A Beautiful Teacher

I was standing in the lingerie department at a major department store when I heard that voice say, "Did you find everything alright, Hon?"

It may not sound that unusual, but I'm a 24 year old guy, buying a pink bra and panty set for myself, and I knew the woman working there, she was my English teacher from high school.

I started wearing panties in my early teens and haven't stopped. In fact, I have ventured into all sorts of lingerie that I like to wear around my apartment and to bed. Panties are my passion and I appreciate a silky bra, slip and even teddies. Except for the moments when I'm wearing something silky and sexy, I'm a typical suburban guy. I went to college, moved back to my home town -- my parents moved away when I was in college -- and have a job and an apartment.

While in college, I had my share of girlfriends, some of whom I told about my panty fetish. My last college love encouraged me to wear them more often while we hung out and I loved it. Since then, I've been exploring on my own and having the occasional hook up. I have always found it hard to find a woman who would be interested in seeing a guy in lingerie, much less sleep with him, and so it is often a solo activity.

When I venture into a department store to shop for new things, I usually scan the area for anyone I might know and always have a story about buying a gift for a girlfriend as a reason for being there. Every now and then, I've managed to sneak a few panties and bras with some men's jeans or shirts into a dressing room and try them on before buying. After all, not all things will fit right on a guy, but the ones that do, are worth so much.

This was one of the times when I wasn't able to try anything on, but I had selected well enough that I knew I was going to enjoy the pink panties and silky bra that I had picked out. In addition, I had grabbed a black half slip and a few pairs of panties that I just couldn't live without.

There were some other women near the register so I didn't see who was working until I had walked up and placed everything on the counter. It was Ms. Watkins asking if I found all the lingerie that I wanted, along with that, "Hon" that I had heard all of junior year. She called everyone "Hon."

Ms. Watkins was one of the cool teachers. She dressed with class, but was never the stuffy type. Her dresses were trendy and fit her curves well. She had a great body that was not skinny, but you would never call her overweight. I scanned her ass daily for pantylines and her tops always displayed her chest with class. Her dark hair was cut short, yet feminine, and she complimented her look with dangling earrings and just the right amount of makeup. Plus, she taught us about emotions, compassion and other human conditions that made up the stories we read.

We students didn't know much about her other than she seemed to have a nice lifestyle for a teacher -- she drove a sports car and often mentioned concerts she had attended or trips she took with friends. She didn't seem to be constrained with a teacher's salary so she must have had some money to begin with.

"Jack? Jack Baker! Oh my gosh, what a surprise."

I was stunned. I acted fast and false confidently smiled at her. "Ms. Watkins!, it IS a surprise." We were both a little stunned and there was a brief pause at who would speak next.

"You've grown up!" she continued. She looked at my selection of silky, colorful undergarments as she picked up the bra to find the tag. My heart was beating through the thin camisole I was wearing under my sweater, expecting her to ask me what I was doing there. "And, you have great taste," she added without any awkwardness.

I blushed. "Thanks, Ms. Watkins" I paused. "Oh, can I have a gift box, please?" I had learned that department stores handed out flat boxes with lingerie purchases so I could buy things with the idea that it was a gift for a lady friend.

"Of course," she said with a great smile and a wink, "but call me Susan." The wink could have meant anything, but it burned into my soul. I was freaking out on the inside with embarrassment, but also a little excitement.

I paid for the items and she made some small talk about the school's sports teams and administrators that we both knew. I said thanks as she handed me the bag and I headed toward the mall exit.

"Jack," she called just as I was weaving through the juniors department with racks and racks of dresses. I turned and saw her walking toward me. Her smile glowed and I took a good look at her. Her dark hair was still short but was now more of salt and pepper than anything else. She wore a tight, wrap-around dress that made her look professional, but not too businessy.

"Jack, I'm on break, let's go get a Cinn-a-bon or something. I'd love to catch up with you." I froze. I was hoping to escape, but there was nothing I could but say yes.

"That sounds great," I said while working on a smile. I was nervous, but she was always so fun that I wanted to hang out for a bit.

We made our way to get a snack at the food court. We sat across from each other and I set the formal department store bag on the seat next to me. My mind couldn't forget about the thrilling lingerie in it, but I was also into our conversation.

As our catch-up talk wound down, she took one of my hands in hers, paused, and said, "Jack, I meant what I said about you having good taste in lingerie. The panties and bra are super cute." My heart jumped when she said "panties" and I sat on the edge of my seat. She leaned over the table and whispered, "I'm sure they will look good on you," and she squeezed my hand firmly, not about to let go.

I sat stunned and slack jawed. I didn't know what to say -- do I continue to bluff? Or, do I take the opening she is giving me? I didn't act. I couldn't move. I could feel the blue panties that I was wearing under my jeans and my matching cami slide on my skin as I squirmed.

Still whispering she said, "It's alright. I'm a firm believer in doing whatever feels right. I support you."

My palms watered with sweat. I couldn't bear it anymore. I nodded instinctively and said dryly, "thank you."

I cleared my throat as we both relaxed. Her hand loosened its grip on mine while she wrapped both hands around mine. "Why do you think... I mean, how could you tell it's all for me?"

She laughed warmly. "Oh, Hon, it doesn't matter. We see men like you at least once a week in that department. In fact, I've gotten to know a few of them, and I have always found them to be thrilling."

My spine was starting to relax as she talked. I felt so close to her after admitting my secret and hearing her talk. It made it real.

"Jack," she continued. "I have to get back to work, but let's hang out this Saturday afternoon. I'd like to talk more, I have some great tea you should try, and," she paused longer this time. "And, I'd like to see your collection." She must have known that all men who like panties and lingerie have a stash, a collection of items that they have gathered along the way. Mine was full of panties, a couple of bras, slips and other lingerie. She stood, "yes, bring your clothes and let's talk more. What's your number? I will text you." I mumbled my phone number robotically as I sat in nervous shock.

She bent and kissed my cheek as she went back to work.

I grappled with emotions on Saturday morning. Fear, embarrassment, denial, freedom and pleasure all mixed through my head. I put on the pink bra and panty set that I had just bought as I packed my collection into a gym bag.

She welcomed me in with a warm smile followed by a quick kiss on the lips as she embraced me. "I'm so glad you came over, Jackie" she said as I melted with shy, nervous excitement as I entered.

She was dressed in a simple navy dress that hugged her body and just wrapped around her full breasts. The stunner were her white stockings that she wore without shoes -- a sexy-casual look. I followed her to her living room and she asked to take my bag as she instructed me to sit on the couch. I obeyed and watched as she set my bag on the low coffee table and sat next to me.

We talked for a bit and had a few sips of wine when she reached down to rub my thigh gently as she asked, "Are you ready to show me your things, Jackie?" as she motioned to the gym bag in front of us. I was starting to pick up on her "Jackie" instead of "Jack", and thought it was a nice touch.

My heart skipped a beat. I nodded, cleared my throat and said, "Yes. Yes, I think I am."

"I thought so. Why don't you start by showing me all the lingerie in your bag and then I can pick out my favorites," she winked and sat back. I looked at her as I stood up and her nipples were rock hard against her tight dress.

I laid out all the lingerie I had collected -- all of it -- the panties of every color, bras, body suits -- all of it there on the table and couch in front of my favorite teacher. I stood in front of her when I had finished and she stood up to be face to face with me. She took my hands in hers and held them against her thighs as she looked into my eyes, "Jackie, thank you so much for sharing this private part of you. I enjoy seeing this side of you." She kissed me deeply and wrapped her arms around me. We kissed and felt each other bodies. She inhaled deeply in our kiss as she slipped her hand into the back of my pants and felt my panties.

She hugged me tightly and whispered in my ear, "Oh, Jackie, I think I'm going to like this a lot. Now, take that white bra and panty set and let's go into the bedroom to see how they look on you. Come," she said forcefully as she ended the embrace. I stood for a moment to let it all sink in. My cock was hardening and my heart was pounding as I followed her.

She sat on the edge of her bed and watched me get undressed. Her room was feminine, airy and had a large mirror leaned between two windows that looked out toward her small back yard. She had grace in everything she did and I felt comfortable as I exposed my body and my panty covered cock which was bulging with anticipation.

"Oh, I do like the pink set that you just bought. I'm glad you wore those," she said as I took off my shirt. "I couldn't even see the bra straps under your shirt."

"Thanks, Ms. Watkins," I said.

"Hon, call me Susan. Now, let's see you in white."

"Mmmm, wait a second," she said as my panties came off. She knelt in front of me and held my cock to her mouth. "It's beautiful, Jackie," she then took my cock in her mouth and sucked on it for a few minutes. Her index finger quickly landed on my asshole and she gently applied pressure while I moaned with pleasure.

She stood to kiss me while leaving her finger caressing my asshole and said, "Your cock may be ready, but I'm not. Let's continue with our dress-up game, Sweetie." She returned to the bed while I slid the panties up and tucked in my penis. Luckily, the panties were high enough to contain me and tight enough to hold my cock against my body as I reached for the bra. Once I had the bra on, I turned to show her.

"I usually stuff the bra with some panties," I said. I sometimes enjoyed being large breasted and would fill bra cups with a large handful of silky panties. This bra was a B cup so just a pair or two in each gave me a great shape.

She examined the fit of the panties by rubbing my ass and a long caress of my cock. "You look so pretty, Jackie. Do you enjoy looking so feminine?" she asked.

"Yes," I said shyly and held my hips with my hands for support as well as to pose, "I love the feel of the panties, and the bra makes me feel sexy." The sunlight in her room was warm and I looked at myself in the mirror. She stood behind me and our eyes locked in the reflection.

"You look very feminine. I'm going to have fun making you my girl," she said. She was taking me much farther into femininity than ever before -- calling me Jackie, and "pretty" -- it was all a turn on. I trusted her as the teacher she continued to be.

She ran to her closet and was back in a flash with a blonde wig. "Try this on. Let's see how Jackie looks as a blonde."

I put the wig on and looked in the mirror. I recognized the outfit and my face, but the wig made me feel like someone new. I ran my hands up and down my sides and to my breasts feeling my new shape.

"Oh, you look fabulous, Jackie. I could eat you up you are so cute," she said with a smile. She came over and kissed me deeply on the lips, pulling me close to her. My panty covered cock rubbed against her dress and we started making out.

She paused for a minute and said, "let's try one more thing." She undid her wrap around dress revealing her body. She had a bright white bra, panty and garter belt set that made her look like a model. "You can see why I wanted you in white," she added as my mouth hung open with desire.

"You are amazing," I said as I recalled all the times sitting in her class trying to undress her in my mind. Here I was with both of us in our underwear and me in her wig with a raging hard-on in her bedroom.

"Put this on," she instructed as she helped me into the dress. "We have similar builds so it should fit you."

I wrapped the dress around me and adjusted it around my breasts. It covered the bra completely and showed off my upper chest. We looked at my reflection in the mirror and I looked like a woman.

"One last thing," she said as she ran to the bathroom. As she returned she said, "For most women, the bare minimum of makeup is a touch of lipstick. I think a bright red would look good with your hair." She was like an angel in white lingerie as she faced me and applied the lipstick to me.

"There!" She turned me toward the mirror and I saw a woman in a dress next to one of the hottest teachers in silky white bra, panties and stockings. I felt something change in me. The panties, bra, dress and everything was overwhelmingly sexy. I wanted to be her girl, I wanted to look sexy for her, and, most of all, I wanted to return the pleasure.

She was proud of herself and looked at me with a new desire. "I think you like this game," she smiled. "Well, I like it too." She started walking towards me. "I like to teach, Hon, and you are very teachable." She took my hand in hers, "I also demand some attention from my students."

She had played dress up with me like I had fantasized for years. She had taught me to be open minded in class, and now she was teaching me to be my feminine self in her bedroom. I would have done anything for her in return.

"Come," she whispered, and pulled me toward her bed. "Keep your dress on for a bit, I want you to enjoy wearing it, and really, all I want right now is your mouth. Take my panties off and kiss me."

I knew what she wanted. She laid on the edge of her bed with her knees in the air and I pulled off her panties. My breasts pulled the front of the dress tight as I moved my arms up. Her pussy was beautiful -- a little patch of hair and the prettiest lips I've seen -- all framed by the garter belt and stockings. I may love wearing panties, but I love licking pussy more.

I went to work on her pussy. My kisses started lightly and I dove in deeper.

"Oh, god, Jackie, that feels fantastic," she said as I focused on her clit. "Getting you all dressed up was very sexy for me. Oh, I love having a girl like you licking me," she moaned as she ran her hands through my new long hair.

I kept devouring her pussy trying to tell myself this was really happening.

"Oh, Jackie, keep it up. Oooh, eat meeeee," she squealed.I lapped everywhere. From the bottom of her slit to her clit. From one thigh across to the other. I was in heaven with my mouth on my teacher's pussy. I could tell she was nearing ecstasy.

"Woo. Woo. Wooooo," she purred as she wrapped her legs around my head and pulled me to her while she orgasmed.

I continued to lick and kiss her while she calmed down, following her pussy juice to her ass. She pulled her legs up toward her chest to give me more access to her delicate hole and I lapped at the juices that collected there.

"Jackie, I think you messed up your lipstick, Hon," she said slowly, "and, I need a little break."

We relaxed for a bit and I had the chance to walk around in my dress a little more. She sat on the bed to watch me sashay around her bedroom. I really enjoyed being dressed like her and she was so warm and supportive.

"Jackie, you really are pretty and I can see that you are enjoying our time together. It makes me hot to see you like this."

"Thank you, Susan. It feels very sexy to me. It makes me feel close to you to wear your dress, and I hope you like my boobs," I said trying to hide my shyness. My voice was softer and just on the higher end of my normal talking voice.

She came over to me and embraced me. "I like them very much," she said as she started to unwrap the dress. "In fact, it's my time to play with you."

She kissed my neck, ears and lips as she positioned me to lay on the bed, the dress open on the front. She reached down to my panties and caressed my cock. "Oh, Jackie, I think you've enjoyed this quite a bit. Your panties are already wet."

Of course they were. I had been leaking cum since she took off her dress and put it on me. I was so, so turned on.

"Let me see what we can do with this beautiful cock before you squirt everything out," she said as she moved the panties to one side and pulled my cock out through a leg hole. She caressed my panties as if I were a girl and reached into my bra to pinch my nipple.

With me on my back, she straddled my cock and slowly slid it into her wet pussy. I moaned a soft squeak as we joined our bodies. She was in control and I loved it.

"Fuck me," I said softly. "Oh, Susan, fuck me please."

She moved sideways slightly so we were like two women in a scissors position. She ground her pussy against me while playing with my tits. My cock was embedded in her but the way she played with my nipples set me off. I was soon screaming like a woman, "oh, oh, oh. Yeah, yeah, fuck me."

Just when I thought I couldn't get any more pleasure, she pinched my nipple hard and pulled. I came like mad as our bodies rubbed together and I yelled, "oh, God, yesssss."

She lay on top of me and kissed my face. After a minute or two of silence and fatigue, she said, "Jackie, you are a beautiful lay."

I breathed, "Susan, this has been incredible. I can't wait to do more with you."

"Oh, Hon, just relax. The rest of the day is our girl time," she responded. "In fact, if all goes well, I'm going to teach you a few more things about being fucked like a woman."

I didn't know what she meant, but I knew I would be her willing student.