Being Taught To Wear a Garter Belt

BEING TAUGHT TO WEAR A GARTER BELT & HIGH HEELS

After that special Sunday afternoon, where i tried dressing fully in girl's clothing, i had managed to amass a fairly good sized wardrobe of feminine things to wear.

Within months my hidden cache' included several pairs of silky sheer panties of different styles, a Jantzen "Postage Stamp" pantygirdle, another couple of boxes of nylon stockings (all seamless) a nylon full slip in semi-sheer white, my first bra -also in white, and a sheer pink nylon babydoll nightgown.

By now there were some weekend days when i wore panties all day long and at night would sleep in one of my nightgowns.

At about this time i asked a classmate out on a date. We really hit it off and i was fully enamored with Alice. She was very pretty but quite flat chested, being only an A cup i later learned. The other guys really liked how she looked but sought out the girls who were more fully developed. It was a great opportunity for me to get to date her.

For her part Alice was as intrigued with me as i was with her. Within a few weeks she decided we should be "going steady". Instinctively, she recognized my submissiveness.

One night we were parked out behind a vacant barn necking in the moonlight. i was in my usual blue jeans, short sleeved shirt, and loafers while she was wearing a white satin blouse and a black pencil skirt with dark hose and flats. Things began to heat up and she suggested we get in the back seat of my old car. Before long we were both at a fever pitch and i timidly began to feel her breasts through her blouse.

It was disappointing when she grabbed my wrist and prevented any further exploration of her small soft breasts. "Darling," she muttered in the moonlight, "You can go further but first we need to set some rules."

Like any teenage boy i was eager for whatever "rules" she wanted if i could continue feeling her up, so i nodded an "okay".

"I've noticed," she began, "That you pay far more attention to me if I'm wearing my most feminine clothing. You are fun to be with while I'm clad in jeans and sweatshirt and tennis shoes, but you are far more amorous when I'm dressed like tonight. Also, when we are in a department store you keep sneaking peeks at the lingerie items when you think no one notices. I think you have a 'special' fascination with girl's clothes."

i didn't know what to say, and she continued, "It's okay. I think you'd like to be able to wear what I get to wear, wouldn't you?"

Now i was stuck and she wouldn't let me off the hook. She kept prodding me and finally i had to admit what she noticed was true.

"You know what?" she asked. "I rather like that," she said before I could answer her.

"Therefore, Darling," she said, "If you want to feel my bare breasts or any other part of me you have to be willing to try wearing whatever garments you take off of me."

i couldn't believe my ears! This was wonderful, but she was a lot smaller than me.

"Agreed?" she asked.

In the darkness i could only meekly nod my head.

Before long she let me take off her blouse and then her brassiere. Guiding my head to her nipples she soon had me feeling one breast as i happily learned how to suckle the other to her extreme pleasure.

At the same time she had my cock out of the fly of my jeans and was slowly jerking me off. "You know, Darling," she whispered quietly in the darkness, "You are too big to fit in my blouse or bra so we need to work out a different arrangement."

Soon she was sliding her tight skirt and half slip up her legs and having me help her out of her sheer white panties. Then she made me take off my jeans and jockey shorts and put on her silky sheer white panties. My 7+ inch cock was straining so hard against the silky material it was hard to get them in place.

Soon she was rubbing my cock through the panties as i fondled her breasts and suckled on her nipples. Alice was moaning in pleasure but had additional ideas in mind for me.

"I've seen yours," she murmured, "It's only fair you see mine." With that she spread her legs as she slid her skirt and half slip up above the tops of her nylons. In the shaft of moonlight coming through the window i was treated to my first close up view of a pussy.

At this point Alice gave me a lesson in how to please a girl properly. How to softly rub the top of her mound and around the sides before slowly, and gently, exploring further and how to wet my finger and tease her clitoris. Within minutes i was sliding a finger in her love channel and she was really getting worked up. Her stroking of my pantyclad cock was driving me wild but i was happy to keep pleasing her.

Then she taught me how to go down on her sweet mound. Soon I was licking her clit in moonlight coming in the car windows. She had me eating her tasty pussy until she had a strong orgasm. Her nylon clad legs wrapped tightly around my head as she held me close to her while she shuddered through her climax.

I found myself quickly wanting to be going down on her pussy forever!

Afterward, having recovered from her orgasm, she sank dreamily back into the back of the car seat and smiled at me.

"I'm so glad we did this," she whispered and then leaned forward to kiss me deeply. i know she could taste herself on my lips. "It was so wonderful for me and you look so sexy and darling in a pair of panties."

Not knowing quite what to say i remained silent but must have nodded my agreement.

Glancing at her watch she realized she had to be home shortly. "Hurry, help me get dressed," she told me and I began slipping the panties down my legs.

"No, no," she said, "Keep them on. I want you to always wear panties on our dates from now on. We'll need to get you fixed up with a wardrobe of panties."

i was thrilled and happy to keep them on. Helping her put on her bra and blouse i was starting my first lesson in becoming her maid.

Driving back to her house she had my jeans open and was feeling my cock through the panties.

"You'll always wear panties when with me from now on, okay?" she asked.

Again i could only nod my agreement as she kept feeling me up. It was difficult enough driving while she was doing that to me let alone answer intelligently.

Finally, as we neared her house, i blurted out, "i have a few pair of panties at home."

At this Alice laughed and told me i had confirmed her suspicions. She quizzed me on what all i had in my wardrobe and said we'd soon have to get me fully dressed as a girl for her. i loved that idea!!

i walked her to the wrap around porch at her house and we stood in the shadows of the street lamp at the side door. Kissing me deeply Alice undid my jeans and let them fall to the porch floor as she embraced me. Then, wrapping a leg around me she began to hump her bare mound against my panty covered cock while kissing me.

"Like this my sweet pantyclad boyfriend?" she asked as she humped away at me. Before i could answer i flooded the panties with cum!

"I guess you did like it," Alice whispered, knowing what i'd just done. "We'll have even more fun next time!"

She kindly helped me pull my blue jeans back up in place and told me to rinse out my new panties once i got home. She also told me to wear just panties under my nightgown that night when i went to bed and to think over our evening together. I was so glad I'd confessed to her about my wearing girls things.

i did as she told me. Knowing what i liked she now was putting together a plan.

The next weekend we went to the local theatre to see a movie. In the dark confines of the movie house she slid a hand inside my slacks to make sure i was wearing the white panties she had given me. Smiling at me, in the dark, she mouthed that she was pleased with my compliance and then kept her hand there during the entire film, softly feeling and squeezing me during the movie.

By the time we left the theatre i had a raging hard-on in my slacks and had to walk carefully so it wouldn't be noticed - much to her amusement.

That night she had me go down on her again and told me, while i was doing so, that the next time, if I wore nylons, my girdle, and bra, on our date she'd return the favor. She had another strong orgasm, and then proceeded to jack me off to a shuddering climax.

We went out the next night, a Saturday, and i showed up at her house wearing my Playtex open bottom girdle, seamless sheer nylon stockings, a white cotton bra, and my pink flare leg panties. Alice greeted me at the door with a questioning look in her eyes.

My nodding that i was wearing what she wanted me to brought a smile to her face.

"Take your car and park it in the park," she informed me, "Then come back to the house and enter through the garage. My parents are out for the evening and my sisters are at our grandparents. We've the house to ourselves and I want you to have fun."

It didn't take convincing to have me move my car and I was quickly back inside her house. Alice was waiting for me in the living room when I entered, wearing only a white garter belt, dark brown seamless nylons, dark brown four inch high heels, and sheer white brief style nylon panties.

"Take off those yukky boy's things," she instructed me. "I want to see what lingerie you wore for me.

Soon i was nervously standing in her livingroom wearing just my open bottom girdle, dark cinnamon seamless nylons, sheer pink flare leg panties, and my white bra.

"You look so cute dressed this way," she whispered as she embraced me and gave me a long French kiss. "Your panties are tenting despite the girdle you have on. I love it!" she said as she broke the kiss.

"However," she hastened to add, "You really need to think about wearing a garter belt to hold up your nylon stockings. They're way more comfortable and, in your case, won't get in the way of when your 'cockette' wants to stand up proud."

At this point i confessed i had often thought about a garter belt but knew should it be listed on my "employee purchase" list at the shop the SKU number would cause notice since my mother obviously didn't wear one.

"I've seen you looking at them in the stores we've been shopping in," Alice told me, "And I'm convinced you'd quickly learn to prefer wearing them rather than girdles. Besides," she went on, "The hem of your girdle sort of gets the way."

Looking down, it was obvious the bottom edge of my open bottom girdle did prevent me from coming to full 'attention' when aroused by what i was wearing. i did loved, and still do, the secret 'hug' of a girdle but knew Alice was right.

She took me upstairs to her bedroom. i was treated to the lovely sight of her darling fanny and backs of her nylons as we went up the stairs.

Once in her room she turned to me and directed me to begin caressing and suckling her delicate nipples atop her budding small breasts. Before long she was laying back across her bed and i knelt between her legs and orally brought her to a satisfying orgasm as she had taught me to do.

"Now for your reward, Darling," she whispered as she recovered from her climax. Opening her closet she showed me some of her mother's things she had brought up to her room.

"Mom won't miss these items for awhile, and I want you to try them on for me."

The pile included a white garter belt with four garters, which she told me should fit me as her mother and i were nearly the same build - except her mother was a lot shapelier. Then there was a white nylon full slip, a white satin bra that i knew would fit me perfectly, and a dark brown shirtwaist dress and dark brown high heeled shoes. Her mother's shoe size was the exact same as mine and the heels were about 4 inches high.

We wasted no time. Alice quickly showed me how a girl puts on a garter belt and i discovered it was a lot easier than donning my girdle that was still a struggle for me as Alice had yet to show me how to properly don a Playtex all rubber girdle.

i loved the feeling of the garter belt suspender straps sliding across my hips as i walked about Alice's bedroom and she giggled when she noticed the delight on my face. Putting my panties back on i was shown how Alice put on her bras and then she stuffed each cup with a pair of her silkiest panties. The full slip came next and i was already trembling. After that Alice helped me into the dress and buttoned up the front.

She had me sit on the side of the bed and slip into her mother's high heels and i was amazed at how nice they felt on my nylon covered feet. Having me stand it was further amazing to see how the shoes seemed to make my legs look longer and stretched out my calf muscles in a more feminine appearance. i was really loving this, but my hard cockette was clearly straining against the front of my panties, slip, and dress.

"I can see you like this," Alice laughed, "Your little dickie is showing its reaction and you cannot deny it."

Alice had me practice walking about in her mother's high heels and it quickly became apparent this would take some practice before i stopped walking like a guy. Her tips to lift my knees and then throw out my feet, with each step, instead of throwing my full leg forward unbent, helped a lot. Also, she showed me the need to take much shorter steps and place one foot slightly in line, and ahead, of the other would feminize my steps and make my buttocks sway in a more feminine manner.

Soon my strides were much more girlish and i knew i'd practice this on my own at home even if just in nylons and loafers.

i had to join her in giggling, as she kidded me about my hard on, and then she had me come over to her bed. Seating me on the side, she kissed me as she ran a hand up my nylon clad legs and massaged my cockette through the panties i was wearing.

"Like this?", she asked as she worked on me while kissing and tonguing my ear.

"Ohhhh, yes," was all i could mutter as she felt me up like i was a girl.

"Well," Darling, she began, "Since you are willing to be girl for me I'm going to show you more of what it is like to be a girl."

That said, Alice began sliding my panties down my nylons and soon they were off my legs. She slid my dress and slip up to my waist and had me lay back fully on the bed with my head resting on her pillow atop the covers. Moving up over me, Alice surprised me by suddenly impaling herself on my cockette!

"Ooohhh," i gasped as she slid down onto me and was astonished at the sensations.

"You're now my slut," she muttered as she began to move up and down on my cockette and quickly i was doing my best to meet her with thrusts of my own.

"This is your reward for dressing up fully for me, Honey," she whispered in my ear while fucking me furiously. "I think I'm taking your cherry, aren't I."

All i could muster was a nod "yes" and knew she now had taken my virginity. Alice rode me and made sure our nylons rubbed against each other until I was ready to cum.

"It's okay, Honey," she whispered as she kissed me deeply, "I'm safe right now and want to feel you cumming inside me."

In moments i was shooting hot cum into her love channel and she shuddered through her own climax with me.

Afterward we lay there, still entangled with me still in her and recovered from my first fuck. She whispered that she had lost her virginity to a camp counselor the summer before and loved fucking.

"What I love fucking the best, though, is you and when you are dressed like I am in girls things.

"Now you've a job to do for me," she concluded, "And that is to clean me up."

Saying that she slid my softened cockette out of herself and moved up over me only to lower her pussy down to my face. i immediately understood and began kissing and licking my way around her mound before centering my attention on sucking the cum out of her.

Suddenly, it dawned on me i was ingesting my own cum and it was great! Quickly i began licking and sucking her in earnest. When it seemed there wasn't anymore to get from her i concentrated on her clitoris, alternately licking and sucking gently on it until I felt her silk covered thighs tighten on my head to hold me in place while she shook through another orgasm.

It was a wonderful first experience at fucking and i was so lucky to be able to do it while dressed fully as a girl.

That evening Alice showed me how to put on make-up and we spent our time together dressed alike in dresses and high heels. Before her parents came home we fucked again with me on top and both of us wearing just garter belts and nylon stockings. It took me longer to cum, this time, and it seemed better than the first.

"We're going to go shopping together," Alice told me as she showed me how girls put on rubber girdles, while i was dressing back into my own things to go home, "And we will find a pretty feminine garter belt for you in your size. I'll want you to wear panties and garter belt and nylons on our next date after that. When you do, I promise to suck your cockette until you cum in my mouth for me so I can swallow you."

i happily agreed!!

We did go shopping and she found me a pretty lacey garter belt, in pink, that i wore the next time we went out. i loved how it felt with my stockings and panties under my boys slacks.

Alice and i soon had a schedule of meeting at her parents house when the rest of the family would be gone for the evening. Her mother learned of our sexcapades about two months later and took her own action at that time.

More about Kathleen, Alice, and me later.

Sincerely,

sissy erica