Thrift Store Encounter
She greeted me with a friendly smile and asked if there was anything she could help me with. I barely looked at her. Then, as usual, I blushed deeply and squeaked that I was just looking.
With my eyes on the floor directly in front of my feet, I headed straight for the women’s section. I thumbed through the shorts looking for a cute pair with no more than a two-inch inseam. I paused when I saw this adorable pair of high-waisted, white shorts that had no zipper, only three big buttons up one side.
From over my shoulder, I heard a feminine whisper, “You’ll look adorable in those.”
Turning around while biting my lower lip, I looked up into her eyes. I failed to notice how tall this woman was. She towered over me with nearly a full head. She had crept up behind me so quietly, and I had no clue she was anywhere close to where I stood. I whimpered and mumbled something about shopping for someone else. And I know I was blushing from head to toe!
She smiled warmly and gently touched the palm of her hand to my cheek. In a calm, soft voice, she told me I didn’t need to be nervous. She said she’d been watching me come into her store for weeks. She could tell how badly I’d wanted to look through the junior’s racks. And with just the two of us in her shop, I could look at whatever I wanted.
She reached out and took the hangar with the little white shorts off the rack. She peeked in at the label and then let her eyes drift up and down my body. Nodding her head, she agreed that I’d chosen the correct size.
Laying a finger under my chin, she lifted upward until our eyes met. She asked if I’d like to try them on. I wanted to so badly! But this was way beyond what I had planned to accomplish that day! In my mind, I was going to find a pair of shorts on the rack, pay for them and leave. But looking up into her eyes, it felt like my spine was turning to jelly. I bit my lower lip and told her I would like that very much. She laid her free hand on my lower back and guided me toward the ladies dressing rooms. I couldn’t stop shivering with excitement when she reached up and slid one of the curtains open for me. Stepping into the little room, I turned back and quickly thanked her for being so understanding. She smiled and told me it was no problem at all. While sliding the curtain closed, she told me she’d be right outside if I needed her opinion on the fit.
I stood there holding those little white shorts and waited to hear her walk away. She took, at most, 4 or 5 steps. I peeked out from behind the curtain and saw her standing by a rack of clothes, patiently waiting for me, her only customer. Closing the curtain, I slipped off my shoes and slid my pants down and off. I felt as if I were in a dream! I was changing my clothes in a lady’s dressing room! When I raised my foot to step into the shorts, she asked if I needed any help. I slipped my leg into the shorts and heard her approach my dressing room. When I bent over and raised my other foot, I peeked under the curtain and saw her shoes, which were almost close enough for me to reach out and touch!
Wiggling the shorts up my legs and over my hips, I closed the buttons and admired myself in the narrow mirror hanging on one wall of the dressing room. From the opposite side of the curtain, she asked if I’d like to look at myself in the bigger mirrors just outside of the dressing rooms. When I stuttered and stammered, she slowly opened the curtain and became the first person to see me wearing girls’ clothes. Goosebumps popped up all over my body, and I blushed deeper than ever before. There was no way I could look her in the eye on my own. It took her reaching out, laying a finger under my chin, and lifting upward until our eyes met. She was smiling warmly and looked directly into my eyes. I squirmed where I stood, and I was so embarrassed!
Lowering her arm, she took my hand in hers. She looked across the store and found no one was about to walk in. When she was satisfied, we were still alone, and she led me to a nearby bank of three mirrors. They were arranged so that the two end mirrors were sitting at an angle, allowing one to see more of themselves. She stepped behind me and had me hold my shirt up so we could see where the shorts ended well above my waist. She rested her hands on my hips while I stood directly in front of the mirrors.
Looking over my shoulder, sliding her hands up and down over my hips, she told me the shorts were a perfect fit. She went on to tell me I’d need to get myself a thong or go without panties while wearing them. They fit so snugly that she could see the lines of my underpants. I stood there silently listening to her. I’d never had anyone give me advice like that. No matter how embarrassed I was, I wanted to be sure I heard every word she said.
She had me turn to the side so I could see my butt in a mirror. With her index finger, she gently traced the line of my underpants across my cheek. She told me panty lines always needed to be avoided. Feeling her finger slide across my cheek expectedly affected me. My penis struggled to become erect.
She gently turned me back to face the mirrors. In that same understanding voice, she asked why I had tucked myself back between my legs. She stated that it must be painful in that position. I looked at her in the mirror and told her I thought that was what I was supposed to do with it. She spun me around, so we faced each other. With her hands still on my hips, she told me that I didn’t have to tuck. I could leave it right up front for everyone to see.
I must’ve looked confused because she went on to explain that she, like many other men and women, preferred to see a feminine boy’s bump. I shouldn’t try to pretend I was a girl. I needed to be proud that I was a gentle boy who preferred the softer and more delicate fabrics that girls wore. With a gentle pat on my bottom, she guided me back to the dressing room to try it out.
As soon as the curtain closed, I undid the buttons on the shorts, reached down, and repositioned my penis up front where it normally resided. I’d barely gotten the buttons reclosed when she threw open the curtain again. In the same manner, as before, she guided me to the mirrors and stood behind me. I held my shirt up high enough that a strip of my pale skin could be seen between the waist of the shorts and my shirt. She was looking over my shoulder, standing close enough that I could smell her musky perfume. Stretching her thumbs across my hips, her fingers were resting dangerously close to the lump that was my very erect penis. She whispered, “Yes, that’s much better.”
She began talking while her fingers and thumbs massaged my hips. She explained that when I left my penis upfront, anyone who saw me would immediately know that I was a special young man who wasn’t ashamed to dress stylishly. We were both watching my penis throb under the thin material of my underpants and the shorts.
At some point, she turned me to the side so I could see my butt again. Neither of us spoke as we looked at my body from the side. The cut of the shorts seemed to nip in at my waist, emphasizing my hips. My legs looked longer than usual. Still holding my shirt with both hands, I lifted it even higher, exposing more of my pale stomach and chest. I’d never felt so pretty.
Reaching down, she gently dragged her first two fingers along the exposed flesh of my left cheek that was peeking out from under the shorts. In a grave whisper, she said, “With your tight, little figure, you could wear so many cute outfits.”
While still behind me, she turned me back to face the mirror. Bending down, she reached between my thighs near my knees and slowly drug her hands upward. I whimpered softly, and my hips began to grind back toward her. When standing up straight with her hands on my hips again, she whispered, “Sooner or later, you’re going to have to address the hair on your body. It is light blonde and sparse, but it should really be removed. Your body needs to be perfectly smooth and soft when wearing cute little clothes like these shorts.”
Between the sensation of feeling her warm breath on my neck, the scent of her perfume filling my nose, and her gentle touch on my body, I was ready to squirt where I stood. We both looked at my reflection in the mirror. Her hands slid up and down across my hips.
In that same soft whisper, she said, “When you’re ready to have this hair removed, just let me know. My niece owns a body waxing salon not far from here. She often complains that her clientele is lacking gentle, feminine boys.”
Her hands slid forward and framed my very erect penis under the thin cotton shorts. She was careful not to let her hands make contact with the throbbing bump under my shorts. I moaned softly and pressed my hips back against her. Her lips brushed against my ear while she told me that body hair was for big, strong, masculine men. A sweet boy such as myself should be kept as smooth as a baby’s bottom.
Her hands moved closer to my throbbing erection. She brushed her lips against my ear again when she told me that long, fat cocks deserved to have pubic hair. She licked my ear before whispering, “Little, pink penises should never be kept hidden beneath hair.”
By now, I was so aroused I was ready to squirt with the slightest amount of friction. We both looked at my reflection in the mirror. Her hands slid away from my penis and to my hips. They then moved up to my waist and continued until I felt her warm touch on my bare skin. I bit my lower lip and lifted my shirt even higher, just above my collarbones. She smiled behind me, and her hands drifted up until her fingers were able to gently pinch my pink nipples. I whimpered softly and ground my hips back against her.
After glancing over her shoulder, she returned her attention to me. In that same gravely whisper, she said, “You are still my only customer.” She laid her hands on mine and gently helped me pull my shirt up and off of my body. I stood there, looking at my reflection, wearing only the little shorts and my underpants. She tossed my shirt over the back of a nearby chair. When she returned her gaze to the mirrors, I felt more naked and exposed than I ever had before.
She moved in close behind me again, close enough that I could feel her clothes against my naked skin. Her hands slipped around my hips and slid up to my waist. Her eyes zeroed in on mine when she reached for the first big button on my shorts. I squirmed and pushed my hips back against hers.
In a squeaky voice, “Someone could walk in! They would see me in my underpants!”
She whispered right into my ear, “No, they wouldn’t. If someone walked in here in a few moments, they would see you naked. Because your underpants are coming off too.”
I whimpered softly, and my hips pressed back against her. She popped open the first button, then the second, and finally the third. I squirmed under her touch. She spread the flaps of the shorts open wide. I could hear and feel her breathing on my shoulder. I whimpered softly, “Please.”
She grinned and answered, “Please what?”
I bit my lower lip. I looked at her reflection in the mirror and moaned, “Please don’t do this. Not here.”
She smiled, “Yes, Sweetheart, right here, right now.” And she slowly began to lower the shorts I wore. I stood there and let her do it. I don’t know why I didn’t stop her. I stared at myself in the mirror. I had my arms lifted up out of the way. My penis was rigid and poking against my underpants. There was a moist spot growing slowly near the head. My hips were squirming from side to side, and soft moans were slipping through my lips. When the shorts fell around my ankles, she had me step out of them one foot at a time.
She tossed the shorts over the back of the chair, joining my shirt. While still squatting behind me, she hooked her thumbs into the sides of my underpants. She looked up at my eyes in the mirror and began to lower my underpants. She moved painfully slowly. When she pulled the front forward to allow my stiff penis to escape, I pushed my hips back toward her. Once the pink head of my penis appeared, she grinned and lowered my underpants the rest of the way. As before, I stepped out of them one foot at a time. And then my underpants joined the other clothes I’d been wearing over the back of that chair.
Standing naked in front of a bank of mirrors in the rear of a thrift store was an incredibly nasty feeling. I’d just been stripped by a lady old enough to by my mother. And I wasn’t even trying to cover myself up. I was breathing in heavy gasps. My penis was throbbing, and drops of my excitement were forming under its squishy pink head.
After rising up behind me, she leaned in close and whispered in my ear, “Stay right here. Do not move. Do not get dressed. Do not touch yourself. I’ll be right back.”
She then turned and made her way through the labyrinth of clothing racks toward the front of the store. She first flipped the ‘open’ sign to ‘closed’ and then turned the lock on the door. While she did that, I glanced over and saw the clothes I’d been wearing over the back of that chair. Further away, I saw my pants, shoes, and socks inside the dressing room I’d used.
I could have quickly gotten dressed and ran away. I could have left that store and never returned. But I didn’t. I chose not to. This woman knew who I really was. She knew what I wanted and needed. In the short time I’d spent with her, she had learned more about me than anyone else I’d ever known. I had no intention of leaving. I wanted to find out where this woman would take me. I needed to spend as much time as I could with her. I felt my heart well up in my chest when I silently made these decisions.
Standing there naked with a full erection that was dripping on the floor, I watched as she turned from the door and walked back in my direction. She was looking at me, and I was looking at her. My heart began beating heavier and heavier the closer she got. I squirmed where I stood, but my feet never moved.
When she stepped around the last rack of clothes separating us, she walked right past me. She picked up the clothes I’d been wearing from the back of that chair and continued on to the dressing room where I’d changed. After picking up every other piece of clothing I’d worn that day, she turned back around and moved behind me. She leaned in close enough that I could feel her lips brushing against my neck when she spoke, “Such a good boy, doing exactly as you’re told. Wait here for just a little longer.” She then gently kissed my neck, just below my ear.
With all of my clothes, she went back to the front of the store. I couldn’t see what she was doing, but when she returned several minutes later, my clothes were nowhere in sight. I whimpered softly but didn’t ask what she’d done with them. At that moment, I didn’t care.
She stood right behind me, rested her hands on my naked hips, and pulled my butt back against her. She ground her hips against my bare behind. We looked at each other in the mirror, and with her lips brushing against my ear, her hands drifted up and down my naked sides.
In a soft whisper, she said, “My first marriage ended when I caught my husband cheating with a girl half my age. I was not going to allow that to happen again. So, my second husband, I stripped him naked, took him on my lap, and masturbated him three times a day, every day throughout our 15 years together. He passed away suddenly four years ago. And until you walked into my store, I didn’t think I’d ever find someone like him again.”
“My late second husband was much like you. He was quite a bit younger than me at the time. He was small and petite with a cute little figure. I used to love taking him out dressed in panties, dresses, skirts, or tiny shorts. We once went on a vacation to the Caribbean and the only swimwear I packed for him was a girl’s one-piece suit. He loved it almost as much as I did. And looking at you right now, I know you’re just as sweet and submissive as he was.”
She pulled me back against her hips hard and ground my bottom against her. In a raspy whisper, she asked, “What is your name, Sweetheart?”
My voice cracked when I answered, “Sam, Sammy.”
She grinned and asked, “Is that Sami with an ‘I’?”
I whimpered softly and felt my hips buck against her grasp on my hips. Before I could answer, she asked, “How old are you, Precious?”
Biting my lip, I glanced into her eyes in the mirror and squeaked, “23”.
She smiled, kissed my neck, and whispered, “I was almost thirty when you were born.”
I moaned and unintentionally ground my bare butt against her hips. With her hands still on my hips, she pulled me against her hard. “My name is Lisa.”[table “41” not found /]
Her hand slowly slid around my front until her fingers and thumbs framed my extremely stiff penis. She licked my earlobe and whispered, “Sweet Sami, has anyone ever touched your little penis before?”
I rose up on my tiptoes and pushed my hips back against her. My penis was small, and I knew that. I’d seen other guys in the showers and knew I was absolutely tiny compared to some of them. But no one had ever told me I was small before. Having this grown woman tell me what I’d always known deep down inside was both humiliating and also wildly arousing. She was honest. I was thrilled to be standing there with her. Answering her question, I whimpered softly, “No. Never.”
Leaning in close, she nibbled on my earlobe before saying, “Well, this is your lucky day. Sami, I’m going to touch you now. I’m going to stroke your little-bitty penis up and down until you squirt for me.”
Her large hands moved toward my aching penis. She moved so slowly. I was going crazy with desire. I wanted her to touch me so desperately. When her fingers drug through my pubic hair and then finally looped around the stiff prong of my penis, my hips bucked forward, and a pearly drop of my excitement formed on the squishy pink head of my penis.
She groaned in my ear, “Your penis is so tiny. It is the smallest, most delicate one I’ve ever seen. Don’t worry, Sweet Sami, and I won’t break it. I’ll be gentle with you.”
She used her first finger and thumb to slowly slide up and down along its length. I whimpered and moaned while she continued to tease my penis and whisper in my ear. “A darling little penis like this should be kept in panties, don’t you agree? And a boy with such a cute figure shouldn’t wear baggy clothes. No, a boy as cute as you should wear dresses, skirts or tight little shorts. Yes, girly clothes for a girly boy.”
Every time I got close to squirting, she would take her fingers away from me until I’d calmed down. When that dangerous level of arousal had passed, she would begin playing with me again. After the third or fourth time, she licked my neck and whispered, “Are you a sissy Sami?”
Bucking my hips back into her, I groaned, “Yes.”
“Sweet Sissy Sami, would you like to be kept in cute girls’ clothes all the time?” She continued to tease my rigid penis with her fingertips. We both watched drop after drop of my excitement fall to the floor near my feet.
I squeaked, “Yes!”
“Sissy Sami, you’d never, ever wear anything remotely masculine ever again. You’d spend the rest of your life in adorable girly clothes or nothing at all. Is that what you dream about? Is that what you really want, Precious?” She leaned in and kissed the side of my neck, which sent chills throughout my body. And at that same moment, I got closer to squirting than any other time since we started. Lisa removed her touch and waited patiently for me to calm down.
When my breathing had slowed, and I was no longer in danger of squirting, she resumed teasing me with a feathery touch. And she continued whispering in my ear, “Sweet Sami if you only wore dresses, skirts, or tight little short-shorts, what would your friends think? What would your co-workers and boss think?”
In a high pitch, I squeaked, “I don’t care.”
She continued to stare at my bare body in the mirror while leaning in to lick my earlobe. “Good boy. You could always get another job or different friends. But what about your family? What would your mother and father think when you started prancing around in girly clothes all the time?”
She kept teasing my aching penis with her fingertips while I tried to answer her question. But it was difficult to concentrate, and she kept pulling my hips back against her. I somehow managed to tell her that I thought my father already knew I was a sissy. I told her I didn’t think he would be surprised at all, nor did I think he was upset that his son was a sissy. Lisa kept teasing my inexperienced body and told me I was lucky to have such an understanding father. She then asked about my mother.
I squirmed under her touch and explained how my mother had left when I was young. But my father had been living with a woman for several years.
Lisa asked how I thought she would react when I started wearing sexy little outfits all the time. I moaned deeply and spun around while looping my arms up around her neck. I asked her if we could please stop talking. She told me she wanted an answer about my father’s girlfriend, how would she react. She then turned me back, so I was facing the mirror.
I watched her fingers teasing my throbbing penis while whispering, “I think she would like it.”
That answer piqued her interest, and she began quizzing me about my relationship with her. I told her we had a very good relationship. She was very nice, and I liked her very much. I bashfully admitted that she had once caught me playing with myself and somehow didn’t make it super uncomfortable.
Lisa stopped me asked, “Sweet Sissy Sami, do you still live at home with your dad and his girlfriend?”
When I told her I did, she licked my earlobe again and told me that it was absolutely perfect. She urged me on to tell her more about Julie, my father’s girlfriend. She asked what she looked like. All the while teasing my little penis and occasionally pinching my nipples.
I explained that she was tall, had big boobs, wide hips, and always wore dresses or skirts. I’d never once seen her wearing pants. She had pretty blonde hair, big blue eyes, and always seemed to be happy. She is the nicest woman I’d ever met.
She removed her fingertips from my body and let me stand there, tingling all over. In a soft whisper, “Do you think Julie would enjoy taking you shopping for cute girly outfits?”
I half moaned, “I hope she would.”
She smiled while letting her fingertips drift over my body and once again tease my penis and nipples. “Sweetie, I don’t know what you’ve been waiting for. Your dad already knows you’re a sissy. And his girlfriend has seen you playing with your little penis. She obviously thinks you’re just as cute as I do. You should already be running around in girly clothes.”
I squirmed under her touch and glanced down at the small pool of my precum that had formed on the floor. I whispered, “I don’t know. I guess I’m just afraid.”
She kissed my neck and held me against her soft, warm body. “Sweet, sweet, Sissy Sami, I want you to come back and see me at this same time next week. Okay?”
I ground my bottom back against her and moaned, “Okay.”
Lisa loosely looped her fingers around my penis and let me hump myself in and out of the ring she had formed. She whispered, “But Sweetie, I don’t want you to come back here unless you have a little talk with Julie. I want you to tell her you to need new underpants. But I also want you to ask her if she thought it would be weird if you wore panties instead of boy’s underpants. Do you think you can do that for me?”
She had been controlling my level of excitement by loosening and tightening the ring my penis was sliding through. I moaned that I could. I babbled on about my dad being out of town on business for the next week. Which meant I’d have plenty of opportunities to talk to Julie.
Lisa smiled behind me. While I humped my penis, she tightened the ring her fingers had formed. She whispered, “One last thing. Whenever your father isn’t home. I want you to leave your bathroom door wide open when you shower. It will be good to know if Julie takes that as an invitation to come to watch you.”
I squealed that I would. I promised Lisa I would do all those things. And after all that time, she finally continued to stroke me and allowed me to squirt. I reached back and laid my hands on her thighs as I fell back against her. My body went into convulsions as my little penis spurted out globs of my creamy juices onto the floor of her thrift shop. Strange, high-pitched squeaky noises escaped my lips with each stroke of her hand.
As the most powerful orgasm of my life came to an end, Lisa wrapped her arms around my body and pulled me against her. We looked at ourselves in the mirror and watched my penis slowly soften. I felt her warm breath on my ear and neck. Her big boobs were pressed against my naked back. My legs were wobbly, but Lisa held me safely in her arms.
In a soft whisper, she said, “If you come and see me next week and promise you’ve had the talk with Julie and left your bathroom door open while you showered, I promise I’ll drive you to my niece’s salon and cover the cost of getting your body waxed. I’ll even be in the room while she does her magic. I’ll hold your hands while she waxes you. And after she’s finished and you’re nice and smooth, I’ll take your little penis in my hand and make you squirt while she stands nearby and watches.”
She continued to hold me in her arms and said, “Please don’t disappoint me. And don’t try to lie to me either. Sweet Sissy Sami, you wouldn’t be the first young man I had to discipline over my lap.”
I moaned again. The idea of laying across Lisa’s lap while spanking my naked bottom sent shivers up my spine. She must’ve known what I was thinking because she went on to say, “Sissy boys are all the same. I mention a spanking, and you immediately think it would be a naughty spanking. That is not what I meant at all. A discipline spanking isn’t meant to be pleasurable. It is meant to hurt. It will remind you that you made a mistake that shouldn’t be repeated. Do you understand me?”
After telling her I understood, she firmly took my hand and began walking toward the front of her store. I pulled against her, with every step we took, we got closer to the big glass windows. Anyone outside would be able to see me! I squealed and begged her to stop, but she just kept walking. As my naked body cleared the last rack of clothes, I moved right behind Lisa and hid.
When we stood at the cash register, Lisa turned to face me. She asked me what Julie would think if I arrived home naked. I shivered at the thought. She smiled and suggested sending me home in the little shorts I’d tried on earlier, along with a cute top and some flats. I whispered, “Please not yet.”
A wide grin spread across her face, it reminded me of the Grinch in that movie. She leaned in close, so close her lips brushed against mine when she spoke, “Yet, you said, ‘Please not yet.’ That is very interesting. Unless you want me to send you home to Julie dressed like the sissy you are, you’ll walk to the front door, flip the sign to ‘open’ and unlock that door. Go. Now.”
I peeked around her wide-body and judged the door to be more than a dozen steps away. And there was nothing for me to hide behind at all. There weren’t a lot of people on the sidewalk in front of the store, but occasionally a few people would pass by. As if reading my mind, she whispered, “You’ll need to walk, not run. And don’t even think about covering up.”
Just before I moved out from behind Lisa, she reached down and took my surprisingly stiff penis between her first finger and thumb. She squeezed it and said, “If you’re this excited now, wait until Julie sees your bathroom door wide open while you shower. Sweet Sissy Sami, she is going to love it, and so will your little penis!”
My heart was pounding in my chest as I stepped out from behind Lisa. I took measured steps toward the door. Just before I’d reached for the sign, three cars drove by, one after another. A shiver of shame ran through my body. None of the cars stopped or even slowed down. I doubted anyone saw me, but they could have. I quickly flipped the sign and turned to the lock. As I spun around on my toes, I heard another car drive by. And just after I’d gotten behind Lisa once again, I heard two ladies talking and watched them walk past on the sidewalk in front of her store.
She leaned down and kissed my cheek while whispering, “You really are a good boy. A promise is a promise. Here you go.” And she handed me my neatly folded clothes with my shoes on top. I glanced around the store nervously for a few moments, then timidly asked, “May I go get dressed now?”
She smiled at me and gave me her permission. I quickly turned and raced off toward the ladies dressing rooms. When I’d entered the little room and closed the curtain, I leaned against the wall and tried to process all that had happened since I’d walked into that store. The promises I’d made regarding Julie, my father’s girlfriend, stood out the most. My mind was telling me not to go through with those promises, but the rest of my body cheered me on to complete the tasks I’d promised to do.
When I had my clothes back on, I pulled open the curtain and stepping into the store. Lisa was standing at the register talking to a customer who had just entered her shop. I waited patiently for her to finish the conversation before approaching her. She set two bags on the counter, leaned close, and whispered to me. “Those cute shorts you liked so much are in here along with a few other things you might want to start wearing around the house. These are my gift to you.”
She glanced around the store and saw the lady who had entered was occupied. Lisa then kissed me gently on the lips. “Sweet, Sissy Sami, I hope you do all those things you promised. And I really hope you come back and see me next week. I hadn’t had this much fun since before my second husband passed away.”
I promised I would live up to my promises and then picked the bags, and I made it all the way to the door before I stopped. I turned and quickly walked back to Lisa. I set the bags on the counter and whispered, “I don’t want to leave yet.”
Lisa smiled brightly, she told me I’d just made a fantastic day even better, and of course, I could stay. She then told me to go choose one of the ladies dressing rooms and remove my clothes again. She told me she would stop by in a few minutes to take them all from me. She said as soon as we were alone, if we were alone before closing time, she would come to get me. I would wander the racks naked and choose girly things my heart desired. We’d go on a sissy shopping spree.