The Right Decision

What's the right thing to do?

If only I had moved back with my parents when the semester ended I wouldn’t have ended up in this situation.  But I wanted to be independent.  I wanted to get a job that would let me stay near campus a half a continent away from them.  The job sounded awful… live in housekeeper for a rich couple.  But it not only paid well, it provided me with free room and board.  Keeping up the Winslow estate certainly wasn’t easy as I had to do it all.  Manage the acres of lawn and gardens.  Clean up the entire home.  Do all the laundry.  Prepare all of their meals.  The only time I had to video chat with my girlfriend Britney was late evenings.  She ended up moving back with her parents and was so jealous of my freedom.

She loved teasing me about the job, and even started up a game.  Each day she’d assign me a role and I had to play it out and send her a picture.  Dressing up as the ‘pool boy’ was easy.  Playing as the ‘butler’ required me to raid Mr. Winslow’s closet for one of his black suits.  Finding the coveralls in the garage made a good costume for the disgruntled Gardner.  When I told her about the sexy French maid’s costume in Mrs. Winslow’s closet she told me that I’d have to be that the next day.  It seemed ok as both of the Winslows were traveling and I’d have the whole estate to myself. 

When Mrs. Winslow came home early and caught me dusting in the costume she was surprisingly calm.  Instead of having me change and throwing me out she sat me down and told me that she always suspected I liked to cross dress.  I had no time to think about the consequences and agreed with her assessment.  Better to be thought of as a cross dresser than getting fired for rifling through their closets and wearing their clothes.  While she was smiling there was a firm edge to her voice as she told me that she was going to help me explore that side of myself.  There were a few conditions though.   One, I’d have to do everything she said without question or hesitation, otherwise she’d throw me out.  Two, I couldn’t let her husband know as he wouldn’t support this fetish of hers.  I was trapped in a corner… agree to let this rich powerful sexy woman dress me up all summer, or get thrown out.   To this day I’m not sure if I made the right decision. 

Mrs. Winslow started spending more time at home.  Whenever Mr. Winslow left she worked with me.  The first few days it was simply wearing a feminine version of my regular clothes.  Tight fitting jeans, girly sandals, and pink tee-shirts.  But every day she’d throw more and more at me.  She taught me how to put on makeup.  She had me shave my body smooth.  The jeans were replaced with skirts.  The sandals with heels.  She bought me matching lingerie sets and taught me how to put on stockings and fill out my bra cups.  She had me take online lessons on how to speak with a feminine lilt.  She had my ears pierced and added jewelry to my daily routine.  When my hair grew out long enough she brought her stylist home and not only cut my hair in a way that could be styled as either feminine or a slightly ambiguous male style.  She even had it colored.  

The lessons on sex were fun, but difficult.  She started one afternoon showing me how to kiss like a girl.  I was encouraged to caress her but I had to keep my touch light and caressing.  The next day she showed me how to worship her breasts using just my lipstick painted mouth.  Feeling her own tongue flick across my nipples was a good teacher.  She never wanted to see the masculinity hidden away under my panties so I learned how to tuck myself away.  By the end of the week I found myself lying back on their bed as she lowered her sex down to my waiting tongue.  While we had plenty of sex, Mrs. Winslow focused on me dressing and acting like a regular girl.  After a month of this though, it was getting harder and harder to hide this from Mr. Winslow.

Mrs. Winslow was out shopping with her society friends when he returned from this business trip a day early.  I didn’t even know he was home until I felt his hand slip up my skirt and cup my panty covered ass while I was bent over vacuuming their bedroom.  My startled scream sounded so damned effeminate.  When I turned around he was surprisingly calm.  Fearing what he would say I started to explain but his beefy finger over my painted lips silenced me.  He said that he had always suspected that I liked to cross dress.  While he was grinning there was a firm edge to his voice as he told me that he was going to help me explore that side of myself.  There were a few conditions though.  One, I’d have to do everything he said without question or hesitation, otherwise he’d throw me out.  Two, I couldn’t let his wife know as she wouldn’t support this fetish of his.   I thought I was trapped before… now I was truly between a rock and a hard place.  To this day I’m not sure if I made the right decision. 

For the next month the only time I was ever dressed as my normal self was while both of the Winslows were home.  A normal morning would start with me dressed in my boy clothes as I prepared their breakfast.  Once Mr. Winslow left for work Mrs. Winslow would have me change into my girly clothes.  After a few hours of either working or taking femininity lessons, Mrs. Winslow would leave for her afternoon out.  Mr. Winslow would inevitably show up minutes later.  He appreciated that I was doing so well dressing as a girl, so he started to teach me how to be sexier.  Sluttier.  Replaced my sensible heels with stilettos.  He changed my nude stockings to fishnets or silky smooth black.  My down to earth skirt and blouse were replaced with a mini skirt and tight low cut slipover.  He even had a pair of breast forms so that I’d fill out a C cup bra.  He taught me how to be a wiggling giggling slutty girl.   As soon as we heard Mrs. Winslow’s Mercedes pull into the driveway he’d rush me upstairs and have me change back into the boy clothes. 

When Mrs. Winslow went on a weekend getaway with her friends, Mr. Winslow started my lessons on sex.  I spent Friday afternoon leaning how to kiss.  I was encouraged to caress him but I had to keep my touch hurried and needy.  Saturday he showed me how to worship his nude body.  I had to touch every part of him using just my lipstick painted mouth.  Having his hand guide my head forcibly around was a good teacher.  By Sunday afternoon I found myself lying back on their bed as he fed his thick cock into my waiting mouth. 

The first blowjob was hard but thankfully quick.  As Mr. Winslow guided his spilled cum from my chin back into my mouth using his finger he promised he would last longer the next time.   While I cleaned up and reapplied my makeup he pulled out a girly magazine flipped through it.  By the time I was presentable he was as hard as a rock again.   He did indeed last a lot longer on the second blowjob.  He taught me not only how to use my tongue but also how to deep throat him.   There was no cum to clean up that time as he shot directly down my throat.  Instead of moving off of me, Mr. Winslow reached behind him and started roughly fingering my own small cock.  The lesson continued as he taught me how to lick him clean and use my tongue to get him hard again.  All the while he kept me on edge without allowing me to orgasm myself.  Just as he returned to full staff and started feeding me his thick pole again I was shocked to hear Mrs. Winslow’s voice say “She looks so adorable like that darling!  Did you tell her yet?”

My eyes flew open and I tried to back away from Mr. Winslow’s invading member, but his hand quickly found the back of my head and started working my lips up and down his shaft.  Mrs. Winslow knelt on the bed next to us, kissed her husband with a passion I hadn’t seen them share before.  His hand never stopped teasing between my legs while her hand replaced his behind my head and encouraged me to continue as they explained what was going on.

Mr. Winslow told me that they shared a strong fetish for girly boys.  That they had been searching for someone ‘like me’ for years and years.  Each time they caught one of the boys in a compromising position they’d make a similar offer as I received.  Most left immediately.  A couple had stayed and enjoyed Mrs. Winslow’s lessons, but refused to stay once he had joined in the fun.  I was the only one to get to this point…. And they both wanted me to stay.

Mrs. Winslow explained that she hadn’t been on a weekend with her friends.  Instead she had flown out to meet my parents.  She said they were naturally surprised to learn about my desire to be girly and feminine, but when she showed them all the photos and secret videos they had taken of me that they tearfully agreed to let me stay with them.   That they in fact were no longer interested in having me ever come home or supporting me in any way. 

Mr. Winslow went on to say that I was free to make my own choices.  That if I didn’t want to live with them as their plaything that I was able to leave at any time.  But if I chose to stay they would help me in every way they could.  They had a doctor friend who would start me on a hormone regimen that would increase my femininity.  They had friends at the university who would change all my records from male to female and that I could continue my education.  He even said that if I wanted to continue to see Britney that I could, especially since she had been on this from the beginning.  

When they stopped speaking and were smiling down together at me Mr. Winslow’s hand started picking up speed on my groin while Mrs. Winslow’s hand left my head.  She said if I agreed that I should finish Mr. Winslow off all on my own.  To this day I’m sure I made the right decision.  

source:  fuskator