Confessions of a Re-Formed Pervert Pt. 01

I love feedback and eligibility. This is Part I of a two-parter. This part is light but the next will be considerably darker before things clarify for our hero/heroine.

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I was returning from taking X-Rays of Mrs. Rappaport's bicuspids for evaluation when Waverly, one of the other hygienists at the Delta

Dental office in Tacoma where I worked pulled me aside and had me follow her to the ladies room. She said, "Di, you'll never believe what Marshall Arrington did. He's such a pervert!"

Always up for some good dish. I replied, "He's the new dentist from Yakima, isn't he? I thought he was rather cute. Of course, at my height, I always notice guys who are taller than me especially when they are around my age. Most of the new dentists seem to be straight out of dental school, especially the women."

"True enough," replied Waverly, "but I don't think you should get too close to Arrington. Let me tell you the latest skeevy thing he did.

You know the files above where Barb sits on the 3rd floor." I nodded as she continued, "Well, Barb was home sick today and Eve was leaning over

Barb's desk. Without saying a word, that creep snuck up behind her and reached up to grab a patient's file. But then, he mumbled something about it being the wrong one and reaching deeper to it back, pressed right up against Eve's butt accidentally-on-purpose and leaned in so she felt his thing press against her. Then he stayed there fingering the files until he found the one he wanted and removed it. Took his sweet time too so his dick must have enjoyed the feel. Is that gross or what? I think he's older than Eve's father!"

I barely stifled my inward chuckle. But how could young Waverly possibly know that she was sharing this dish with someone whose infamy as a pervert became legendary in the state of Connecticut? My mind drifted back to 1962.

1962 -- Me and Cousin Joanie

Cousin Joanie lived with my grandmother since her father (Grandma's sister) and mother died in a car accident. Joanie was 7 years my elder, had long raven-colored hair and a big bosom. She teased me a couple times for awkwardly staring at her boobs, but it was a loving sort of teasing. We had a rare symbiotic relationship with relatives that far apart in age. She always appreciated me for my intelligence, sensitivity, the fact that I loved listening with her to her records, and rubbing her feet while she brushed her hair. She would take me with her to the movies occasionally and I was precocious enough that I was able to help her with her math homework which she just loved. One day we were alone in Grandma's apartment because she was out with my mother playing Bingo and I had finished Joanie's trig homework. As a reward, she snuck in a small bottle of wine and we both drank from her bottle and started giggling together.

She threw her hair back and said, "I love you, Elliott. You're my favorite relative and someone I trust secrets to you that I don't even share with my best girlfriends." I smiled from ear-to-ear and kissed her on the cheek. "In fact, you are like a girlfriend. You're sweet like a girl; you're helpful like a girl; you are always giving me supportive smiles like a girl; you even sit like a girl." I blushed.

"Do you mean that as a compliment or are you trying to embarrass me?"

Joanie kissed me on the cheek and hugged me close, "It's a compliment, silly. But I also think it's true. You're just way too nice and mature to be a boy and I think you know it too. You've even done my laundry for me, even my under-things and you fold it neater than I do. Here's how I know you love girls clothes. I heard you mumble in your sleep. I heard you say, "Does this dress really look pretty on me?" At first, I thought you were talking to me but then I realized you were just talking in your sleep."

"I'll bet you'd like to wear my clothes. We could start with these pink silk panties. It's my favorite pair. I'll help you if you want." She took another swig of wine offered it to me, and I took another sip.

I blushed. "I'm right. Aren't I?" She continued, "C'mon. Say yes."

The thrill overwhelmed my embarrassment. "Oh yes, please." She handed me a pair of white silk ones that said "Thursday." Hurriedly, I removed my jeans and jockey shorts, and put them on the beautiful silk forbidden fruit. I fell in love with the feel immediately. I giggled, "But, it's only Tuesday"

She teased, "Silly girl in panties. You're my girlfriend now. I think you've been my best girlfriend for a long time we've had a chance to dress you for the part. We may as well go with a blouse and a long skirt, but first try this half-slip on. It's my shortest, so it should be just right for you. I was in 7th heaven! She removed my shirt saying, "I wonder if I still have it..." She did. It was her training bra. Before I could even comment, she fastened it on me, saying, "We'll do what I used to do." She grabbed two wads of tissues and stuffed them in there. The she had me step into a pink skirt that went about three inches above my ankles. She laughed, "This is one of my mini-skirts. It's full-length on you." Wait, I'll be right back. She went into my grandmother's room and came back with a short brunette wig. "Hold still", Joanie said. I'm glad you have your hair long so I can clip this on. There, no one could see. That's perfect, Elliott."

"Please call me Elly!" I begged.

She shot me a look of realization. "Hey. Elly, huh? You've thought a lot about this, haven't you?" I blushed. Then she smiled happily again, pausing for some more wine, "Actually, I like that a lot. Elly it is. You know, I can call you that from now on no matter how you're dressed. People will think it's just a nickname for Elliott! We'll know I'm really talking to my best girlfriend. Now sit down at my vanity so I can make you up." She looked at me in the pink chiffon blouse and at my face. "I want to use the right combination for your coloring." She used some pale pink lipstick, sort-of-rose eye shadow and just a bit of blush. It took about five minutes and seemed more like five hours. Finally, she let me look in the mirror."

"That's me. Wow. I do look pretty. And older, almost as old as you." I said half in shock.

Joanie laughed, "Elly, don't get carried away but yes, make-up and the proper clothes always makes a young girl look older." Then she hugged me and gave me a big kiss on both cheeks. She handed me the wine. I took just a small tip but was feeling tipsy and lost in this new girl world. I didn't realize I was staring.

Joanie said, "Hey, you're looking straight at my tits." I giggled when she said tits, then nodded my head.

I blushed, "Don't girls check each other out?"

She replied, "Yes, but from the corners of our eyes. It's not polite to stare. But, I'm not angry. I'm just trying to teach you to act like a proper ladies so we can have dress-up fun when we're together. You are so natural. You really should've been born a girl."

"Yes, I know. I go to bed every night wishing my dick would fall off and I can have what you have. More than anything, I wish I could grow big breasts. I love big breasts and I always felt like I should have them someday. But wishing and praying do not seem to make it so."

"Never worry about what you don't have. Just live for the moments you can enjoy. The few times when you can really be you when we know we have the time to play together. Now, we must keep this our secret. Promise?"

I kissed her cheek "I swear. You can count on me, always and forever." She cleaned me up and we played cards until Grandma and my mother came back. We got to do that three or four more times but then reality set in.

A month later when we went to see one of the Tammy movies, she got serious and told me how ashamed she was that she was helping me dress and how much trouble she would be in if anyone knew she was encouraging me to dress the way I felt inside. She said the world shouldn't be that way but it was.

I just smiled, kissed her, and said, "I have no idea what you are talking about. I just help you study and listen to you go on about boys" We both giggled. And that was that. We kept each other's secrets forever- just like we said. She went away to Vassar for college and mailed me once a week, often with intimate details on what was going on with her latest boyfriends. For the first two years, I loved these exchanges and wished I were her. Later, I still enjoyed them but got less involved as I got more involved in my own sex life.

Growing Up Elliott

Right after my Bar Mitzvah, the ceremony of manhood was quickly accompanied by early puberty. By the end of ninth grade, I knew solemnly that there was no turning back. I almost never prayed to be magically transformed into a girl anymore. My new fantasies focused on sucking on the tits of the nubile girls around me.

I found I was pretty good at basketball and played for the high school basketball team. In the showers, when I could catch a furtive glance, it seemed as if I was reasonably well endowed, maybe a bit bigger than most. Dating-wise, instead of continuing to wish I could be with one of Joanie's boyfriends, I focused on Leah Weinblatt who had the largest chest in my home room. Eventually, we both went to the University of Pennsylvania. She majored in psych, I was pre-med but eventually decided to become a Dentist.

When going to Dentistry School at Yale, I had a small apartment. Not too coincidentally, Leah decided to go for her Masters in Psychology at Yale. I think she was expecting me to propose and I wanted to but something was holding me back. The old tensions and needs started to resurface. In the closet, I kept a suitcase where I kept my personal stashes of bras, panties, stockings, and garters. When reflecting on this, I began to realize that it was because I was feeling so comfortable with Leah, being accepted as who I am, and no longer feeling pressure. I also remembered that she had teased me a couple times during and after sex that I seemed more interested in her bras than in her boobs. I decided that she was really the one for me, she could really handle who I am.

The next date, I took her to a fancy Italian restaurant dressed in my best suit, shirt, and tie and ordered Veuve Cliquot champagne. I think she expected me to propose right there. Back at the apartment, I looked at her deeply and said that I think you already know what I'm dying to ask you, but I feel it would be unfair if I didn't share something with you and I think it's best if I just show it to you now. Stay with me and I'll explain. I took of my jacket, tie, and shirt, revealing a Hanes white undershirt, then under it a white silk bra lying limp. To my surprise, she smiled and giggled, "Could you think I didn't know you had a lingerie fetish? You did everything but advertise it on a billboard!"

"It's okay?" I asked.

"You don't want to be a woman yourself, do you?"

I looked earnestly into my eyes and shook her head no, really thinking to myself, "Well not most of the time anymore so that's pretty much the truth, isn't it?"

She then asked, "Now, is this just private and something we can do to spice up our bedroom? If you need to go out dressed like a woman, I would have a MAJOR problem with that."

I said, "No, I swear. I don't even do outer garments or shoes or anything, just the underneath stuff."

Leah then confessed she had he own lesbian fantasies and if I was into pleasing her orally while dressed up in lingerie and an occasional skirt, we could really have the sex life of both our fantasies. We kissed so hard I thought my teeth would fall out.

We got engaged that night and were married the following April. Our sex lives were fulfilling both of our fantasies and more. We introduced toys and

I loved her double-ended strap-on almost as much as we both grew to love anal beads. I got a job in New Canaan and we rented a house there.

During the next four years, we had a boy, Jordan and a girl, Rachel.

We also got along well with the neighbors. In retrospect, perhaps we got along too well but at the time, that only kept us in step. During the 1970's a form of swinging they called "wife swapping" was sweeping the neighborhood. Since Leah and I had pretty active libidos, we were open to it when Tyler and Mary Ann from down the block brought up the subject at a barbecue in our backyard. Now a lot of the couples slept over at each other's houses but Leah and I found it more fun when we cross-coupling in a location we could still hear and maybe even glance over at each other. So, most of the time when the kids were dropped off somewhere, they would just come over to see if we were available for some fun. Mary Ann was buxom, just as I liked my gals and Tyler was athletic and well hung, just as Leah liked her guys so the pairings were perfect. Mary Ann enjoyed taking me in the female superior position more than Leah whose favorite position was doggie style.

One night when they rang the bell, I was in my frilly lingerie diddling

Leah's clit for all I was worth. We finished, figuring they had returned home and we'd call them later. When the bell rang again, we just through on our street clothes and answered the door. They smiled and said they knew we were home but figured we were busy so they just went back into the car to make out, then came back to see if we were up for a quick switch. Leah sang out always and off we went, Mary Ann and I to the master bedroom leaving the door open of course, and Tyler sat Leah on his lap on the couch. Taking my shirt off, felt something she didn't expect -- my bra with the falsies underneath.

She laughed and then called to her husband, "What have we here? Someone has an even more active fantasy life than we knew about." Leah laughed, realizing what happened, calling back that sometimes I liked her to call me Elly while he dressed up in bras and panties. "Falsies too, I see," Mary Ann called back.

Leah said, "Yeah, he not only likes us full-figured gals, sometimes he like to fantasize he is one."

Mary Ann was curious. "Really? We'll have to explore that. Do you have a girl name?"

Shyly, I replied, "Elly."

Without missing a beat, Mary Ann said, "C'mon Elly girl, take those ugly jeans off and show me your pretty panties!" I complied. She continued, "

"Cool. Pink satin. I like them. We'll pull them down just to your knees and let me fuck you silly." She rode me rodeo style as we had come to both love. I hear Tyler tell Leah, I'm much more interested in what's beneath your bra, and they started doing their thing. That night ended with them both sleeping over, followed by all of us rushing out to pick up our respective kids in the morning. Although all three of my bedtime companions teased me mercilessly and talked about "exploring more with me" next time, it never happened.

Two days later, the local paper did an expose on Wife Swapping in New Canaan. It mushroomed to a regional and then to a national story. People got so sanctimonious, some of the swappers turned on one another, actually naming some names. Given the new environment, we all decided we'd cut out the "Sex Capades" until things calmed down, especially since all our kids could be put at risk. A few months later, Leah and I realized our house was becoming too small for Rachel and Jordan and financially it made more sense for us to buy than to continue leasing. Leah and I moved on to Darien. Six month later, I joined a practice there.

Work and Play in the Early 1980's

The next seven years or so, our lives proceeded fairly normally, at least as far as dentist-psychologist couples go. The kids did well in school. When they got to be 10 and 9, they started spending summers at sleep-away camp. Leah and I used our flexibility sometimes to take vacations in private cabins in isolated places. She had bought me a couple of peignoirs for playing dress-up. Then one year, we did something special in a cabin vacation in British Columbia. She enticed me to go the whole nine yards with yellow and pink sundresses, one-inch pumps, make-up, pierced ears, earrings, and the works. After all, we were alone in the cabin and could role-play to our hearts' desire.

It wasn't until later that afternoon I learned my creative wife had more up her sleeves than I imagined. While I offered to tidy up, Leah drove off to by supplies. Actually, she went to a bar that was affiliated with the general store there and did not come back empty-handed.

Back at the cabin, I was wearing a new French maid's uniform I had secretly bought myself. I picked it up at a Frederick's of Hollywood when I visited my folks in Paramus New Jersey. When Leah came back, she was impressed with the cleanliness of the cabin. Then she admired my outfit, saying it was campy but cute and that we were both on the same wavelength.

Suddenly, there was a knock on the cabin door. That's when she revealed her surprise: a 6'2" guy named Jake and another 4 inches taller named Simon. The latter gent looked directly into my eyes and flashed a broad smile.

"Elly," Leah beamed, "why don't you get our guests some drinks?" I nodded, not wanting to speak. Leah understood and asked, "You both look like Scotch and soda men and we just happen to have some here. Does that suit?" I was perplexed because we just had wine and beer. Then I looked at the counter and saw a bottle of Chivas Regal scotch and Canada Dry club soda. She had slipped it there when I wasn't looking. I fixed the drinks.

Then, I said in my softest voice, "Leah, I need your help on something in the bathroom."

Leah giggled, "I thought you might" as she grabbed my hand and we trundled off. There she informed me that they knew I was her husband and that Simon was bi- and would love to introduce me to the joys of anal sex. I shivered and shook my head.

Leah said, "Well, this vacation isn't just about you. I've waited all year for this. Now, my plan is that Jake is going to be fucking me to high heaven while Simon is going to take Elly to a place she's only fantasized about when I screwed you with a cold plastic imitation. Take my word for it, darling. The real thing feels much better!"

I couldn't help but giggle back at her. I started to protest when I realized she was right on both counts and if she was willing to go to this trouble and after all the times she has indulged me, I might as well make up my mind to lay back and enjoy it. To show her I was into it, I thanked her, then told her I wanted to look pretty for my date and asked her to freshen my make-up. She happily did, then did the same for herself.

Leading us back into the living room, Leah inserted a cassette of slow dance songs she had compiled starting with "Color My World" by Chicago. While she beckoned Jake to take her in his embrace, Simon, gentle as a lamb, took me the hand and led me masterly into a slow dance. Before the next song came on, his tongue was penetrating my mouth deeply and I was enjoying his exploration. Leah and Jake made out like crazy too as I caught out of the corner of my eye and I wasn't the least bit jealous, just proud of her, happy she was getting her fantasy fulfilled, and more than anything -- REALLY TURNED ON. Jake started undressing her, then Simon kissed my hand, then asked my permission to do likewise. I could've melted right there. After he helped me out of my uniform, I wasn't ready for him to take my bra off, revealing my falsies just yet. Instead, I reached to unhook his button and unzip his fly, grabbing for his half-hard snake. I got on my knees and planted kisses on its head. Out of the corner of my eye, I saw Leah similarly engaged, planting butterfly kisses on Jake's crown.

Then Leah shouted, "Fondle his balls like I do to you; the rest should come naturally." I nodded knowing what she did to me and what felt best.

She blew me a kiss and fondled Jake. My nipples hardened when I saw that, even under my falsies. My tucked member also started stiffening but stayed put. I turned my attention to Simon's beautiful cock. I fondled his balls, swirled my tongue against the magnificent specimen while maneuvering into my mouth. I tried to go too far too fast and started choking. He pulled out, saying, "It's all right, sweet thing. I'll get you some water, lifting me to my feet as if I weighed half of what I do. I saw Leah look my way, then have Jake's big hand put her head back in place. I smiled back at her, and winked.