your parents work, so you will be alone. You and the boy can do as much or as little as you wish. Much of each activity is up to you. Now remember, you can stop any activity by saying your safe word. Do you remember it?"
I did. "Skywalker," I said. I was a Star Wars fan, OK?
"Right. Everyone in the spa knows that word means stop whatever is going on and take you immediately back to your villa. I would recommend that you use it only out of necessity. Otherwise, you will miss a lot of the fun."
I shivered a little at that. I wondered if the sissies at the Nail Salon fantasy would use their safe words if the polish was the wrong color.
"Please select one of these boys. Each is 18, six years younger than you, and very nice and sweet. And hot for your teenage body. In the activity, you're 18 as well."
I looked at four studly Mediterranean lads and picked one almost at random.
Gianfranco nodded. "Angelo. Good choice."
So Angelo would have my pretty bottom! Mmmmm. I was scared, but couldn't wait.
Gianfranco took me to a building that could have been a school. There were about fifteen 18-year-old boys, and girls in there, and a teacher. I spotted Angelo, who was in the same row as I was, to my left. He was smiling at me. Nice smile. The teacher droned on about something for about ten minutes, then a bell rang.
I could feel the mood. It was like high school. Where I could have been a very popular girl. If I had had the stones to dress full time and say "screw it" to the world.
But this was a second chance.
I got up and walked out of the room. Angelo ran to catch up.
"Hi, Tiffany," the very good actor said. "Can I walk you home?"
Should I say `Skywalker' get on the next plane home and go find Miss Right and marry her?
Uh uh.
"Sure, Angelo."
Angelo carried my books and chattered happily about a lot of classmates and teachers I didn't know. He also took plenty of time to praise my beauty, about which, he seemed sincere.
Unless my mirror was lying, I was beautiful. I stopped to fix my lipstick. Just in case. Angelo watched me with interest and I thought I could see a bulge in his trousers as well. I was three for three in erections!
It was wonderful being among people as Tiffany. I knew that it was a controlled situation, not the real thing, but I was gathering the courage to step out as Tiffany in my real life.
Angelo was so sweet. When we got to what I guessed was supposed to be my house, I reached in my purse and pulled out a key that Gianfranco had given me. It opened the door. I entered and invited Angelo in. He laid my books on a table.
He was young, but very handsome. Not too young. I was only 24. He smelled very good. And I was very hard and throbbing in my panties.
He stood facing me and moved an inch away. My knees were shaking a little.
And then he kissed me.
My first kiss. It was the most erotic moment of my life.
The wonderful boy held me in his strong arms and kissed me deeply and exquisitely. I was trembling with lust as he entered my mouth with his wet tongue. He cupped my soft bottom with his hands as we kissed and kissed.
I was such an ingénue. I just let Angelo lead.
My cock was crowding my panties terribly until, , Angelo reached into my panties and freed my throbbing cock. No one had ever touched it before. I was in heaven. He was kissing me and stroking my cock and all of a sudden, I squealed and began cumming. Spurt after spurt of my sticky cream leaped from my delighted cock.
Oh. It was already the best day of my life as I felt my balls draining all over my "parents'" rug.
Should I return the favor? I did Angelo one better. I fell to my knees and squealing happily, pulled down his pants and held his perfect cock in my warm hand. Angelo moaned manfully.
I skinned his foreskin back and kissed the pink tip.
"So good," he moaned.
I had never even touched anyone's cock. It was wonderful! Hot and hard, but velvety smooth, just as I had imagined. I began to orally adore that fine specimen. I jiggled his balls as I kissed and licked and sucked Angelo's slippery knob.
I was a cocksucker at last!! I would have to amend my resume immediately, I mused, as I brought poor Angelo to a fever pitch. Without warning, the bad boy fired glob after sticky glob of hot cum all over my pretty face. That was OK. He was really enjoying himself. I could get a towel or something. I wondered what Angelo would do next.
Then I looked in Angelo's eyes and saw...FEAR!
He was looking behind me at the front door. Then he said, "Oh no, your father!"
What? I thought we were going upstairs and Angelo was going to put his big thing into me. This wasn't supposed to happen. Or was it?
I turned and saw a very angry looking...Gianfranco!!!
He was playing my father in this activity?
"TIFFANY! You little tramp! I told you about this before. Angelo! Get out. I'll deal with you later."
Angelo picked his pants up and, without even saying goodbye to me, he ran out. The coward. I didn't like the way it was going, but I decided to play along. "It's not what you think, Daddy," I said.
Gianfranco or "Daddy" was angry. "What was it, then, Tiffany? You were eating birthday cake with Angelo and that's his `icing' all over your face?"
He was right. A face full of cum and a boy's cock in your mouth are difficult to explain. I didn't say "Skywalker," but I took the sissy approach. I began to cry and apologize. "I'm sorry, Daddy. It just happened. I'll never do it again!"
I knew that no Daddy could resist a daughter's tears. I was wrong.
He said, in a low and threatening tone, "You're getting a spanking, young lady."
He was kidding, right?
"Daddy" sat in a hard chair and said, "Come over here, Tiffany."
My safe word was on the tip of my tongue. But I didn't want to look like a wimp to Gianfranco. And my cock was severely erect and excited at the prospect of what was about to happen.
Reluctantly, I tottered over to Daddy. He handled me roughly, pulling down my panties, and seating me on his lap for a pre-spanking lecture.
"You're going to get it very badly this time, Tiffany. I know that all the boys want you because you're the prettiest girl in school. And I know they all want to suck your big stiffie and have you suck theirs." He was massaging my cock and balls most deliciously as he spoke. "But you're too young yet." I was close to cumming and wanted to kiss him very much.
Abruptly, Daddy stopped stroking me. "Oh no, Missy. You're getting a trick, not a treat."
I was so hot and aroused. And unfulfilled. Daddy placed me across his knees and turned up my skirt. My pink, bare bottom, thighs and balls were open and horribly exposed.
I was scared. And aroused. Daddy had trapped my stiff cock between his thighs and the friction was rubbing it nicely. Ohhhhh.
But the fun ended quickly. Daddy's hand stung my left bottom cheek. I screamed as if I had been shot. I didn't think he would actually spank me! Another spear of pain, in my right cheek that time. It really hurt. I screamed and cried and begged him to stop. I promised I would go into a convent. I said I would wear a chador all the time. But I didn't say the safe word. Hmmmm. Did I mention that I came so hard that I almost passed out from the pleasure? All over Daddy's pants. Then I got another big woodie! What an experience!
After about 20 swats, Daddy stopped.
I was sniffling and sobbing. And my cock was standing straight out. I had no idea that I would react with ecstasy to a spanking. Forget that safe word. I had continents to explore.
Gianfranco, I mean Daddy, was telling me he loved me and that it hurt him more than it hurt me to spank me. Goo was drooling from my fatally excited prick as he produced a soothing cream
"I'm going to rub this on you so you'll feel better, Tiffany. Now turn around."
I did and Daddy began to rub the lovely cream all over my red, abused bottom. It felt wonderful. And even better when he rubbed the cream in the folds between my bottom cheeks. Then he put LOTS of cream all over my anus and even in my anus.
No one had ever touched me there and all I could do was again begin to helplessly ejaculate my girlish cream.
I was having a really good morning.
Daddy didn't seem to notice my third screaming orgasm of the past hour. He just kept making me nice and open and slippery back there with first one, then two, then three fingers.
Was he going to fuck me?
This first activity wasn't going the way I thought. It was a LOT better, so far.
When I was loose and gooey and had regained most of an erection, Daddy sat me on his lap and asked, "Does that feel better, Tiffany?"
"Yes, Daddy," I said. "I know you love me." I kissed him.
Forget that Angelo kid. Gianfranco was a man and he kissed like one. He took my breath away. Moments later, and I still don't remember how it happened, I was on my back on the dining room table. What would Mom say? Daddy had my stockinged calves on his shoulders. Where were my panties?
Daddy's pants were down to his ankles. He held his big, pink cockhead at my anus. He smiled at me.
I prayed that the door wasn't going to be flung open by "Mommy" or Sister Perpetua from third grade, or the 82nd Airborne Division. Well, maybe the 82nd.
It wasn't. Daddy pushed. Ohhhhhhhhhhh. It was heavenly!!!! Daddy had prepared me so well that it just slid in. I was being fucked! My ass was full of cock. Twelve years of imagining it and it was finally happening. And it was incredible.
Daddy was firm, but gentle and loving. He kissed me a lot. I dug my nails into his back and gasped and moaned, whimpered and panted. I lurched and jerked. Daddy came first. I was desirable! I made a man cum in my bottom. And earlier, a boy in my mouth.
That fired my libido even more, making me wince and cum yet again. That time it was a couple of girlish drools, but it felt like a four-alarmer.
I was wondering if Gingerfredonia had a good emergency room when Daddy arose and kissed me sweetly. "Thank you, Miss Tiffany," Gianfranco said." I hope you enjoyed your first activity."
Oh, baby! And I had thirteen days to go.
Chapter Four -- No Roark, no Tattoo
Did you ever notice on the old Fantasy Island series, no one ever said, "I just want my cock sucked constantly for a week," or anything like that? I'm guessing that sexual fantasies would have been very big if there were really such a place.
Fulfillment thus far had been all I had ever hoped it would be. When I got back to my villa, I ate a large lunch of dry, lettuce sandwiches and water and napped for an hour. When I got up around two, I decided to spruce up a bit. I called Gianfranco and set it up to have my hair and nails done.
I almost asked if he would join me for some slap and tickle, but I wanted to pace myself. My balls felt pretty empty and I didn't want to disappoint anyone who would be seeking my gooies.
I had a lovely, relaxing afternoon and, when Gianfranco met me after my makeover, I could see he was impressed. Or able to summon a big erection on demand.
It was around six and I asked that Gianfranco take me to dinner. Apparently, he couldn't say no to me, which was a good thing. I hoped that men outside the spa would be equally powerless when confronted with my beauty.
I wiggled into a lovely little black dress, black stockings and five-inch-stiletto sandals and Gianfranco looked as if he wanted to fuck me right there.
So did lots of other men at the off-spa restaurant he took me to. That was really my first time in the real world and it was a large boost to my growing ego. Men were staring. Lusty stares. What would they think, I wondered, if they saw what was in my pretty panties?
Maybe they would like it.
We had a lovely dinner and I told Gianfranco all about my life. He seemed to know a lot already, which surprised and puzzled me. How did he do that? He told me that he had been at the spa since it opened and enjoyed the work very much. The ladies were charming, but none so charming as I? Was he trying to get into my panties? He was welcome to do so.
When we arrived back at my villa, I asked for his advice about next steps. He recommended two things. He said I needed more experience exploring a man's cock, which he was happy to give me. And he recommended catalog number 32-X for tomorrow's activities -- another high school scenario that would help me work out some issues.
I took him up on both suggestions.
I think he liked me as much as he said he did. I knew I wasn't his first tgirl. But his cock was very hard and vertical when we undressed each other. I loved kissing him and he consumed me with his embraces. He lifted my lacy bra and kissed and licked and sucked my nipples until I screamed in erotic desperation and made a huge cummy mess in my black satin panties.
Then I got that hands and mouth-on experience with a cock that the helpful personal concierge had suggested.
It's a service economy we're in these days.
Chapter Five -- Catalog Number 32-X
I was so hungry for Gianfranco's cock, but I took some time to examine it properly. He was naked. I was in my nightie and stockings. We had all night.
I explored his beautiful cock with my fingers, then my lips. I kissed it all over, stopping several times to refresh my lipstick. A girl hates to look frumpy. I gave his balls a nice, slow tongue bath, which he seemed to like a lot.
Then I decided that I would give him a first-rate handjob, a neglected skill in our cocksucking era. Gianfranco was most appreciative when I rubbed his peehole with the pad of my right thumb. I kissed him sweetly as I was pumping him, then stopped kissing and focused on the handjob, so I could witness the fruits of my efforts.
He was wincing in erotic agony as I slid my soft, girlish hand over his drooling cockhead. But it was still a surprise when, without warning, ropes of cum began leaping from his red peehole. Flying through the air like fireworks. Celebrating Tiffany Day, the day of my liberation from self-imposed exile. There would be a great deal more cum flying for that celebration and others I would declare.
Gianfranco truly loved that handjob, and told me so by sucking my nipples and giving my balls sweet caresses until my goo flew.
I sucked poor Gianfranco's cock off and on all that night, producing and swallowing five delicious loads of gooey cum. He even sucked my little dolly, mostly in self-defense, I imagine, and it was divine. Needless to say, it was the first time my balls had been orally drained and I adored every microsecond of the experience.
The next morning he kissed me beautifully and bade farewell. Then it dawned on me that he hadn't fucked me. How did I forget that? Well, there were lots of other opportunities waiting.
Another nice young man named Antonio picked me up for my activity. Gianfranco must have been resting. Once again, I was dressed as the girl a boy would most like to sit next to in high school.
Antonio said I would meet a girl named Allison and I was to take her lead.
I asked, "Is Allison a genetic girl?"
Antonio smiled. "That would be telling."
Hmmmm. I hoped I wasn't going to be expected to do anything with a GG. Yuck, I thought. GGs had often been mean to me, calling me a sissy and worse, most of my life. I didn't know how I would feel about sex with another tgirl. I had never met one, so how did I know?
Antonio showed me a picture of Allison. She was beautiful! The kind that Grant always lusted after. Grant could be so annoying. He should have figured that genetic girls didn't want you unless you had a tattoo or a police record.
Maybe Allison had a big cock under her skirts. That would be interesting. But I hoped she wouldn't be so pretty that I would be jealous.
I was tingling with the possibilities as Antonio dropped me at the "school" building I had been to the previous day. Same classroom. Same teacher. Same kids, except that Angelo, my lover of yesterday, had been replaced by Allison, in the same chair even.
When class was over, Allison sought me out. "You are coming over my house today, aren't you Tiffany? Carla and Diane will be there.'
Three girls? Hmm. If they really were girls. I was expecting more surprises.
Allison was a real yacker, gossiping about a lot of people I didn't know. These spa people were great actors. When we got to "Allison's house," Carla and Diane were waiting for us on the porch. Zowie! They were cuter than Allison! And she was a 9.9.
Maybe Tiffany was "bi." I was beginning to hope so.
We filed in the house and Allison led us back to the family room, where we all set down our books. Surprises followed in rapid succession.
Carla and Diane removed their blouses, then locked lips in a very tonguey kiss. Good gravy! It was true. Boys always suspect that when girls get together it's for "lezzie" stuff. It was true! At least in Gingerfredonia.
The two "tens" had removed each other's bras, exposing huge, floppy titties with big, brown nipples. Carla reached under Diane's skirt and divested Diane of her panties. I got a clear view of a very hairy, very wet, nasty-looking pussy.
Oh my. I was hard as differential calculus. Over girls.
Observing the live show, I heard sobbing behind me. I had forgotten about Allison!
I looked at her and through her tears, she said, "Oh, Tiffany, you don't love me any more. All you want is Diane's pussy."
I was really getting into the scenario at that point and said, "Oh, no, Allison. I love you!"
"You do?"
I nodded.
She smiled bravely, then sat on the couch, removed her panties and gave me a Miramax Theater view of her pussy.
It was spectacular. Shaved bare, with delicious pink lips, dripping with female arousal. Oh my goodness. I wanted to fuck her. It was true. I was omnivorous.
"Will you kiss it?' Allison asked.
Wordlessly, I answered. I got on my knees and lifted the little beauty's skirts. She spread her stockinged legs for me as I kissed, licked and ate her glorious pussy. When her little clitty emerged, I sucked it until she came five times and begged me to stop.
The little doll then lay on the floor and asked me to fuck her.
Well, I certainly didn't expect that. Carla and Diane were eating each other's muffies quite happily on the other side of the room. Allison was spread and ready. I pulled my panties down and off, removed my skirt, and mounted Allison.
I had never... Allison knew and she was gentle and helpful.
She guided me to her golden gate. I pushed. She squealed. I squealed. And was so excited that I almost blew my gooies right there. It was exquisite. So that was what I was missing. No sense getting all goofed up over what was missed. I had lots to look forward to.
Allison helped me get into a rhythm and I turned out to be pretty good at delivering a fuck as well as getting one. Allison caressed my balls and made a lot of noises that suggested she was enjoying herself. She also came twice and I knew she wasn't faking it.
When I spurted my cream into her, I was confused but happy. I liked making love with both women and men. As Woody Allen once said, "Bisexuality doubles your chances for a Saturday night date."
We kissed for a good half hour, then Allison said that the scenario was over, but she would love to spend some time with me back at my villa.
Should I? Oh, yes.
We left a carnally locked Carla and Diane -- I don't think they noticed that we left -- and returned to my villa, where we put on our tiny nighties and fucked each other's brains out for that afternoon, evening and some of the night.
The next morning, I was ready to go again, but Allison suggested that we save some for later. "Let's take a boat cruise today. Gingerfredonia is very beautiful."
Well. OK. If that was what Allison wanted.
Allison and I got onto a very nice, 50-foot yacht that belonged to the island's absolute ruler, King Fred. It was very well-appointed and staffed by a well-dressed, well-mannered crew of Gingerfredonians.
As we left port, I had a lot to think about. I was sure I wanted to be Tiffany, not that loser Grant. But did I want to be a "male lesbian" as the tgirls call them or a sissy cocksucker for most of the nice, attractive guys who came my way? Until the previous day, I was sure that I wanted to be on my knees sucking cock, taking big loads on my face and in my bottom.
But sex with Allison was good too.
Then it occurred to me. Why not both?
I was about to discuss my feelings with Allison, when I noticed that she had shucked her clothes and was standing naked on the deck of our pleasure boat, with the wind in her hair.
Was that an invitation for me to get naked and have sex with her? But what about the crew? I didn't think I could just screw in front of everyone like that.
Once again, though, I was judging the situation by my life experience, forgetting that I was in tgirl fantasy spa in Gingerfredonia.
I wanted to ask Allison for some guidance, but as I opened my mouth to speak, Allison said, "Come on, Tiffany. Get your clothes off. The crew is ready."
Huh?
I turned around and standing behind me were two hunky, naked crew members, stroking their very nice cocks.
Allison was bi! And so was I, apparently.
Allison was more than bi that day. She was cock crazy.
The first officer approached Allison. She got on her knees and took his long, fat, lovely cock deeply into her mouth. The mouth that had kissed me and sucked my cock only hours before. But, when in Gingerfredonia, one must observe local customs. I beckoned the naked captain over, stripped to my tgirl buff, and got to my knees next to Allison. The Skipper's rampant meat was inches from my red lips. I kissed its drooling head and licked him to sexual distraction as Allison smiled at me as she drove the first officer wild.
The sailor boys had big ball bags, heavy with cum, and they emptied them all over our pretty faces in short order. My eyes were stuck together by cum, but I was very happy. When I opened them, fresh sailors had replaced the lads who had just frosted our faces. They were also randy "tars" or "gobs" and all those other crossword words and gave a giggling Allison and me another gooey blast. I looked at Allison and decided that if my face were as cummy as hers, I wanted a picture of myself as a souvenir.
The sailors brought in fresh troops and, though my jaw was getting sore, I adored bringing the third nautical fellow to a creamy cum. As if my mind had been read, my picture was taken.
Trust me. I was a mess. But a happy mess.
I assumed that since we had drained the balls of the crew of six, our fun was over. I was wrong.
Allison suggested that I get on all fours. I did so, then felt lubricated fingers in my bottom. Greasing it. Opening it for men's pleasure.
Before the day was out, Allison and I were each serial buttfucked by three big-cocked crewmembers.
As a cleaned-up Allison and I pulled into port after a three-hour cruise I thanked Allison and whoever ran the spa (and whoever my benefactor was) for answering my dilemma. I was a cock-crazy tgirl. GGs were fun in a pinch, but men were the first team.
Chapter Six -- Even More Fantasies Realized
Allison drove me from the port, but instead of going to my villa, she took me to the house where I had been on the day "Daddy" had first fucked me. Were more hijinks in store?
Apparently so.
I kissed Allison goodbye and thanked her sweetly, since I didn't know if I would see her again. Then I walked toward "my" front door, not knowing what to expect.
The door opened and there was a very angry Gianfranco, playing the part of "Daddy" once again.
Why was he angry?
Then I noticed that he was holding a large, computer-printed, color picture in his hand. I was afraid I knew the subject matter.
Although I knew I was at a fantasy spa and that Gianfranco wasn't my Daddy, I was scared. What would he do to me? I thought, as a delicious shiver of fear and arousal tingled in me.
"Get in this house, young lady," Gianfranco said in a low growl. Ooooohhh. I was really trembling as I passed him and he gave my recently serial-fucked bottom a hard swat. Was he going to spank me again? Double-Ooooohhh. Despite all the laws of physiology, my panties were once again stuffed with my hard cock.
"Daddy" said, "My friend who works on the King's yacht emailed me this disgusting picture of my daughter with men's cum all over her face. Lots of men. And lots of cum. And you're smiling and happy, you little tramp."
Daddy wasn't happy. I began to shake. What would he do?
"A spanking will be too easy for you, Missy. You want to be a tramp? I'll show you how to be a tramp."
What would he do? I found out.
Daddy grabbed me by the wrist and pulled me through the house to the master bedroom. He opened the sliding glass door that led to a terrace with a cast-iron railing.
"Get out there, Tiffany. Turn your back to the house, drop your panties to your ankles, grab the railing and bend over."
I surveyed the situation. The house was not on spa property and the terrace overlooked a busy street. People were walking by and some had already started to look in our direction. Did he want me to expose myself publicly and then fuck me?
My cock was throbbing like a struck gong.
Still, I began to cry and protest. Which drew a larger crowd. It was humiliating and degrading. And very exciting. My safe word was nowhere to be heard.
I whimpered and complained, but I followed "Daddy's" orders to pull my panties down to my high-heeled ankles. Then I grabbed the railing and quivered from shame as my stiff cock pointed at the giggling, growing crowd.
I had no idea that humiliation could be so exciting. Fulfillment was helping me explore things that a few days ago I had difficulty imagining.
There were about 30 people looking at me and snickering at my predicament as "Daddy" lectured me.
"You want to be a little tramp? Fine. Let's let everyone see what you're like."
Then he parted my bottom cheeks, rubbed his big, hot, hard cock against my anus, which was still sore, but gooey from the serial fucking I had been getting earlier that day.
By all rights, I should have not had an erection because of a) shame and b) being fucked out. But no one told my girlie stick. She was thick, stiff, dripping and throbbing.
And when Daddy fucked me in front of all those people, I drew cum from between my toes or somewhere, and threw a huge load into the stratosphere.
I screamed from joy, humiliation, lust, and to give Daddy encouragement so he would keep doing that.
When I came hard, the crowd oohed and aahed and began to applaud. I barely heard them, since I was enjoying the fucking very much.
And to think that I had considered that maybe I liked women better.
When Daddy orgasmed, he held my hips and pumped me to overflowing with manly goo. Then he turned me around, held me and kissed me as his goo ran out of my bottom and down my thighs, much to the delight of the crowd.
Daddy and I bowed to their applause, turned around and went into the house, closing the door.
Daddy was Gianfranco again.
"Did you enjoy your day, Miss Tiffany?" he asked.
In answer, I smiled, fell to my knees, and gave Gianfranco a ball bath and cock sucking that most men only dream of.
Chapter Seven -- And now for the main course
I slept alone that night. Thank goodness. I was exhausted.
But I was very happy. And very excited about what was going to happen next.
The staff of Fulfillment had amazed and delighted me at every turn, so I was expecting the excitement to continue when I awoke the next morning. I was not disappointed.
I stretched and yawned as I recalled the events of the previous day. I had produced a bucket of cum, both from myself and my numerous partners. I was such a little slut.
I removed my nightie and admired myself in the full-length mirror. As soon as I returned to the real world, I vowed, I was going on hormones, was getting my Adam's apple scraped and was getting some breasts. I knew I was going full time as Tiffany. It would shock and disgust some of Grant's acquaintances, but I had to be Tiffany. I just had to be.
I bathed and primped, then dressed in a red summer dress with white polka dots, tan stockings and white, five-inch, stiletto sandals.
Not bad, I thought as I considered Tiffany in the mirror.
Then I called Gianfranco for his activity suggestions.
"I'll be right over, Miss Tiffany," my hunky, spunky concierge said. "And I'll bring my suggestion along."
That was interesting.
Five minutes later, there was a knock on my villa door. I sissied over to it in my skyscraper heels, opened it and saw Gianfranco. And Bill Emory, my best friend from high school, who I had stroked myself raw dreaming about, but never had the guts to confide in.
I did exactly what you would have done. I screamed and slammed the door shut.
My chest was heaving and my mind was racing as I threw my back against the door to keep Bill away. Far away.
I could never face him as Tiffany. Everything about it terrified...the old me. Wait a minute. I wasn't the old me anymore. I was new and improved. I was Tiffany, not Grant. Then I panicked. Had I chased him away? Desperately, I flung the door open, praying I could catch up to them in my five-inch, fuck-me-hard-and-put-me-away-wet sandals.
But Bill and Gianfranco they were still standing in exactly the same spots, with broad, self-confident smiles on their handsome faces. Men can be vexing.
I brushed my hair back with my right hand, then said, "Hello, Gianfranco. So nice to see you again, Bill. Won't you both come in?"
They did. I mean, at least Gianfranco did. Bill held me in his arms and gave me a big, tonguey kiss.
It was a white-hot kiss and I was seconds away from creaming my panties when he broke it off.
"I've been wanting to do that since the day we met ten years ago," the wonderful dreamboat said. "I guess neither of us had the guts. Thank goodness Gianfranco contacted me, told me everything and invited me here."
I looked at Gianfranco, who was looking like one of those angels who just did a good deed for a mortal. What a sweetheart he was! But how could he have known about Bill? Or that Bill would want me?
Who cared? Bill kissed me again and when he stopped, Gianfranco was gone.
Was Bill going to make love to me right then?
No. Rats. He was too much of a gentleman. But since we had waited ten years, I guessed we could wait a few more hours. At least until they freshened the room.
Ten years we wasted. Afraid to tell each other the wonderful truth. Content with a sad lie.
But that was the past.
Bill had a car and he took me to a lovely spot overlooking the ocean. We talked and kissed and talked some more. He praised my beauty and sweetness . And he begged for my forgiveness for not connecting with me earlier.
There was my answer. Bill had figured everything out and he was my benefactor for the spa. What a relief to know that.
I hugged Bill and thanked him for paying for my spa visit. But from the expression on his face, I knew I was wrong.
"I was called by Gianfranco two days ago, Honey. I suspected and hoped you were a tgirl, but wasn't sure until Gianfranco's call. And I didn't arrange anything. It looks to me as if your benefactor arranged for me too."
What a mystery.
Oh, well. I would worry about it after I got a few big, hot loads of Bill's cum in my bottom and throat.
First things first.
Messing around with all those spa-arranged situations was LOTS of fun, but when Bill got me back to my villa and put the pork to me, I knew I had found true love.
Bill fucked me hard and made me squeal with joy. He was gentle, but not too gentle. Firm, but not too firm. And his cum was delicious.
He stayed with me at the spa and no one saw us for the last ten days of my wonderful, life-altering experience. On the last night, Bill asked me to marry him.
I cried and sobbed. Sucked his cock. Said yes. Got on my back and welcomed his big cock to paradise. Then, like the woman I was becoming, set out to plan the wedding.
The next day, Bill and I were sad to leave the spa, but delirious about the prospect of our life together. We knew it would be difficult at times and that not everyone would be pleased about us. But we hoped, at least, that our parents would be happy for us.
Not much chance of that, though, we agreed.
We said a nice farewell to Gianfranco -- not the kind of farewell he would have wanted from me, I would hope -- but I was an engaged woman!
But Gianfranco wasn't through with me quite yet.
"Miss Tiffany," he said. "Someone else wants to see you before you go. The person who paid for all this and set it up."
My benefactor! Oh!! I was trembling I looked at Bill, but he was as puzzled as I was.
Who was it? And why?
Then all was revealed. And it all made sense.
Gianfranco opened a door and out stepped -- Daddy! And Mom! And Bill's mother and father!
They knew. They approved. They manipulated the whole thing, even to the point of letting me get all the nastiness out of my system first.
I cried buckets as the room filled with future in-laws. We hugged. We kissed.
And looked forward to very happy lives.
Please tell me what you think at gingerfred2005@yahoo.com.
My other stories on nifty:
"Acting Up" transgender -- control "Panty Pleasures" transgender -- young friends "Woodville" transgender -- tv "Mothered" transgender -- control "Panty Town" transgender -- teen "Tradition" transgender -- teen "Punished" transgender -- high school "Panty Paradise" transgender -- teen "Kevin and Molly Go to Camp" -- transgender -- teen "Lovelife" -- transgender -- high school "My Three Sissies" -- transgender -- tv "Acting Out" -- transgender -- high school "Explorers" -- transgender -- high school "Pantied" -- transgender -- young friends "Rebuilding" -- transgender -- teen "The Au Pair" -- transgender -- surgery "Birthday Girl" -- transgender -- teen "Genes" -- transgender -- high school "Brothers in Panties" -- transgender -- teen "Coach" -- transgender -- control "Intervention" -- transgender -- high school "Winners" -- transgender -- teen "Teased" transgender -- high school "Irish Girls" transgender -- teen "Finished" -- transgender -- teen "Role Model" -- transgender -- high school "Freedom" -- transgender -- high school "Panty Fiesta" -- transgender -- control "Experiments" -- transgender college "One Fine Day" -- transgender -- teen "Stiff Resistance" -- transgender -- teen "Poker" -- transgender -- tv "Panty Sabbatical" -- transgender -- high school "Published" -- transgender -- tv "Stripped" -- transgender -- high school "Trained" -- transgender -- control "Something Better" -- transgender -- tv