Fantasy Weeend

MF, MM, MMF, FMF, Fetishes: sexual role-playing, cross-dressing, domination and submission, and pain.

The youngest person in this story is a 19 year old receptionist.

4Play has given me permission to make modifications and additions to his story "Date Night."

I changed the title to "Fantasy Weekend." I also added the first paragraph to chapter 1, deleted chapter 5, and made a few other minor changes to the original story. Chapters 7 through 10 are added chapters.

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Fantasy Weekend—Chapter 1

Originally written by 4Play. 4Play gave me permission to modify his story.

My name is Donald Smyth, age 28. I have an MBA from Princeton and would be considered a geek at 5"10" and 145 lbs. My wife, Chris, is also my age. She is very pretty, 5'5" 122 lbs and has a degree from Wesleyan. We have been married five years and she still works because she enjoys her work. I have an income of $120,000 per annum and I love Chris very much. So, as far as I am concerned, her working is not necessary.

Tonight was the start of what I hoped would be the new and improved "Fantasy Weekend" and I'd spent the day in a high state of anticipation. Chris and I had created the "Fantasy Weekends" several years ago to merge our divergent sexual desires into a mutually satisfying relationship.

My sexual tastes ran to the more exotic side of the spectrum bondage, forced oral sex, prolonged sessions, feminization and role reversal were exciting fantasies for me. Chris playing the dominant role was a common theme in all of these schemes.

Chris, on the other hand, much preferred warm, tender romantic loving. Kissing, caressing and cuddling were turn-ons for her. She claimed to have no fantasies of her own and therefore found it difficult to act out mine. While admitting that she could probably play the dominant role with someone else, she was reluctant to do it with me. She was afraid that playing games with me in the submissive role would turn me into a wimp. Yet, she loved me and wanted to please me.

Our compromise solution was our planned Fantasy Weekend scheduled every other weekend. On these weekends we would engage in some of the wilder sexual practices, while the rest of the time would remain normal. With my special desires mostly satisfied on a scheduled basis, I was content. Chris found that she was able to play "games" occasionally as the rest of our live together was exceptional. Needless to say, I look forward to these Fantasy Weekends. Chris found herself enjoying most of these nights despite a certain reluctance to let go. She still felt uncomfortable in the dominant role since she had never been an aggressive person, but she tried to keep me happy. When I was happy, our lives went smoothly. This plan had worked, but not well as I wished. I was always encouraging her to become more dominate; however Chris would always hold back and, in spite of my assurances, she was afraid that she might go further than I wished.

Then one day Chris told me that she was going to give it her best effort; however, for the next three months I would have to agree to do whatever she decided and allow her total control. Then she said, "After the three months we would talk about it and discuss if we needed to make changes." Not knowing what I was getting myself into, I readily agreed.

Tonight things would not be routine. I sensed a new, more determined attitude the moment Chris walked in the door from work. Without our usual casual conversation about the happenings of the day, she ordered me to go into the bedroom and take off my clothes. As I left to comply, she poured herself a glass of wine. She mentally reviewed her plan and became resolutely determined to carry it out.

When she walked in the bedroom and saw me standing naked, a smile came to her face. "Very good", she praised. "You mind well." She had me put leather cuffs on each wrist as she passed the strap around the vertical posts of the poster bed. After snapping one wrist to one end of the strap, she stretched my arms so she could secure the other cuff to the other end. I now stood naked in helpless bondage and totally at her mercy. Her sweet smile disappeared as she informed me "I had to tie you up since I have a plan and there are parts of it you won't like! Now, it doesn't matter whether you like it or not! I am in total control!" She was so right! Straining against the bonds was futile. They were unbreakable. It suddenly dawned on me that this was a game that would not be over in an hour or so.

Chris went into the small bathroom and returned with my shaving mug, brush and razor. As she worked up the lather in the cup, she said "You've been hinting that you wanted me to turn you into a woman for some time, well tonight's the night!" Shaking her head sadly, she said "I am going to transform you into my slave girl and you will get the full treatment! Poor dear, I am afraid you have no idea what you are getting into, but it is too late to back out now! You wanted this and you're going to go through with it all the way!"

Using the brush, she soaped each of my armpits, and then took the razor to shave them clean. "Mmmm nice and smooth," she remarked running her hands over the newly bald areas. "This is how a lady keeps her arms," she informed me. Next she knelt in front of me and soaped up one leg, then carefully shaved it from my toes to my crotch. This process was repeated with the other leg before moving to my genitals. After applying a generous coat of lather, she carefully shaved my scrotum warning; "Hold very still, or you'll become a real woman!" I didn't move a muscle until she was finished.

The hairs between my legs and around my ass received the same close shave treatment. My pubic region was shaved to form a small triangle before she stood up to lather my face. When I realized that she intended to shave off my beard and moustache, I finally protested. It had taken a long time to grow that foliage, and I didn't want to lose it. As my mouth opened, Chris shoved the soapy shaving brush into it demanding, "Keep your mouth shut bitch! YOU wanted this game, NOW you are going to get it!"

She shaved my face and neck, completely removing all traces of hair while I stood in meek silence. Playing the dominant role she was determined to show me that my wishes were inconsequential.

The shaving gear was put away before Chris rubbed my body with a sweet smelling lotion. "A lady has to keep her skin nice and soft," she cooed sweetly as she rubbed it in. When finished with the lotion, she brought out the bright red nail polish and painted my toenails. "Very pretty dearie," she exclaimed admiring her handiwork. As my fingernails were being painted she remarked casually, "Some of those long fake fingernails would look wonderful on you, we'll have to get some when I take you shopping with me." My eyes widened in surprise, she was serious about this!

A roll of duct tape was brought out and strips of it were used to form my chest meat into female breasts. "I thought about buying you a set of falsies, but decided that this would be better. Now I can get at your nipples to control your movements, and so on." She explained. Once satisfied that my "titties" were to her liking and held firmly in place, she moved down to my crotch. My cock was pulled between my legs and secured there with more duct tape so that while being able to walk, it would remain immobile. "We won't be using that for sex." She announced, and then she continued, "As my woman you'll just have to sit down to pee as any girl must. Now the experience will be much more realistic, since it's the only way you'll be able to go." She chuckled at her diabolical way of turning even routine urination into a part of my training as her submissive. I was to find it necessary to wash my bottom after each time I urinated. Only one of many new difficulties I was to encounter.

A pair of pantyhose were put on my feet, and then slowly pulled up my hairless legs to my waist. High-heeled shoes were placed on my feet making it difficult to maintain my balance as I awaited her next whimsical idea.

Chris stood squarely in front of me, and pinching one of my nipples in each hand, kissed me forcefully. My cock throbbed trying to become erect, but unable due to its confinement. "Don't go away." She said with a grin as she left the room. Ha! Some joke. I was still secured by my arms and standing in high heels. Looking down at my body was a disconcerting experience. My breasts were small, but real and my legs encased in panty hose with no protruding cock, looked very feminine indeed. Especially so with the painted toenails and high heeled shoes. A dramatic change in such a short time!

Chris walked back carrying her make-up case, her refilled wine glass, and a mirror. The mirror was propped up on the dresser so I could see my helpless state for a few minutes while Chris sipped her wine. When SHE was ready, she warned me, "Watch very carefully as I demonstrate how to apply makeup. I'll show you this time, but from now on whenever I want you as my slave girl, you'll do it yourself." As she rubbed a base coat on my face, I watched in stunned silence realizing that she'd already planned on making this a regular occurrence.

Chris smiled to herself saying, "You know it's going to be fun to call you from work, tell you to get ready and KNOW that you'll do all of this preparation before I get home. YOU can meet ME at the door in a negligee with a drink." She laughed, "As you get trained in your slave girl duties, my life is going to get a LOT easier. After all, that's the whole idea of having a slave in the first place."

Applying blue eyeshade on my eyelids she noted, "This will make you look like the trampy slut you are." Long fake eyelashes were added and a heavy coat of mascara applied, followed with the eyeliner. My eyebrows were darkened and lengthened. She softly muttered to herself, "Maybe I should shave these off too, so the bitch would have to draw them on every morning." Fortunately she didn't carry through with that notion. Rouge was put on my cheeks and bright red lipstick on my lips as I stood helplessly watching this transformation proceed.

Chris placed her blonde wig on my head saying, "This old wig doesn't do you justice; we'll need to get you a new one." Obviously she planned for this game to continue into the future, as spending money on sex toys wasn't something she usually even considered. After fastening a pair of her old clamp on earrings on my earlobes, she stepped back to admire her creation. "You make a fine looking woman," she praised, and then added, "Now you need to learn to act like one."

She strapped on a dildo stating, "I am going to play the male role whenever I wear this. You will be my slave girl, and as such you WILL perform all of my normal tasks and still be constantly available for MY sexual pleasure." The cuffs were removed from my wrists as she said, "We won't need these restraints now that you know your place. In your condition you'll make a better woman than a man anyway." Looking at myself in the mirror, I had to agree with that assessment.

"It's too bad, but I'm afraid you won't be doing any swinging for quite a while," she said with mock pity, adding, "None of our friends would swing with something that looks like you, would they?" I answered meekly, "No Mistress." Upon hearing this she gave me slap on the rear demanding, "When I am wearing this, YOU WILL call me SIR!" I was shocked by her forcefulness, but managed to reply, "Yes sir."

She had me put on a lacy, black nightie that barely covered my buns. In the mirror I could see that with the tape now concealed and only the cute little bulges of my breasts showing, the image was complete! I did look like a woman! Chris had put on a pair of men's shorts with the dildo protruding from the fly, and one of my long-sleeved shirts. In appearance, we had already reversed roles.

Chris kissed me firmly, and then forced me to kneel in front of her. She pressed the dildo to my lips ordering, "Kiss my cock slut." She added, "All of us men love oral sex." I lightly kissed the head of the dildo feeling very humiliated by the homosexual implications of this action. "Take it in your mouth slut." She commanded. My lipstick covered lips parted and she quickly thrust the dildo into my mouth. I gagged at the intrusion and Chris with feigned concern said, "She doesn't like sucking cock?" Then she ordered, "Suck it good slut." She asked, "You do want to be a good slave, don't you?" Now really into her dominant role, her hips kept thrusting that dildo in and out of my mouth so I was unable to answer.

"Don't displease me slave or I'll tie you up and whip your ass bloody." I knew that she was serious about playing this dominant role and determined that I behave in the manner befitting the slave girl role she'd assigned me. "By God," she declared, "If you want to play kinky games, we'll see how you like being totally submissive!" She kept me at my chore until the sensations of the dildo on her body combined with the feeling of power brought her to orgasm. Her thrusting slowed and at last, she withdrew that horrible instrument from my mouth. "Not too bad slut, you make a pretty good cocksucker." She continued by saying, "With enough practice, you'll be a great cocksucker!"

Chris walked behind me handing me a jar of Vaseline and said, "Pull down your pantyhose and you'd better smear this on your pussy to save yourself a lot of pain. I'm going to fuck that virgin pussy and you're so nervous that it'll probably not get wet." I pulled my pantyhose down to my ankles and liberally smeared my ass, both inside and out. "That's a good girl, get yourself ready for your big stud." she cooed.

Kneeling behind me, forcing my legs apart she used pressure on my back until my face was on the floor. I was wide open and ready for HER pleasure. Pressing the head of the dildo to my asshole she cautioned, "This may hurt at first, but you'll get used to it, and in time get to love it." As the head was forced inside me, I moaned, "It's too big SIR!" Chris just chuckled, "It's just your bad luck that your master is so well hung. Don't worry, bitch, you will learn to take it all inside. I am going to give you plenty of practice!"

The dildo was slowly forced in until I could feel the attached balls against my body, then eased back out part way and these strokes repeated at an ever increasing pace. Her hands reached under my nightie and pinched my nipples. Thus impaled on her cock, the hands on my teats were controlling my movements, causing my rear to rise to receive each thrust. With ever increasing vigor, she was fucking me. The portion of the dildo inside of her was stimulating her nearly as much as the pressure on her clit. Her passion rose in direct proportion to her speed and the force applied. I was helplessly being raped and my moans of pain only served to enhance her feeling of power.

Finally, she achieved organism and slumped across my back, kissed me on the neck and pulled out of me. I was weak from the assault. Chris got up and I lay there for a few minutes. My mouth ached, my nipples ached and my poor ass throbbed from its violation. At last I got up and hobbled to the bathroom where I sat on the toilet and urinated. Due to the position of my taped up cock, some urine sprayed on my ass cheeks. After carefully wiping the remains of the urine and the slime oozing from my asshole, I took a washcloth to wash carefully my private parts. I pulled up my pantyhose, arranged my wig that had moved during the vigorous rape, straightened the negligee and went back to the bedroom. The high-heeled shoes made walking difficult which Chris noted by saying, "You walk like a clod." She suggested, "When you walk in heels, take small steps. Put one foot in front of the other. It'll give your ass a cute little wiggle." She had me walk up and down the hall several times until she was satisfied, then ordered "Remember to walk like that all the while you are the slave girl even while doing domestic chores." Chris walked to the family room to work her crossword puzzle and told me to fix her supper. "I'm in the mood for a T.V. dinner; you'd better just have a salad. You have to watch that figure, babe."

I fixed her a T.V. dinner and made myself a salad. We ate supper quietly before I cleared the table. Chris had me empty the dishwasher and set up the coffee for morning. She said, "Turning into my slave girl took some of my precious time, but as you learn your duties, it may turn out to be worth it. It's nice to sit here watching YOU work while I relax."

"Take one of our movies and put it in the Blu-ray player, make it a love story," she ordered. I thought for a moment and put the movie 'Love Story' in the machine. She motioned for me to sit beside her on the couch. During the movie, Chris necked with me. She kissed and caressed my body, played with my breasts and even slid her hand inside my pantyhose to play with my pussy. By the end of the movie, she said, "You really have got me turned on now, let's make love." She had me lay on my back in front of the fireplace, placed a big pillow under my behind and got on top of me. She slid my nightie up, pulled off my shoes and pantyhose. Spreading my legs she forced the dildo inside of me and once again fucked my still aching ass. "You love this, you little slut, don't you?" She asked. When my answer wasn't immediately forthcoming she slapped my ass and repeated, "Don't you?"

I gasped out, "Yes Sir!"

"Then tell me how much you love it slut, a man's ego feeds on praise," she ordered.

"Oh sir, it feels so good." I lied, since it felt like that dildo was tearing my insides wide open. "Your big cock fills my pussy so full, I love it."

She smiled and without missing a stroke said. "You'd better work on that voice. You need to speak in a higher tone, one more suitable to your current status. When I take you to public places, I want people to think you're my girlfriend and not some wimp in drag." The thought of being in public dressed as a woman was so utterly humiliating. Nevertheless, it was so exciting that it triggered my orgasm and I came all over my stomach. Chris's sneer clearly showed her disgust, but she continued ravaging my poor ass until she again reached her climax. "Look at this disgusting mess you made on MY property!" she exclaimed. Using her hand she scooped my cum from my stomach and forced it into my mouth saying, "That's a good slave, swallow every bit of that slime." She had me lick her hand clean before sending me to the bathroom to clean myself.

Upon emerging from the bathroom, Chris took me by the hand and put me to bed. She crawled in beside me, caressed my body lightly, kissed me and cautioned me, "You'd better get some sleep dearie, you've got a busy day tomorrow." Then she rolled over and went to sleep. It was a long time before I could get to sleep. SHE'D had several orgasms during the course of the evening, while the only one I had was even turned into a source of my humiliation. In my fantasies serving Chris, as my dominant Mistress had been a big turn on, but the actual experience had been only pain and humiliation. I already regretted getting into this, but had promised in my eagerness to go along with ANYTHING SHE WANTED, and now was stuck with living up to my word. Finally I drifted off to sleep.

SATURDAY, I was awakened by Chris playing with my titties. From a deep sleep to my function as a sexual servant was a swift transition! As she rolled over and moved behind me, I saw myself in the mirror and was instantly reminded of my slave girl role. The head of the dildo was again forced inside my ass with difficulty and Chris snarled, "You are such a tight little bitch. If your pussy grows shut this fast, I'm going to have to think of some way to keep it opened up!" She fucked me vigorously until achieving her orgasm, all the while making me moan with feigned pleasure. Though less painful than the first experience, it was nonetheless humiliating to be so used. With a light slap on my fanny, she told me to clean myself up there was WORK to be done. Meekly I complied, already dreading this day.