Dental Assistant

For as long as I can remember, my dentist had the same assistant. Tina was an older woman, very busty, rather plump, and always friendly woman. Over the years, we'd gotten to know each other rather well during my routine cleanings. She always asked about my girlfriend Sara and the things I'd been up too. I learned early on that she preferred not to talk about her personal life. She was widowed and her grown children visited so rarely, she hadn't met several of her grandchildren.

During my most recent dental appointment, while climbing into the chair and having a bib wrapped around my neck, Tina asked about my girlfriend. I bit my lower lip, looked up into her big brown eyes, and told her that we'd broken up almost 3 months ago. She laid a hand on my chest and told me how sorry she was to hear that. I told her it was okay, that I was slowly getting used to being alone.

She left her large, warm hand on my chest and consoled me for a short while longer before telling me we should get started with my cleaning. While I laid on the chair with my mouth open wide, Tina began to carefully scrape away the plaque which had accumulated since my last visit.

While she worked, she asked, "Now that I know you broke up with Sara, it explains why you haven't posted any new images or videos."

My eyes opened wide and couldn't believe what she had said. But I couldn't respond until she stopped working in my mouth. I know I was blushing when I asked, "What do you mean?"

She went back to work and I had to open my mouth wide which kept me from responding. She was leaning over me more than usual and one of her breasts was touching my shoulder. In her normal tone of voice, she said, "' Precious Pat' is the name you use. And I've been a fan of yours for a very long time."

I squirmed in the seat and felt my skinny, little penis begin to grow in my panties. When she removed her hands and let me swallow, I softly said, "Really? I mean, you're the first person I've ever met that has seen those pictures and videos. I'm so embarrassed!"

She went right back to work in my mouth and said, "Embarrassed? No. You should be flattered. I may be your biggest fan. I have even bought a few things for you off of your wish list."

I tried to feel flattered, but knowing the pictures and videos Tina may have seen wouldn't let me feel anything other than shame. I knew this could happen. Sara and I had long talks about how I'd feel if I ever encountered someone who recognized me from my website. Sara knew how embarrassed I'd be and often teased me while in public about all the strangers having seen my most recent posts. Those times didn't compare to the feelings burning in my stomach, they were even worse than I imagined them to be.

But I was stuck, I couldn't get up and run out. When Tina paused to rinse my mouth and suck out the water with the sucker-tube thing, I swallowed my shame and asked, "Did you really buy things from my wish list?"

She smiled warmly and said, "Yes, a few things. I remember buying the days-of-the-week panties around the holidays. And most recently I bought a cute, little plaid dress and matching bloomers."

My penis became completely erect and throbbed after hearing those words. My back arched and I whispered, "I wear those panties all the time."

After returning to work, she said, "That is just adorable. I often watch that video of you modeling those panties that you posted."

I squirmed in the dental chair as I recalled the video Sara shot of me modeling one pair after another. Recalling what I did at the end of that video made me feel ill. Tina had watched me slide a dildo in and out of my behind! Even more, she had watched me tickle my little penis with a single finger until my creamy love burst out onto my stomach. I was so ashamed!

While still cleaning my teeth, "Sweetie, I told you before, you do not need to be embarrassed. I am your biggest fan." She paused to change tools, "And you should know, every time I see you on the schedule, I fantasize about you arriving in a little dress."

A soft moan slipped through my lips and after swallowing, I whimpered softly, "I'm sorry I disappointed you." I was sorry I'd disappointed her. I'd always been the sort of boy to strives to please women. In a whisper, I offered, "But I am wearing my Friday panties."

Glancing out the archway, I quickly reached down and pulled my denim shorts away from my belly so she could see that I was telling the truth. In the process, I know she got a peek at the little lump my erection was making beneath the thin cotton of the panty.

She pressed her giant boob against the side of my face briefly and whispered, "You are so cute. But I really would have preferred you to show up in the little plaid dress and bloomers I bought for you. You know, I still haven't seen pictures or a video of you mincing about in them."

My little penis was throbbing wildly and I reached down and squeezed it before I realized what I'd done. Tina smiled, leaned close to my ear, and whispered, "Don't worry, I'm quite horny too."

Before she began to brush my teeth, I quickly admitted, "Sara and I planned to take a video of me wearing that dress and walking through City Park early in the morning." I blushed and forced myself to continue, "The video was going to end with me laying on a picnic table."

She whispered, "And what would you have done on that picnic table?"

Glancing out toward the hall first, I then whispered just as quietly as she did, "I would have touched myself until I squirted."

Her warm breath caressed my neck and she pressed her big breast against my shoulder a little harder. "I would have loved to watch that one. But it never happened. Is that because you broke up with Sara?"

I nodded my head just enough to let her know my answer, while not interrupting her brushing.

She whispered, "Sweetheart, I think I deserve to see you in the little dress I bought. In the past, you always posted pictures or a video showing you in the gifts your admirers bought for you. I feel cheated."

When she finished brushing my teeth, she rinsed them with water and sucked it out with a tube. I was so embarrassed and turned on at the same time, I couldn't even speak. I laid there passively while she pulled off a long string of dental floss. After winding it up on her fingers, she stuck them in my mouth and began to give me a very thorough flossing.

She glanced at the archway before leaning down and whispering, "Pat, do you have plans tonight?"

Looking up into her warm, brown eyes, I shook my head just a little bit from side-to-side.

She frowned, "That's a shame. You're too cute not to have plans on a Friday night." She focused on flossing my teeth for a little while before glancing to ensure we were still alone. She then stopped flossing and let one of her glove-covered fingers slide along my tongue in a very inappropriate manner. Her index finger slid in and out of my mouth on top of my tongue. While staring into my mouth, she whispered, "Why don't you come to my home tonight. It will allow you to model that little dress for me. And there is a home-cooked meal in it for you too. I have a stew in the crockpot." She continued to tease my tongue with her finger and gaze into my mouth for a few moments before returning to the task of flossing my teeth.

When she'd finished flossing and before she'd rinsed my mouth, I whispered, "Really? You want me to go to your home for dinner?"

She began to rinse my teeth again and sucking out the excess water. She intentionally let that vacuum tube attach itself to the tip of my tongue several times. I was a horny little mess! It was too noisy to talk over, so I waited until she was done before whispering, "Like a date?"

She smiled down at me, "I suppose it will be like a date. What do you think? Do you want to join me for dinner?"

I smiled and spoke louder than I'd planned to, "Yes, I would like that very much."

For all my previous visits, Tine knew I preferred the bubblegum-flavored toothpaste and had it already prepared. She dabbed the rotating toothbrush in the paste and went right to work. After polishing the outside of my lower teeth, she rinsed them and sucked out the excess water. Before she went back to work, she paused and slowly slid two of her fingers in and out of my mouth. She didn't say anything at all. I soon closed my lips around her fingers and swallowed. She gazed into my eyes and whispered, "You are so cute." After finishing the inside of my lower teeth. She again slid her fingers in and out of my mouth until I closed my lips and swallowed. Tina repeated that same routine for my upper teeth as well. By the time she'd finished, I was writhing in the chair!

Tina rolled her stool to a nearby counter and pulled out one of her boss's business cards from the top drawer. On its back, she wrote down her address and phone number in perfect loopy cursive handwriting. After rolling back to my side, she showed me what she'd written before taking the liberty of pushing it into the pocket of my shorts herself. In a sexier than normal whisper, "Dinner will be served at seven o'clock sharp."

My hips pushed up against her touch when her fingers entered my pocket. I breathlessly whispered back, "I won't be late."

When my dentist entered the room, I was so nervous! My penis was very stiff in my panties and I had this fear of him knowing what Tina and I had talked about. But I was worrying for nothing. The remainder of my appointment went by without further excitement. My teeth were in great shape and my next appointment would be in 6 months.

When my dentist left Tina and me alone again, she quickly prepared a bag with toothpaste, a new, pink toothbrush, and a small, pink container of floss. Before straightening my chair from its reclined position, she pressed her huge, soft breast against the side of my face and whispered, "Remember, seven o'clock."

My back arched and I whimpered softly, "I won't forget."

After making my next appointment at the front desk, I raced home to prepare for my date! I had less than three hours before I was due to arrive at her door. I took a long, hot, bubble bath before making my way to my dresser. While I was in the tub, I'd decided to wear the dress Tina had bought me for dinner. I'd originally thought about carrying it with me and changing at her house. But that seemed silly.

My stomach was quivering as I slipped on a white cotton, bikini panty. I'd decided not to wear a 'days of the week' panty, I'd been wearing my Friday panties all day. And wearing any other day was simply wrong. I next wiggled into the tartan plaid bloomers. The bloomers made my butt look huge! They were very poofy! The elastic at the leg and waist openings cinched in snuggly and then ruffled out a little bit. From the top drawer of my dresser, I chose a cute pair of white ankle socks with a ruffle around the top. I was thankful I'd treated myself to a mani/pedi the evening before at a local nail salon. After carefully slipping my feet into the pristine socks, I tiptoed to my closet and picked up my shiny black, mary-janes with their large silver buckles.

I sat down on the floor of my closet and slipped my feet into the shoes and closed the buckles, being careful to fold my socks down so the frill at the top flared out nicely. Rising back up, I looked at the mirror hanging on the door of my walk-in closet and thought I looked very cute. Moving to the far end of the closet, I fingered my way through my dresses until I found the tartan plaid dress Tina had bought for me. I raised it over my head and let my arms glide through the short sleeves while the dress fell over my body. Reaching back awkwardly, I pulled the zipper up which closed the bodice around my stomach and chest.

Turning to look at myself in the mirror, I was thrilled with what I saw. The cap sleeves of the dress gave way to a modestly scooped neckline. The bodice of the dress hugged my upper body and just below my belly button, gave way to a dangerously short pleated skirt. It barely kept my bloomers covered. And if I turned, even slowly, the skirt flipped out. The snow, white socks, and shiny black shoes topped off the outfit perfectly. But something was missing. Racing to the bathroom, I found the missing piece of my outfit. A matching, tartan plaid hairband. Sliding it from my forehead back, it gave my hair a decidedly feminine, but juvenile look.

After coating my lips with cherry Chapstick, I made my way back to my front door. I grabbed my driver's license, key-fob, phone, and card with Tina's address. I paused to take a deep breath before opening my door and making the short walk to my parking space in front of my duplex. My usually, nosey neighbor was thankfully, nowhere to be found. As I strolled toward my car, my dress flipped up with every step I took flashing the world the tartan bloomer covering my most private places.

I'd been in public in girl's clothes before, but it had always been with Sara. Fears of being found out sat heavily in my stomach. Every time I caught someone looking at me, my penis throbbed and I ground my bottom against the driver's seat. At times, during that short drive, it felt like there was a spotlight shining down on me attracting everyone's attention from miles around.

The drive to Tina's house didn't take long at all, even while sticking to surface streets. Her house was situated in a nice, upper-middle-class neighborhood. It was a huge, white with yellow trim, two-story home with a three-car garage. The front yard was well-manicured, as was every other home on her block. I slowly pulled to a stop in her driveway. I was immediately worried my junky little car looked terribly out of place in front of her home.

I sat there for several seconds while mustering my courage. I was about to knock on the door of a woman I'd known for several years. The same woman who had spent time watching the movies and pictures of me doing such nasty things! And more than that, she had paid for the dress and bloomers I now wore. My stomach was doing somersaults! But I eventually reached out and opened my door. I left everything in my car, my phone, license, key-fob, and Tina's address. My car had a keypad on the outside of the door which, for the first time, was going to come in handy.

When I stood up out of my car, I adjusted my dress to ensure it was still covering my bloomers. I then made my way to Tina's front door. I tapped on it timidly and waited nervously. If she hadn't answered when she did, I probably would have thrown up! But she did answer. And when her door opened wide, her eyes lit up and her plump lips formed a huge smile.

She left me standing outside of her door while exclaiming, "Pat, you look adorable!" Until that moment, I'd only seen her in dental assistant scrubs. That night she was wearing a modest, short-sleeved summer dress with large buttons up the front. The dress tried to distract from her enormous breasts but failed to do so. Her wide hips left the skirt of the dress hanging away from her plump shins. Stepping outside, she embraced me for the first time. Her big, warm arms pulled me against her soft, perfumed body and held me there. I tried to wrap my arms around her, but she was too big and my arms were too short.

When the hug came to an end, she stepped back, took my hand, and welcomed me into her home. We stood there in the entryway of her home and while still holding my hands, turned to face me, "I didn't expect you to arrive wearing the dress. But I'm really glad you did." She released one of my hands and raised the other above my head. I blushed while turning around like a ballerina before her.

I giggled, "I'm glad you like it!"

She let go of both my hands while reaching down to take hold of the hem of my dress. Without warning, she lifted it completely exposing my bloomers! I squirmed and blushed like crazy.

Her eyes wandered from my shiny mary-janes to my bloomers and on up to my blushing face. "Oh yes, the bloomers do make this outfit."

I squeaked while squirming my hips back away from her, "Yes! I think so too!"

Releasing my dress, she slipped her hands underneath it and rested her warm, open palms on my bloomer-covered hips. Looking down into my eyes, she asked, "Patricia, are you wearing anything under these bloomers?"

I bit my lower lip and tasted my Chapstick. My voice was squeaky and high pitched when I said, "Yes."

She hooked her thumbs under the elastic waistband of the bloomers and asked, "Are they your Friday panties?"

I'd been in her home for less than a minute and she already had her hands under my dress! My little penis was stiff and throbbing under the thin cotton of my panties. Thankfully, my bloomers were poofy enough to keep my little erection well hidden. I whimpered softly, "No, I'm sorry. They were dirty. I have a different, clean pair of panties on now."

While pulling the sides of my bloomers out, away from my hips, she said, "Plain panties? We'll have to see about that."

Finding myself hornier than I had been in a very long time, I needed to change the subject of my panties to something else or I was in danger of squirting right there. I raised my chin a little and in a soft voice, "You look very pretty, Tina."

She grinned while removing her hands from under my dress. Stepping back, she looked down at herself before looking back at me. "Thank you, Patricia." She paused before asking, "You don't mind if I call you, Patricia, do you?"

I giggled and my hips swayed from side to side as I squeaked, "No, I don't mind. I like it. I like it a lot."

Taking my hand in hers, she announced, "Dinner isn't going to be ready for 30 minutes. Would you like a quick tour?"

Bouncing on my toes, I squeaked, "Yes! I'd like that very much."

She first led me down a flight of stairs. There was a large family room equipped with a comfy looking couch, chairs, tables, and huge television. Off of that room were the two bedrooms which once belonged to her sons. She hadn't changed anything in them. They were still decorated with posters of sporting teams, bands, and sexy girls. The rooms were neat, tidy, and appeared to have been recently cleaned. The other two rooms were the laundry room and bathroom.

She spoke in a somber tone, "I only ever come down here when I'm cleaning or doing laundry. My sons used to spend all their time down here. At one point in time, there was a constant flow of people and activities in this home."

Biting my lower lip and looking up into her warm brown eyes, I asked, "How long ago did your sons move away?"

She tried to look happy when she said, "Oh, it's been years." She counted them in her head before saying, "More than 15 years."

I stepped close enough to her that our bodies touched, "They don't visit very often, do they?"

She took me back in her arms and hugged me again while saying, "No, they don't. They have young families of their own and busy careers."

I leaned against her, resting my head halfway on her breast and shoulder. In the softest of whispers, I said, "I'm sorry, Tina."

She held me for a few moments before stepped back, taking my hand, and saying, "That's enough of that! I don't want to be sad while you're with me." She led me up two flights of stairs and it was obvious to me that she spent most of her time on this floor. It was tastefully decorated in the style of a middle-aged woman. The living room had stylish couches and chairs. There was no television, but I counted three different books laying on tables that she was in the process of reading. The lamps and tables looked old and expensive. It was a very nice, comfortable, sitting room.

The smell of dinner was strong and made my mouth water as we entered the kitchen. It was very large and well organized. There wasn't a formal dining room, only a table and chairs sitting opposite a counter from the kitchen. She checked on our dinner before returning to my side and taking my hand again. She led me back through the living room to what had been her daughter's room. Just like her son's rooms, it was left unchanged from the time her daughter left. It was a soft pink color with a full-sized white canopy bed. The dresser, nightstand, and vanity were all white with pink highlights. The walls were decorated with photographs of faraway cities, cheerleaders, and what had been popular bands at the time of her departure.