Trixie Admits Her Naughty Pleasures

When I was 24, I meet this wonderful, handsome man at my new job. I had just been hired as a third grade teacher at an elementary school in a county next to the one I grew up in here in Florida. I know I'm being a bit mysterious here but I am trying to protect my identity from getting to the old church ladies on the PTA and school board because I know it would mean my job in this backwards county.

At school I put on a conservative air about myself. The women teachers can not wear pants at all, or dresses more than four inches above their knees while teaching classes. I'm just glad they don't pull a panty check or I would really be in trouble. I hate wearing underwear and most of the time I don't! All I wear underneath my tops is a sport bra, which is fairly easy to get away with since I'm not allowed to wear sleeveless dresses or tops either.

I met Don my first work day there. I actually meet him in the parking lot when I parked next to him. He just happened to be the new vice-principal there. He introduced himself to me as he helped me carry a bunch of stuff to my classroom. I found out he grew up in this county and that his mother still teaches at another school in this county. He then reminded me that I would not be allowed to wear what I was wearing to teach in but since I was working at setting up my classroom and cleaning it was alright. And as I was bending over putting supplies away in my bottom desk drawer, he said, "But you do look good in it."

I was wearing a large tank-top with large armholes but I was wearing a bikini top under it and I was also wearing 'just' (no underwear remember) a pair of tight black yoga pants and sandals. I was bent over away from him and I'm sure he was looking at my ass in those tight pants, so I just looked around at him, and smiled while saying, "Thanks. I'll take that as a compliment!"

I stood and told him I was aware of the dress code but that I didn't want to get any of my good clothes dirty or ruined. He said that there was no problem; he just felt he needed to make sure I was aware that he knew the rules too since we were both new here. As he left, I noticed how good his ass looked in his tight jeans.

They had a get together in the school cafeteria around lunch time and introduced everybody to everybody. Don sat next to me and during lunch we both discovered we were both single and currently not seeing anybody. He asked me out for dinner that night and I happily accepted.

Not knowing that much about him, I wore a conservative but snug fitting black dress with just a small black lace bra underneath. The dress rode about 6 inches above my knees. I normally didn't wear my dresses this long; I normally wear them 3 to 4 inches below my crotch. I like them short! I was just playing it safe on what I hoped was just our first date.

You see, I am an exhibitionist. I have been for most of my life. I have my mother to thank for that, you see, she was one too!

I grew up on the east coast of Florida. I spent most of my time during warm weather in swimwear. My house was only two blocks from the ocean, plus we had a small pool in our backyard. When I wasn't wearing my swimwear, I loved wearing my bib overall jumper. From a little girl until I was about twelve, I ran around my house, my yard, my neighbor, and the beach topless, wearing only my bikini bottoms. Mom even got me a string-tie thong when I was twelve. I loved that tiny little bottom. But hated wearing tops, and I felt that since my two older brothers didn't have to wear any kind of top, why should I? And when I wasn't wearing my swimsuit you could usually find me wearing just a pair of bib overalls. My mom wore them too, but she wore her bikini top under the bib front, I didn't. She rarely wore underwear while wearing them so I didn't either. The bib top covered my chest and nipples and the shorts cover my ass. I was happy and no one complained even when I went into the stores dressed like that. I owned 3 or 4 pair of them and when they got tight and small I would get mom to buy me more. It was hard to find them in shorts length so mom would just cut them off and hemmed them up to short-shorts length for me and her.

Around about when I was twelve my breast began to swell, it still didn't stop me from not wearing a top with my bibs. I decided if someone seen my little tits, big deal! Let them look! I often ran around my house and yard topless even through high school. My two brothers never complained plus I noticed their dicks getting hard a few times when they looked at me. I wasn't sure why that was but I still kind of liked knowing I might have been the cause of it. Oh, they usually ran around the house in only their boxer shorts so I really didn't have to look hard to see their little hard dicks making tents in their boxers.

I still liked wearing 'only' my bib overall shorts in public and luckily my breast didn't get very big. I was only a 34A when I was a senior in high school, so I often went out wearing only my bibs. A person could see the sides of my tits and my bare back making it very obvious that I was braless and topless except for the bib coving my tits and the front of my chest, I didn't give a damn if people liked my outfit or not, I DID! And since my chest and nipples were covered, I wasn't breaking any laws. I also did not button all the buttons on the sides at the hip. I only hooked up the top button, leaving an opening at the hip showing nothing but skin beneath. Plus it was easy to keep cool dress like this in Florida during the summer. I eventually removed the other buttons from the bibs so I couldn't button them up if I wanted to. I liked the bare skin showing at the hip look!

I couldn't get away with wearing my bibs to school so I did the next best thing; I wore very short dresses or skirts to school. Yes, I did wear underwear to school, the smaller the better! I loved letting the boys look up my skirt. I found out early how much fun it was to tease the boys by just letting them see up my skirt. I was active in a few clubs at school. Yes, I was a cheerleader too! I guess you could say a naughty one too. I lost my virginity at 14.

Yes, the guy was on the football team and also a neighbor boy I had known for years. One afternoon during the summer, I was alone at home and was enjoying the sun and working on my all over tan by floating nude on an air mattress in our above ground pool.. When all of the sudden Weston came in the back gate, I slid off the mattress and stood up. I'm not sure if he knew I was naked but he could tell I was topless because I was standing in waist deep water and my tits were above the water. He's seen them a few times over the years but not in the last couple. He stared at them as he asked where my bothers were and I told him I wasn't sure. He then said the water looked nice. By this time he had made his way to the edge of the pool and was looking down, I guess trying to see if I was wearing anything under the water.

I told him it felt real nice and that if he wanted, he could join me. He kind of hesitated and then said he didn't bring his suit. I walked to the edge near him and said, "You probably already figured out I'm naked in here so why don't you remove your shorts too and join me. It will be our secret. I'm sure you will enjoy it." My brothers and I have skinny-dipped quite a few times over the years and seeing a naked male is nothing new for me, but for some reason my heart was pounding with the expectation of seeing Weston naked. He finally said OK and removed his shorts. I was standing next to the latter as he climbed over the pools edge and I sucked my breath in as his dick appeared over the edge. It was twice the size of my brothers' dicks and his was sticking straight out. I had never seen theirs sticking straight out like that. I had heard so of my friends talking about hard-ons, I guess this was one. For some reason I just had to touch and examine it, so I did! As I touched and stoked Weston's dick, his hands found my tits. His hands felt so wonderful, I never even thought of telling him to stop. Then one of his hands found its way to between my legs. His hand and fingers felt way better than mine ever had. Let's just say we soon got out of the pool and went to my room, where I became that naughty cheerleader.

One of my favorite memories of high school was the day they took pictures for yearbook. I dressed for the occasion. I wore my favorite short red skirt and tiny white thong panties. I had three pictures taken that day with different clubs I belonged to. I made sure I got to sit in the front row for all three pictures and surprise, surprise; my legs were apart in ALL three and my panties were visible. I now have a permanent record for all my classmates to see. I must have signed a couple hundred yearbooks next to my panty shots with an arrow pointing to my crotch. I was such a bad girl. Ha-ha.

Like I said, I did wear panties to school, but hardly any where else. I found I enjoyed going commando under my dress when I was about 12. I was dared one day by one of my male friends after school, as we walked home, to take off my underwear and walk back home without them. There were eight of us, three girls and five boys, walking the half-mile to our homes, we were all neighbors. They had all seen me topless over the years and some knew I wore no underwear when I wore my bibs. I had often wondered how it would feel to wear a dress only while walking down the road during the daytime. For years, my mom and I have walked the beach in the evenings wearing nothing but a t-shirt or tank top, but this would be in the middle of the day. So I took his dare, right there at the edge of the school property, I asked him to hold my books as I reached under my dress and pulled down my underwear. It felt invigorating and exciting walking down the public sidewalk with all my friends knowing I was now naked under my dress. I liked it and knew I would be doing it again and often.

The next day he dared me to take them off again. I told him I couldn't because I had already removed them while I was I the bathroom just before I joined them. Then I opened my notebook and showed them to him. Then he dared the two other girls to remove theirs, one did, the other refused. After that day I often remove my panties before going home, sometimes after school and sometimes after lunch. The last week of school I didn't even wear any when I left for school in the morning. I found I really enjoyed being naked under my dresses or skirts during classes. I just had to be real careful how I sat while at school.

All through my college years my exhibitionism reached new heights. I also became a total slut. I loved sex and I loved to be naked. The more people to see me naked, the hornier I was. I participated in group sex often. I didn't care if it was male or female, one, two, or more. I just liked sex.

I even let some of my friends tie me up and blindfold me for an entire weekend. They stripped me naked in a big van, blindfolded me and drove me around to who knows where. I have no idea how many people seen me naked or fucked me that weekend. I know I often had two and three dicks in me at once. They gave me food and drink, often alcohol, while still blindfolded. If I had to pee, they made me piss on the ground near the van a few times. I have no idea where I was or how many people watched. That was my worst and best weekend ever. I lost track of how many time I came but I know it was a lot! I have never done anything like that again and have no plans to go crazy like that again. Three or four men at once maybe but never gang-banged with no control or knowledge again!

Let's get back to Don now.

Don and I hit it off real good that night. I played real cool and conservative and only let him kiss me on the cheek that night. But I really wanted to rip his clothes off and fuck him silly.

The next date we did some minor kissing and he asked me if I had any shorter dresses that I could wear out on dates. I told him I had a few but I that I liked him and didn't want to upset him with wearing something unbecoming a school teacher. He said, "Screw the school teacher image, whenever I take you out on a date out of town, you can dress be as naughty as you want to be. I would love having people see me with a sexy woman on my arm." I told him that I might just surprise him one day. He smiled at me and said, "I hope so!"

Friday, while at school, he said that if I had no other plans, that tomorrow evening, he wanted to take me to a comedy club in Jacksonville and then maybe a little dancing later if I felt like it. I said it sounded like a great idea. He said, "Great, and you can wear something sexy if you want too. Or were you just teasing me last weekend."

I smiled and gave him a wink as I said, "If you want sexy, you'll get sexy. But please don't send me back home if I dress too sexy."

"Oh, now you're teasing me!" he said. "I'll pick you up at 7, OK?

The next evening I put on a black, mid-thigh, deep plunge halter dress and the only other thing I wore were black strappy sandals with 4 inch heels. I decided to be more daring around Don but still not tell him I was pantiless. That was for my on pleasure. Maybe I would also get a chance to flash someone my hairless pussy tonight. I would try and wait a few more dates before I let him see me in one of my really short or sheer dresses.

Don seemed to really like my dress. He couldn't stop complimenting me on sexy I looked. He said none of the other girls he had dated had ever worn anything near as daring as the dress I was wearing. I felt happy he liked my dress and made sure I leaned over a few times more than I needed to, just to let him have a look at my titties as the top fell away from my chest. He had a big grin on his face almost all night.

Since I'm not much of a dancer, I asked if he minded if instead, we go to the beach and walk in the moonlight at the tides edge. He said he liked the idea, so we did. We walked about a half hour before a breeze picked up and the air chilled off, so we left. Nothing else happened until we got back to my house. We started making out like teenagers in his car. The kissing definitely got heavier this time and I surprised him when I moaned as I let him put his hand inside the top of my dress on one of my bare tits.

He alternated rubbing my tits which I love. I have come before from just kissing and a good tit massage and I did with him. I think it surprised him how quickly I had an orgasm right in front of him. I then told him it was his turn to get off, as I reached for the zipper on his pants. I was surprised at the size of his dick; wrong not a dick, a cock! His cock was too big to be called a dick. It was a good 10 inches long and two inches thick. All I had planned to do was give him a hand-job but the size of that thing was making my mouth water. But I was able to control myself and give him that hand-job. After he came into a handkerchief he produced for somewhere, I told him that he had a nice penis there and someday I might do more than jerk him off. He said he would be looking forward to that day. I kissed him again and made sure he saw a lot of leg as I exited his car. I stepped in front of his car just before he backed out my driveway and whit his headlight shining on me, I pulled my halter top apart and flashed him my tits before I threw him a kiss and turned to go inside. I quickly went to my bedroom removing my dress and dropping it on the floor as I entered my room, I then got my biggest dildo from my nightstand and put it to good use before I fell blissfully to sleep.

The next day about 9AM, there was a knock on my front door. I was awake and just thinking about Don and that big cock of his as I softly played with my pussy. I grabbed a short robe from behind my bedroom door and pulled it on as I went to the front door. There was Don with breakfast from 'McDonalds'. I opened the door for him and asked why he was here so early. He said he had trouble sleeping after what happened late night and thought that maybe we should talk about it. I said I was alright with what happen and rather enjoyed it but since he brought breakfast and I was hungry that maybe we had better go to the kitchen. I closed the door and led the way to the kitchen well aware that my short robe barely covered my ass. The robe was rather thin too, so he could probably make out the crack of my ass as he followed me. This was causing my pussy to tingle knowing I was practically naked in front of this man I was beginning to have feeling for and that he probably knew I was almost naked too. I looked down and I seen my nipples were hard, producing two rather noticeable points on my chest. I turned, offering Don a chair at the table and noticing his eyes looking directly at my pointy nipples. That sure didn't calm down my pussy!

Don sat down and then noticed a table on my back patio. He then cleared his throat and said that since it was such a pretty day outside, he was wondering if we could have breakfast outside on the patio. I said, "Sounds like a good idea, but I would need to put on some clothes on because I wasn't going outside dressed like this. Go on outside and I will join you shortly." I could see the disappointment in his eyes. He was probably hoping I would go out dressed like I was in an almost see-thru outfit. Oh, I have sunned nude on my patio many times already and being naked outside is one of my favorite thing to do, but I suddenly had a good idea.

I gave him a quick kiss and quickly left the kitchen. As I walked down the hall to my bedroom, I removed my robe and hung it back on the door as I entered. I reached into the third draw of my dresser and pulled out one of my bib jumpers. I slipped it on with nothing else and left the room buttoning only the top button on each side. I walked out the back door and I seen Don's eyes get big. I said, "I hope you don't mind this old thing. I've worn this thing for years. It's very comfortable and I like wearing it. Plus I don't get hot when I wear this, at least, I mean, I don't sweat in it.

Don quickly got his composure back and said he loved it. I then raised my arms and slowly turned around giving him a good look at it from all angles. I sat down across from him and ate my breakfast and decide to tell him a few things about my youth and about how I enjoyed wearing my bibs everywhere. Praying it wouldn't shock him and make him run away from me. Then he asked, "You mean you use to wear it just like that, I mean dressed as you are now, all around town?"

I said, "Yes, but don't forget, I grew up in a beach community and a lot of people ran around almost naked. People use to go shopping and to the bank wearing only their bikinis. Going braless was the norm, and seeing girls running around topless until they started growing little boobies was normal." I took a couple more bites of my bagel as he thought about what I said. Then I said, "I hope you don't think any less of me since I admitted I normally wear less clothing than you were aware of. I am beginning to like you and I feel it is important to tell you the truth. I am a bit of an exhibitionist! But I won't dress that way around school functions and around the kids. But around the house here and away from town here, it may surprise you what I might wear or not wear."

He looked at me and said, "I am afraid I'm falling for you too, and your being a bit of an exhibitionist does not upset me in the least, in fact I kind of like it. It excites me a bit knowing the girl I'm with isn't fully dressed. But I do have a couple questions to ask you. If we left right now and went to the beach, would you really go there dressed like that and were you ever without any clothing on our previous dates.

I gave him a big smile and said, "Yes, I would go to the beach right now dress as I am but I would take along my g-string bikini in case we decide to get in the water. And yes I have gone without on our dates. I wore no panties on our first two dates and wore nothing under my black halter dress last night. I hate wearing underwear. I'm afraid that even at school, I don't wear underwear under those long dresses, but being as long as they are, I feel pretty safe no one will ever know, except for you now and I hope it won't affect my job, will it?"