tagTranssexuals & CrossdressersThe Accidental Sissy

The Accidental Sissy

bydenontoo©

My girlfriend and I live in an apartment in small town in Texas. She a good looking 31 year old babe with a great body and sex drive to match. My girlfriend, Suzy is full figured but not fat, just a big girl and I love every inch of her.

Me, I'm 6', 185, starting to put on a little of that middle aged spread oh and I have a smallish cock. The only problem with our living arrangement is that she works nights at a local hospital and I work days, no sex week but we make up for it on the weekends.

When I'm left alone on a week night and smoke a little pot, I get horny, my mind starts to wonder and that's what happened a few months ago. What started as some simple me pleasure turned my world upside down.

I'd just kissed Suzy goodbye, she was headed out to work and I was just coming home. I was bushed. After I made sure she was gone, I got a drink and when out to the den and stripped, I'm a nudist at heart. Then plunked my tired ass down to watch TV. I reached under the night stand and pulled out our stash and took a few tokes while watching TV until I mellowed out.

About 30 minutes later I decided it was time to clean up so I went and took a shower, between my buzz and the warm water washing over me I started to get horny. I finished up my shower and dried off then headed for the closet to put my robe on I was a little chilly. It's a large walk-in community closet with shelving in the back where we kept our underwear. Suzy has one side and I have the other.

The first thing I noticed when I walked in was a pink pair Suzie's panties. I reached out and touched them, they were slick, soft and cool to the touch. At first I just rubbed them to my face thinking of the pussy that fill them up, that kick started some old memories and my with women's underwear.

I was young, maybe 14 or so at home alone. My older sister and parents had gone to some function leaving me home on my own. After they left I started snooping in Beth's, my older sister bedroom. I was young, my hormones were just kicking in and when I opened her pantie door something came over me. I grabbed a pair and ran to my room. Once there I stripped all my clothes off and looked at my prize. It was a red thong, and I slipped it on and over my cock. It was wrapped in silky luxury and the sensation made me hard. Just the movement from walking around in aroused my more. Needless to say I was hooked on my sisters underwear and before the night was over had dressed up in a complete outfit of hers. By the time my family had gotten home I'd orgasmed about three times while wearing her clothes. It was an amazing experience that happened only a few more times before she moved out but I enjoyed it very much. When she left my supply or clothing went away so went back to just being me.

For the first time since then it hit me, I had an entire closet full of Suzie's stuff I could wear. I knelt over and slipped on those red panties and they felt amazing, cool, and slippery. The material sent a charge up my cock every time I moved in them, so I kept them on the rest of the evening. It felt so amazing and stimulating wearing Suzie's panties that just before bed I jacked off having one my most intense orgasms ever.

Before I retired for the night I put her panties in the dirty clothes and pulled another similar pair to leave it in the same condition I found the first pair. I didn't want Suzy to know I was wearing her underwear.

The following night after I kissed Suzy on her way and out I went and took my shower. After wards I checked to make sure she had left then fished her red bikini's out of the dirty clothes and put them on again. They felt great and my cock started growing the instant I got them on. The I spied some of her sexy lingerie that she wears on the week end. I especially loved the purple teddy, so pulled it off the hanger, took off my panties and tried it on. It fit but not in all the right places, but if the panties felt amazing this was like being in heaven.

I wore the Teddy all night and it was delicious, my cock stayed hard till I put away the clothes and masturbated to two powerful orgasm. This soon became my normal routine, as soon as Suzie left, I'd shower put on some of her clothes and wear them for the night. Between the pot, the porno's I rented and clothes I started to fantasize that I was the women in those porno's that I was doing the sucking and getting fucked. I even started role playing by myself that I was a very naughty girl. Then one night my whole world crashed into reality.

On that particular night after Suzie had left, I showered and put on her green teddy with matching bikini's. I was gliding around the kitchen when there was a knock at my door. I wasn't expecting any visitors but I ran to bedroom put on my robe to cover up what I was wearing. I ran back to the door and looked out the peep hole, it was our across the breezeway neighbor, Dan.

Dan was a single man who had move in next door several years ago. We've talked more than a few times, even had him over for dinner occasionally. I've been over to his place to watch football games, play poker etcetra and he seemed pretty nice but slightly arrogant. When he was here he always seemed to be flirting with Suzy but she said wasn't interested. I remember he'd seen me come home so he knew I was there. With dread I made sure my robe was covering everything and opened the door. It turns out he was making his dinner and realized his milk was old so he wanted to borrow some of ours. I told him no problem and he followed me into the kitchen. I pulled the milk out of the fridge and filled his container. When I turned to hand it to him he was staring at me funny.

I looked down and robe had come open giving Dan more than a glimpse of what I was wearing. "Well, if I'd known this sooner I'd have been over here first thing tonight. Those your clothes sissy or do they belong to that pretty girlfriend of yours"

I put the milk down and tried to cover up but the damage had been done, I was so embarrassed. "It's not what you think," I stammered. "I'm not gay or anything."

"He looked at me menacingly, "I asked you a question, are those your clothes or do the below to your girlfriend, you will learn to answer me when I asked a question," and he reached out and slapped my face.

My check stung, I couldn't believe he'd just slapped me, "They're hers," I squeaked out, rubbing my cheek.

"Does she know you're wearing them," he asked in a calmer voice.

"No, no, I just started trying them on a few months ago," I said in defense.

"Well then," he whipped out his cell phone and said, "then I guess you wouldn't want me to call her and tell her what I've found out about you, or do you care"

"Please, please don't tell her."

Flash. Oh my god he just took a picture of me with his phone.

"I don't have time tonight, but I'll be back tomorrow around 6 PM, be sure your dressed in something sexy. Don't even think about not letting me in, or ignoring me, these no telling where this picture might end up," and he laughed and walked out the door taking his milk with him.

I just stood there in shock for few minutes trying to cope with everything that had just happened. I'd been caught by neighbor wearing my girlfriends clothes and he somehow enjoys having me at a disadvantage. My girlfriend would drop me like a rock if she saw that picture. So I decided my only option was to do as he says. That night as I lay in bed thinking about getting caught and seeing Dan tomorrow made me so horny I didn't think I was going to survive my orgasm.

=====

The next evening after Suzy left, I took my shower, dressed in a sexy teddy with a sheer robe, ate my dinner and waited for Dan to arrive. I had just enough time to finished up the dinner dishes sit down and grab a toke or two before there was a knock at the door. I went to the door and peered out the peep hole, it was Dan and he was dressed a little nicer than usual. I opened the door and let him in, I couldn't look him in the eye, I was so embarrassed being dressed this way. I closed and locked the door turned to go sit and stood facing Dan who had not sit down.

"Well what should I call my little slut girlfriend, I know how about Brandy." I turned beat red. "Brandy why don't you make us a couple of drinks. Then we can sit back get better acquainted." He turned and head to the entertainment center and yelled out. "Brandy where do you keep your porn."

I poked my head out the kitchen and directed him to it, he fumbled through the video's while I made two Long Island Ice Tea's. When I walked back into the Den had a porno on and was seated on the couch, I handed him his drink and turned to sit in my chair and he said, "No" and slapped the cushion next to him several times, "right here."

As I sat down next to him he put his arm around me a pulled me close, "I know you like to dress like a slut but can you please like one," and he laughed. "So how long have been wanting to be a woman," he pulled out a joint light it up and passed it to me.

I took a hit and passed it back, "It's not that I want to be a woman, I just find the clothing to be erotic to look at and wear."

"And when you wear Susy's clothes, do you masturbate in them," he said sceptically.

"Yes," I said quietly. This conversation was getting very personal.

"And when you stroke that tiny cock of yours dressed in Suzy's clothes, what do think of that gets you off," he said with a smile.

I didn't know what to say, and was struggling to come up with an answer when he said, "Do you think about being that woman on the screen."

I looked up and she was sucking a big cock and it looked like she was really getting into it.

"Experiencing everything she's experiencing, isn't that what you really want, why you wear Suzy's clothes. You don't have to answer that question the answer is obvious," and he slipped a hand into my teddy and started massaging my right man boob and nipple. "Here, this is what I want you to re enact this, and with his free hand picked up the remote and jabbed a button.

The picture on the TV changed to this hot, sexy woman dressed in a black sexy teddy with garters and matching black hose and heels walking into the living room. On the couch sat an older executive type. She walked over to him, kneeled and opened his belt and pants fished out his cock and started sucking it.

He tweaked my nipple and said, "Your turn sweety, why don't you walk in from the door and give me your best flirty Brandy walk."

I was so caught up in what was going on that I couldn't help myself. I walked to the door then sauntered back to him and parted his knees and dropped between his legs. It was strange to be unbuckling a belt from this direction, but I did and unbuttoned and unzipped his pants.

"Let me help you with that Brandy," and he stood and kicked off his shoes and slid his pants and underwear off in one fluid move.

His cock was thick and veiny semi erect mass of man meat. He said back down, spread his legs, moved his ass closer to the edge of the couch and said, "Here ya go baby. Show daddy what my little slut wants."

I had thought about playing with another cock even sucking it and it was a turn on but I'd never imagined it would come to pass. Just a few inches in front of my face was a 6-7 inch cock, starting to get hard and it had my name all over it. I reached out and tentatively grabbed it, it felt so soft but firm at the same time. I started jacking him feeling his cock skin slide up and down his shaft and it got longer, thicker and harder.

"Kiss it baby, make Daddy happy," he said in strained voice as he leaned forward and grabbed the back of my head pulling me to him.

A small wet spot had formed on top of his pee hole and I bent forward and kissed his cock. His precum stuck on my lip and as I pulled back a string of precum formed between his cock head and my lips. I brushed it off with my tongue and noticed a very sweet taste. I bent forward again taking his entire cock head in my mouth and sucking more of his precum out.

"You know what Suzy does to you when she gives you head, do that to me now."

I started emulating Suzy, pretending I was her giving me head. I licked, kiss and sucked his cock and balls for the next 15 minutes. Then I noticed his breathing had turned a little ragged. He grabbed my head forcing all the down on his cock, then slowly started to fuck my face. He pinned my head as his cum flooded into my mouth. I swallowed as much of the salty fluid as I could so I wouldn't make a mess on the floor. When he finally finished coming he had me squeeze and suck his cock till all the come was gone.

"Not bad, for a first timer but you'll get better with practice," he said quietly. Then he stood up, put on his pants and shoes and left without so much as a word.

As he closed the door behind him, I was sitting on the floor leaning against the couch, wearing my girlfriends lingerie and neighbors cum. I could still taste him in my mouth. I sat there for the longest time wondering what I'd gotten myself into.

******

The next evening when I got home from work, I went through my usual routine after she left, of cleaning up and putting on some of her lingerie, it just felt so good and sexy to have them on. I chose a black teddy with matching garters and hose. Just as I finished attaching my last clasp on the garters my cell rang, I picked it up and display said Dan. I flipped it open, 'Hello"

"Are you dressed, Brandy, his voice demanded

"Yes"

Go open the front door and let me in

I did what I was told, when I opened the front door he was there and walked in, kicked off his shoes, stripped from the waist down, except for his socks.

"Do you have a towel," he said.

I went back to the linen closet and grabbed a soft bath towel and took it to him. He laid it out on the couch and sat down, leaning back with his legs slayed open.

"Well, what are you waiting for Brandy, get on you knees and suck my cock. But this time, no hands and then we'll see how long it takes you," he laughed.

I was embarrassed, but so excited at the same time as I crawled between his legs and took his cock in my mouth.

And so my training started, every evening when I got home and dressed up Dan would show up for his nightly blow job. I did get the weekend off, but by Sunday I found myself thinking about his cock. Suzy and I were still having our mind blowing sex on the weekend, we must have fucked and sucked each other 8 times before Monday rolled around.

The following Monday, I raced around getting ready for him I was wanting his cock so bad. Just as I was sitting down to wait the phone rang, it was Dan.

"You dressed?"

"Yes," I said softly

"Good, throw on a robe and get over here." with that he hung up with out giving me a chance to protest.

I was really nervous about going out dressed even it was only next door. But I put on my robe and house slippers and walked over quickly. I felt like everyone was watching me as I walked along. Just as I was about to knock on his door he opened it and invited me inside. He took my robe and instructed me to wait in the den.

While he took my robe back to the bedroom I felt more exposed than ever. I was dressed in my girlfriends lingerie as a slut in another man's apartment. it was worrisome but at the same time very erotic. He returned naked from the waist down and sat on the couch.

"Come over here Brandy," and he pointed between his legs.

I did as I was told and started to reach out and take hold of his semi flaccid cock when Dan said, "Ask for permission, Brandy."

I was startled a little but said, "May I suck your cock please, Dan."

"Did you miss it this weekend, Brandy, and be honest. Did you think about my cock while you were having sex with Suzy?"

I didn't look at him but I shook my head yes.

"I'm sorry, I didn't quite hear that, he said"

"Yes, I thought about your cock this weekend."

"So you like being my submissive slut and sucking cock is that what I'm hearing."

My cheeks were burning from the embarrassment, but it was true I really did enjoy it, "Yes, I do."

"But we don't want Suzy to find out, do we," he said with a smirk. "And you'll do anything I say to keep me from blabbing to Suzy what kind of slut you really are."

"No, no please don't tell her and yes I do what ever you want."

He looked at me for a long second then said, "If I wanted you to suck another cock so I could watch you'd do that too."

"Yes, if that's what you want."

He yelled out, "Hey Frank, come on out, she'll blow you too."

Report Story

bydenontoo© 10 comments/ 67499 views/ 35 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartSheerrear, lilsubjimmy and 33 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous06/19/14

So hot!

My personal fantasy! Im rock hard just typing this. More please!

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by BrendaNW04/20/14

very nice

love to be brandy.. but I would dress fully with long hair and makeup..

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 10 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel