Not even one full semester and I was flunking out of college. I knew this was gonna happen. I was never good in school and barely maintained a "C" average. I hated sports too. No reason to think I would do well at college but my parents had insisted.
They had money and even though I could only get into a state school, they were proud.
Until they saw my grades that is.
Dad had told me that if I didn't graduate that I couldn't come home or work in his business doing landscaping and grounds management. Not that I had any interest in that anyway but not being allowed to come home was hurtful, even for my mom whom was quite a bit more sympathetic.
So I started calling around to relatives looking for a place to crash. All my cousins told me no and so did my uncle on my father's side but my aunt on my mother's side said I could rent a room in her house and even pick up some paid work sweeping floors in her shoppe.
I waited around college for a couple weeks to see if my grades would improve and I really did try but to no avail so I accepted Aunt Mary's invitation. At least I would have a place to live and a little bit of money coming in till I could find a decent job.
I took a Greyhound bus out to my aunt's place with the full weight of failure hanging on me.
"Hello Cammy." my aunt said giving me a great big hug. I hated that nickname. My aunt always added a "Y" to the end of everyone's name so Jo became Joey, Mike became Mikey and Cameron became Cammy. Ugh. Double ugh.
"Hi, Aunt Mary, thanks for letting me crash. Dads all in a twist about me flunking out of college and wont let me stay at home." I said as I tossed my bags in the trunk of her Cadillac.
"Your father is an asshole, always was. I warned your mother about him many times but she only saw his bank account. Now she's paying the price in a loveless marriage. Remember this Cammy dear, happiness is always better than money." my aunt said. She had an annoying habit of talking forever. "Oh and by the way. I haven't cleared out everything from your room yet, I hope you dont mind. I wasn't sure you were coming after all."
"Yeah, I stayed at school and I did try it's just not for me" I explained.
"Well like I said, happiness is far more important than money so if college wasn't making you happy then find another path. Maybe coming here is the start of a whole new life for you. By the way, I'm expanding my workshop and I have plenty of work for a few months the help you get on your feet." she said.
She kept talking about family, her dress shoppe, what was for dinner, what mom was like as a kid. It went on and on and on. She did like to talk.
We got back to her house, a grand place in town with more space than she would ever need and I was shown to what would become my room. Right now it was used for storage and was full of sewing mannequins. There were at least thirty of them standing all over and more than a few boxes piled up as well. There was a bed but it was piled high with dresses that looked as if they had been there for a few years.
"I'm so sorry about the mess. I'll tell you what. Since you're gonna be working for me, why don't you start by cleaning out this room for me. It'll probably be enough work to give you a full paycheck to start with. Plus the room will be the way you like it. Huh, what do you think?" she offered
Get paid to clean my own room? It was a huge room too and anyone would be glad to have it.
"Hell yeah. I can do that but where do I put all this stuff?" I said.
"Right then. You can put everything you don't need in the store room plus you'll be cleaning that out too. Like I said, I've got a ton of work for you. It'll be nice to have someone around to talk to. I can never keep anyone on staff." She said sighing.
I took a little time to get to know the place and realized that fully half the house was set up as Aunt Mary's dress shoppe and there was plenty of space left over. Must be nice to work at home. Of coarse, technically now I'm working from home.
I started by hauling mannequins down to the store room one at a time as I managed to make space for them. The first four were fairly normal ladies mannequins in various states of dress. But the fifth was obviously a male mannequin and it had on a bra and panties as well as high heels.
Confused by the last mannequin, I went to Aunt Mary to ask about it.
"Aunt Mary, I have a question. Why are their male mannequins dressed in girly stuff?" I asked as my aunt was busy altering some sort of dress for a client.
"Oh, I make a lot of dresses for men these days. I have several sewing forms for men around here somewhere. By the way, that's what they are called, sewing forms, not mannequins. Anyway, I do a lot of business online and there a lot of men who enjoy the finer things in life. Remember what I told you about happiness Cammy." she explained.
Well, that was a bit weird but not really. When I was at college there were school sponsored drag queen events so why not?
I decided to refrain from dragging anymore sewing forms, as Aunt Mary called them, down to the store room and just concentrate on clearing off the bed so I would have a place to sleep tonight.
What a frilly nightmare. Panties, skirts, dresses, slips, bras, stockings and every manner of girly frills. I actually got hard boxing some of the stuff up and that made me think of the male sewing forms and the people who bought those dresses.
I looked around and it didn't take long to see a male sewing form that was probably my size and it had on a short skirted maids dress that did little to hide the panties it was wearing. Frilly things covered with rows and rows of lace.
I went back to cleaning off the bed getting ever more excited as I did.
Finally when it was cleaned off and all the girly things were in boxes, I decided to take a break. It was well after noon when I had arrived and a good deal later now and I was hungry.
Aunt Mary had made sandwiches for dinner and as I ate them all I could think about was the sewing form with the maids dress and frilly panties.
"Do you mind if I knock off early today Aunt Mary. Riding on that bus was tiring and I'd just rather be done with today and hit the sack? I asked wondering if I could have some alone time with those pretty and frilly things all over my new room.
"Absolutely, you must be exhausted. Get some rest and start up again after breakfast tomorrow."She said.
I quickly went up to my bedroom and after making sure my aunt went back to her business, I carefully stripped the maids dress off the sewing form. It was more than a dress and came with a flared out underskirt which is what made the panties visible.
I stripped naked and put the outfit on. My dick got hard as a rock immediately. The shoes were just a tad too big for me but I still wore them just out of curiosity. There was no mirror in my room so I had no real idea what I looked like but I did wonder about men who liked to wear a dress.
Were all crossdressers gay? I didn't know but I suspected that many were. I looked around the room for another male sewing form and found one by the door wearing only a bra along with stockings and a garter belt. This sewing form was bigger than I was, in fact many of the ladies sewing forms were bigger than I was. I wasn't a particularly big person, rather the opposite.
The sewing form wasn't anatomically correct or anything like that but I did wonder what that must be like. I knelt down in my borrowed maids dress and tentatively placed my face where the cock should have been and gently stuck out my tongue and licked it right in the crotch.
And the door swung open and my aunt walked in carrying an armful of linens for the bed.
"I was just... Um... I mean... It's not what... I'm sorry." I stammered embarrassed as I quickly got to my feet only to trip in the heels and land on my ass with skirt up and panties exposed.
"I'm so sorry, I was just playing around." I said continuing to plead.
"You don't need to apologize or be embarrassed. Remember what I told you about happiness. Do what makes you happy and you'll never regret it." she said as I struggled to my feet then added, "I just thought I would bring some clean sheets for the bed."
I took the pile of folded sheets and noted right away they were made of silk and said, "Um, thank you Aunt Mary."
"You do look pretty in that getup. Maybe I'll have some work for you if you'd be interested in modeling a dress from time to time. Go ahead and get your bed made up and I'll be back in minute. And never be afraid to be who you are dear." she said leaving me alone but with the door open.
My heart hadn't beat in nearly a minute I was so scared.
I kicked off the heels before I made my way through the assorted clutter back to my bed so I didn't accidentally fall again but kept the dress on while I made up my bed as I thought it would be worse if Aunt Mary came in while I was changing or even naked.
I was halfway through making the bed when she returned and I was glad I hadn't decided to change yet. She would have caught me naked for sure.
"Here you go. I have four for you to choose from and a little surprise for your friend over by the door." she said as she handed me several nightgowns. She then left.
Holy shit, here for less than one day and busted playing dressup. I sat on the bed to calm myself. Well at least she was okay with it although I would never be able to look her in the eyes again.
I finished making the bed and decided to take off the maids dress but kept the panties on and then pulled one of the nightgowns, a pink one that was very short, over my head.
I looked at the small box that was a little larger than a shoebox which contained whatever Aunt Mary said was for my 'friend' by the door referring to the sewing form whose crotch I had licked.
I opened it and inside was a leather harness with an attached silicon cock. I recognized it as a strapon.
I guess she really was okay with it. I had never even considered doing anything remotely gay or in a dress and here I was about to...
I went back the the sewing form and with a little difficulty fastened the strapon onto it. I then knelt down again and gingerly kissed it before taking it in my mouth. I felt so submissive and somehow it felt good. It felt right.
I wondered what it would feel like in my ass when I heard... Knock, knock.
I stopped sucking and hurried back to my bed and got under the silk sheets before yelling, "Come in."
She came in and I saw her eyes go to the sewing form with the strapon right away.
"Would you like to talk?" she asked, how long have you been hiding this?"
"Well, actually this was the first time I ever put on a anything girly. I was just curious and the whole room was full of stuff making me excited." I explained.
"I see. Did you like wearing a dress then?" she asked.
"Yeah, I guess." I answered.
"And tell me, did you enjoy the toy for the dress form?" she inquired further.
"My jaw got sore after a few minutes." I said.
"Lots of girls complain about that but in truth it's not a big deal as most men finish way to quickly for your jaw to get sore. Did you wonder what it would be like to have it in your bottom?" she asked almost like she was talking to her own daughter.
"I guess, maybe." I answered honestly.
"Okay then, I'll be back in a few minutes and show you." she said and left again leaving the door open.
When she returned she carefully sat at the foot of my bed and said, "Okay young lady, off with the covers and lift your gown for me."
I pulled the sheet off revealing the short nightgown I had chosen to wear. She then gently pulled my legs apart. I thought she was gonna stick a butt plug or a dildo in me but instead she lifted her skirts revealing a strapon of her own with the cock pointed down. She turned it halfway and now it was erect.
It was smaller than the one she gave me to suck on, long but very skinny, and she placed it at my ass.
She lubed me up with a single finger and then entered me with the silicon dong. It was so skinny that it hardly hurt but my dick was once again hard as a rock. I moaned loudly as my violation proceeded.
"Now just remember, when your wearing a dress, that's not a penis anymore, it's a clitoris and your bottom is a pussy. Now say it for me?" she said as she began to move in out out of me in a fucking motion.
I grabbed my dick and said, this is my clitoris and your fucking my pussy.
I stroked myself about four times before I shot my load all over the nightgown and some of it got into Aunt Mary's skirts as well.
What A thrilling time I was having at Aunt Mary's place. On my very first day she caught me wearing a maids dress while pretending to suck off one of her sewing dummies and for my trouble, I got her strapon straight up my ass. I also got to wear any dress she had laying around that seemed to fit me as well as any other female clothing.
I was in a wonderland I hardly even knew existed.
I worked for Aunt Mary cleaning up her house and attached dress shoppe (They were one and the same) doing house chores and boxing up the multitude of girly things she had just laying around. I got to pick out and keep what I liked.
And of coarse my aunt took a keen interest in my bottom, especially when it was pantied. I did have my own clothes but as the first week wore on I found myself more and more in some sort of dress, either because I wanted to or at Aunt Mary's suggestion.
The very act of working in a dress doing house work made my little dick/clit hard all the time. That usually led to Aunt Mary plowing my ass with one of her strapons. She had increased the size once and the sensation was almost electric.
It was on about the tenth day after I had arrived when I got my first taste of a real cock. I had rather easily fallen into a nice routine of getting up and immediately putting on whatever dress Aunt Mary had laid out for me. Then after breakfast I did the dishes and began to do house chores. I had chosen to hide when one of her customers came in and she seemed not to mind this.
Until now.
"Oh Cammy dear, can you come down here sweetie?" she yelled up the stairs.
It wasn't at all unusual for her to summon me for some chore but this was the first time she did when she had company. I went downstairs to see what she needed when I suddenly came face to face with a man in his thirties. With him was another man in his early twenties.
"Oh Cammy dear, Mr Blanchard here wants to buy a pretty gown for his friend here but wants to see what it looks like before commiting. I have one that might fit you, would you be a dear and try it on for them?" she asked me handing me the gown. It was white and could easily be taken for a wedding gown.
"Sure." I said taking the gown from her and heading up to my room to change when she said, "Oh no need for that, you can change right here. Mr Blanchard can help with the buttons in the back."
I was embarrassed but excited as well so I carefully took off the pink ballerina's dress I had been wearing and pulled the gown over my head allowing the skirts to fall all over my body. The dress was just a tad bit big for me and walking proved quite difficult. Most of the dresses my aunt had me wear were short things that showed off my panties, but not this one. It came down to the floor and some.
"Here dear, try putting thes one while Mr Blanchard does you up." she said handing me a pair of four inch heels to step into. To my surprise, the shoes fit and by the time I was all done up, it fit nice except the skirt was way to full.
"The skirt is in the way of everything." I complained.
"I've got just the thing for that. Here, step into this sweetie." she said holding what I knew to be a hoop skirt. Right away I fell in love with the whole outfit. The way the hoop skirt held out the skirts and allowed me to move and swish around. I was in heaven even though I was being watched by a man.
"Well princess, would you like to get married in something like that?" Mr Blanchard said to the younger man with him.
"It's so pretty. I could get married in that but can you buy me one in pink to play in too?" the younger man asked.
"Sure, we'll call it a wedding present." Mr Blanchard said.
"Excellent, now I have to go and order some more fabric if you want two dresses. Why dont I leave you to get acquainted with my niece here. Her name is Cammy." she said and then to me, "Sweetheart, why don't you show them to your room so they can see what it looks like in a bedroom?"
I knew right then and there that my aunt wanted me to have sex with one of them. We had talked about what a real man would be like when she pegged me and now here it was.
Delicately, ever so delicately, I managed to walk up the stairs in the wonderful bridal gown and led the two men into my bedroom for what I hoped would be my deflowering.
Yes I know, a week and a half in a dress regularly getting pegged in the ass is making me a total sissy but so what. Aunt Mary always says better to be happy and I was for the first time in my life, happy.
I walked into my room and was worried when both men saw some of the sewing forms wearing strapons I had been using to practice on.
"Perhaps you'd like to see how the dress looks on me when I am in bed?" I said suggestively.
"Yeah, we'd like that." the younger one, the one who was to be the bride, said.
I carefully managed my skirts and got up on the bed and then laid back and said, "Want a closer look?"
I was practically whoring myself but I wanted it bad even though I had no real idea what it would be like other than the peggings I got from Aunt Mary.
The dominant one stripped naked and got on the bed and I instinctively spread my legs for him in an open invitation.
"Are you ready to see what I'm gonna do to you on our wedding night princess?" Mr Blanchard asked his friend.
"Yes, daddy, show me please." the kid responded.
He grabbed my legs and quite brutally ripped my panties down and in one solid thrust, plowed inside me balls deep.
"Ahhhhhhhh, Help, your too big. Oh fuck it hurts. Please stop." I screamed and even as I did, my own clitty betrayed me by bursting forth with a gush of cum into my skirts ruining the dress.
"Damn sissy that's a tight pussy you have there." he said as the pain of the initial violation subsided.
On my back with him holding my legs up with my panties around my ankles he proceeded to fuck me hard and soon I was rocking in tune with him. He fucked me while his so called fiance watched.
"Damn girl, if you ever wanna make some money, I know lots of guys willing to pay for a sweet whore like you." He said as his sperm left his manhood to swim around my insides.
When he was done he dismounted and before they both left, I asked, "What about him." The only answer I got was when Mr Blanchard pulled the younger man's pants and panties down showing me he was wearing a chastity cage.
"Bummer." I said as they left leaving me on my bed.
After a little time to get over the feeling of getting my first cock up my ass, I got myself together and gingerly walked back downstairs being careful not to trip in the high heels and massive skirts.
"Well, how was it?" my aunt asked.
"Wonderful but a little brutal at the beginning. He called me a sissy and said I could make a lot of money as a whore. I'm afraid I ruined another dress." I said.
"No matter, that was an older one and it was used so I could never sell it anyway." she replied.
"Aunt Mary, can I really be a sissy whore?" I asked sincerely considering the possibility of making money by getting fucked.
"Your well on your way but a whore and a sissy are two very different things. You are already a maid and a good one and were a crossdresser till you had sex and became officially gay which makes you a drag queen and anybody can be a whore by selling themselves but a sissy, that's a different matter entirely." she explained.
"What do you mean?" I asked genuinely confused and added, "I thought wearing a pretty dress all day made me a sissy."
"Not even close dear, a sissy is neither a man or a woman but like I said, something else entirely. You see a sissy is property not a person. All sissies are happy being sissies but none are ever allowed to be independant. Many sissies are kept in servitude their entire lives, made to wear a dress all the time no matter what, have sex when they're told, not when they want to and many are even kept diapered all the time to prove they are useless at anything but as a sex toy. But in exchange for being a sissy they are coddled and pampered their entire lives wanting nothing except to please her master or mistress." She explained.
"Can I be a sissy and whore at the same time?" I asked excited by the prospect of being coddled and pampered all my life.
"It's possible but you would need to find a master you trust because you will almost certainly be kept in bondage for a long time to make sure you do not escape." she said.
"Well, couldn't I stay here as your sissy and you could sell me as a whore. I'd still be able to do housework." I offered.
"Are you sure? A sissy is property like I said and I would own you. I might even sell you to someone down the line and there would be nothing you could do about it." she asked.
I like sissy things and I like you and the way you treat me and I love getting fucked.
"We'll see dear. For now I need a few things from the store. Take the car and pick up my order from Joann-Fabrics. It should be ready by now." she asked.
"Okay, just give me a few minutes to get dressed and I'll go. Should I do anything else while I'm out." I asked.
"No dear, you dont understand. Go dressed as you are. Sissies always do as they are told and live for their mistresses." she said.
Maybe I was moving a bit too fast. Getting fucked in my ass had been a thrill but...
I decided to go.