The Playful Babysitter Page 6

  “Honey, do you like these?”

  Kristen’s voice startled me out of my reverie. She held a delicate pair of lacy, sea foam panties in front of my eyes, stretching the waistband with two fingers.

  My voice caught in my throat. On the second try I managed to get out, “They’re pretty.”

  She winked. “I thought you’d like them. But I’m not sure if they’ll fit…these are a Medium.” With that, she lowered the garment in front of my waist. I blanched.

  Maybe I shouldn’t have been so forthcoming with my new girlfriend, I thought now. Going to Victoria’s Secret and browsing feminine underthings had always been a favorite pastime, and a solitary one. I enjoyed everything about it…the smells, the bursts of color, and the invariably attractive salesgirls, always ready to help – especially a befuddled male customer.

  While I’d experimented wearing panties, pantyhose and garter belts in the privacy of my bedroom, or on occasion venturing out with them under my male clothes, I’d always preferred the thrill of furtively selecting the items more than actually putting them on. Of course, I’d always pretend the underwear was for a special someone other than myself.

  This had always been an intensely personal pursuit. I’d browse for awhile, flirt with the salesgirls, and buy the garment…then go back to my apartment, put the item on and bring myself to an incredible orgasm while recalling the whole experience. Maybe the clerk knew I was buying for myself, or even pictured me wearing the items, and while that thought was thrilling, I always maintained plausible deniability.

  That all changed when I met Kristen. A free spirit and very open minded, the blond-haired, green-eyed beauty, at 42 three years my senior, was all about opening up with one another. She’d probe me for what turned me on the most, sometimes stroking me just shy of orgasm then stopping to ask me about one fantasy or another. In such a state, I was more than willing to open up, both for the arousal of the confession itself and the chance to cum in her appreciative, French-manicured hand.

  It was in just such a situation that I revealed my fantasy of shopping for myself at a lingerie store, only answering honestly when the clerk asked who I was buying for. That’s all Kristen needed to hear.

  In the ensuing weeks, we shopped in various malls in the region. Kristen would hold panties in front of my waist, ask pretty salesgirls what size would work “for him,” and, once or twice, cajole me into the fitting room with something very sexy. On those occasions, she’d insist that I stand in the doorway of the cubicle to model the garment for her…regardless of who else was nearby. Even when I tried to be discreet, and thought no one could actually see, she’d tell me later that the large fitting room mirror ensured my assets were on display to anyone near the fitting area entrance.

  I’d get lightheaded and my face would burn with embarrassment each time, but I complied, semi-hard, knowing that I’d be rewarded later when we got home. I had no doubt that I was the talk of the staff every time we left the store.

  Later, Kristen would masturbate me through the panties or the nylons, asking me if I enjoyed myself, and telling me how all the “pretty young girls were probably laughing at the perverted old guy getting hard in the fitting room.” I’d grunt in reply, but she’d stop playing with me until I admitted how excited it made me. Calling me a “pathetic sissy,” and saying she needed to keep me drained so I wouldn’t “harass any more Victoria’s Secret salesgirls,” she’d increase her tempo until I’d shoot a massive load all over her pretty fingers.

  All this, it would turn out, was prelude. Neither she nor I could have anticipated what would happen next, but if humiliating me to my very core was the goal, then Kristen, at least, would be more than happy with this turn of events.

  “I can’t find these in this color in Large, but they’re sooo pretty,” she cooed, loud enough to draw the attention of anyone standing within 10 feet. “I think you should try the Medium on, to be sure.”

  “Ummm…if you think it’s for the best,” I sputtered.

  “Oh, I do,” she replied with a smirk.

  Before I could think about it, she grabbed the hand not holding the panties and marched me to the fitting room, which at this moment was attended by a rather buxom brunette, with a pretty face and curves in all the right places. She was about 22.

  Don’t say it, I mentally begged, please don’t say it. There were too many women in the store, more than we’d seen most of the other times we’d shopped together. But I knew she would, and, if forced to admit it, some part of me wanted her to.

  “Hi, can you open a fitting room? My boyfriend would like to try these on,” she blurted. It was all so matter-of-fact.

  The clerk didn’t seem to know what to make of this, but smiled and began walking us down the fitting room corridor. There were three or four girls, some smacking gum and some wearing PINK-brand gym shorts, milling about, having just tried something on or waiting for a friend who was doing so. I also noticed a distinguished looking woman of about 45, her burgundy heels and grey pencil skirt indicating she’d come straight from the office, and holding a couple of wispy items in her hands.

  We made our way to the fitting room on the end when the clerk stopped and turned to us, as if she’d had an epiphany.

  “I’m sorry…um, men aren’t actually allowed in the fitting rooms,” she said.

  I felt relieved, but Kristen was dumfounded. I could see a bit of anger start to wash over her lovely face, and immediately knew my ordeal was not over yet.

  “Why’s that?” she said indignantly. Then, nodding her head toward me, “He’s tried on clothes in other Victoria’s Secret stores, and no one’s ever had a problem with it.”

  I couldn’t believe my ears. Hearing her say this in front of all the assembled women made me want to melt into the floor.

  “It’s just not consistent,” she added.

  “Well…that’s our policy here,” the brunette replied, politely. She was clearly taken aback by the whole situation.

  This exchange couldn’t have lasted more than five seconds, but it felt like five hours as the blood rushed into my cheeks and my cock, in spite of everything, began to stir. I felt a dozen eyes on me, piercing me. I also felt a tingling sensation in the area between my stomach and groin, that location that seemed to respond when I found myself in exceptionally embarrassing circumstances, from which there was no escape. More sweat beaded above my eyebrows, and my mouth suddenly felt parched.

  Now, not only was I the sissy seeking to try on panties in a lingerie boutique, I was an unwitting crusader…and the whipped boyfriend of a temperamental woman.

  “It’s OK, babe,” I muttered, turning to leave the fitting room.

  “No, it’s not OK. That’s…that’s discrimination,” came her response. “Come on.”

  With that, she grabbed my free hand once again and led me out of the fitting room. It was a brief, but welcome respite as we continued to browse the merchandise, with her marveling at how “ridiculous” the store’s policy was. She continued holding up various garments and asking my opinion, and I remained half erect, but I could tell she was distracted.

  After a few minutes, she approached the tall blonde we’d seen when we came in, and asked to speak to the manager. I cringed.

  “That’s me. I’m Becky. What can I help you with?”

  “Becky, my boyfriend would like to try on some panties, but the girl back there said he couldn’t use the fitting room,” she began.

  I stood there stiffly, unable to so much look at the face of the sexy store manager. It wouldn’t be an overstatement to say I was mortified. Several young women browsed merchandise within earshot. Why must she do this? I thought. Couldn’t she just let it be? Of course, I answered myself, that’s not Kristen.

  Becky’s hand went to her mouth as she stifled a giggle, a short squeal of feminine laughter that went right to my growing erection. Momentarily, she composed herself, with her eyes looking to the ceiling before zeroing in on me, then Kristen.

&nbs
p; Her voice was one of sympathy. “I’m sorry…we don’t permit men in the fitting rooms. Corinne is correct.”

  “We’ve been to multiple VS stores in three states, and this is the first we’ve heard such a policy,” Kristen protested. My knees felt like gelatin.

  “I understand,” Becky said with a warm smile. “It’s just that…it could make the other customers feel awkward.”

  “But it’s just not consistent. Either all the stores should allow it, or they should prohibit it,” Kristen went on.

  Becky stammered, grasping for something to say. Her eyes looked at me, first my face then, oddly, to my waist, then back to my face.

  “Maybe the other stores just weren’t very busy at the time he tried things on,” she finally said.

  Yes! I thought…that must be it. “Yes, they were never quite this busy,” I said helpfully, hoping to extricate myself from this predicament sooner rather than later.

  The two women ignored my comment.

  “And in any case,” Kristen said indignantly, “that’s just plain discrimination.”

  I groaned audibly. I wished she hadn’t gone there. Put Kristen on a soapbox, and it’s very hard to get her down. If I’m uncomfortable or embarrassed as a result, then she’ll stand her ground interminably.

  It was at that moment I caught a familiar body out of the corner of my right eye. I say body because it was one I saw regularly at my apartment complex swimming pool, belonging to a college-bound 18-year-old who liked to traipse around in black string bikinis, a small charm dangling from her navel. I’d spoken with Paige a handful of times, before backing off to a friendly “hello.” I surely didn’t need her thinking of me as the creepy old guy by the pool. Yet I couldn’t not look whenever her outer clothes came off.

  She attracted much attention by the pool, including looks of envy from the other women. Aside from feeling compelled to look at the navel piercing, I always noticed her pretty feet, and a rosary or some similar tattoo around her left ankle. I’d watched on several occasions as she smoothed sunscreen over her body, tongue practically hanging out of my mouth as she worked the area around that delicious bangle in the middle of her belly, until she’d glance up and I’d dart my eyes back to my book or newspaper.

  Paige was just the age to be into the Pink line of clothes, so her presence shouldn’t have surprised me. But in this situation, I felt deep embarrassment the moment she noticed me. She even seemed to do a double-take. The auburn-haired vixen was wearing a black halter top, khaki cargo shorts that contrasted nicely with her tan legs, and a pair of high-heeled wedge, open-toe sandals. As I was averting my eyes downward, I noticed the French pedicure I remembered seeing by the pool.

  “Isn’t that so, honey?” Kristen said, startling me back into this most humiliating conversation.

  “Um…yes,” I said, not wanting her to think I wasn’t engaged.

  “You see, Becky? Even he admits that the only one who feels awkward when he goes back there is him!”

  “Hmmm…then in that case…” I could almost see the wheels turning in Becky’s pretty head. A smirk spread over her lustrous lips. “Corinne, would you come here a moment?”

  The curvy young sales associate joined us.

  “Corinne, you were correct in not allowing this gentleman into the fitting room, but his girlfriend here makes some good points about discrimination,” Becky said. “I won’t open the company up to a potential lawsuit. Why don’t you go make sure he gets…uh…fair and equal treatment.” She smiled openly at Kristen as she said it, yet stared into my blushing face.

  “Right this way…sir,” Corinne said, stifling some laughter of her own. She led me toward the fitting room…and right past Paige, who looked quizzically at the scene unfolding in front of her. I caught her eyes for an instant, then once again looked down at the floor. What must she be thinking right now?

  “Oh and Corinne,” Becky called out, loud enough for just about everyone in the back half of the boutique to hear, “Be sure to take all of his measurements…waist, chest, everything. Just like you’d do for any female customer.” I don’t think I imagined it, the way she emphasized the word “female.” My cock stirred and a lump came to my throat. My cheeks simultaneously burned.

  “Wait, honey!” Kristen called out. “Don’t forget the panties!”

  I stood in shock, then had to will myself to return to her to retrieve the sea foam undies, which she’d snatched from me as she was making her point to the manager. I heard a snort come from Paige. Walking past her again, back toward Corinne and that dastardly fitting room area, I heard Paige say in a sing-song tone, “Don’t forget your panties.”

  Kristen followed as Corinne escorted me to a fitting room smack in the middle of the corridor, one door over from the office worker, whose empty burgundy heels were visible under the stall door. Two other girls were going in and out of fitting rooms. “I’ll be back to check on you in a minute,” Corinne said with a pleasant smile and a wink.

  I pulled the door closed, and in the “solitude” of the stall, and under a giant black and white image of a model in a garter belt, stockings and fuzzy mules, I stripped off my clothes and slid the silky underwear up my legs. I felt like I had no choice, not that it didn’t turn me on to do so. As I pulled them up, I felt I was succumbing to the will of not just Kristen, but Becky, Corinne and, yes, every customer in the store who’d heard the exchange.

  Suddenly there was a knock. “Honey, can I come in and see?”

  “I, um, well…” My dick was throbbing, and forming a noticeable tent in the front of the soft fabric.

  “Don’t make us wait, sweetie!”

  Us? Before I had a chance to respond, I saw the door handle turning. The door opened, and Kristen and Corinne were standing there. I tried to slink toward the rear of the stall, at least until they came in and closed the door. But they weren’t closing the door!

  “Oh, how cute those look on you,” Kristen clucked.

  Corinne stepped forward and looped her forefinger into the waistband, checking the fit. “You’re not bursting at the seams,” she said, “well, at least not around the waist.” Both women chuckled.

  As Corinne pulled out the tape measure and began wrapping it around my waist, I spied Paige lingering near the fitting room entrance, looking our way. My stomach was in knots, but my dick grew another inch. The clerk’s hands touching my waist, together with my protruding hard-on and the sexy smirk plastered on Kristen’s face made me emit a small moan. A moan of pleasure, a moan of resignation, a moan of complete and utter humiliation. The bracelet hanging from Corinne’s wrist brushed against my satin-encased erection, and I began to fidget.

  “Stand still for her,” Kristen commanded, wrapping her fingers around my barely enclosed cock, as if to calm me. “She needs to take more measurements, especially if we’re going to pick out a properly fitting bra.”

  Her words cut into me. A bra? This was going a little too far. I’d never bought a bra before. “That’s…that’s not really necessary,” I stuttered.

  “Of course it is,” Corinne replied. “Fair and equal treatment, right?” They both giggled again.

  I glanced toward the entrance to the hallway, seeking some escape route, but in my current state of undress I was basically stuck there. Worse, when I looked that way, I saw Paige staring right back at me. I averted my eyes from her face, only to see her manicured hand raise up the bottom of her black halter. While Corinne’s hands worked the tape measure around my upper body, and Kristen’s hand slowly and gently stroked my tent pole, Paige began tracing a circle around her navel jewelry with her middle finger.

  My knees buckled, and my back arched. In spite of my deep humiliation, and with my eyes locked on Paige’s slow-moving right hand, I began jetting cum against the sea foam panties that imprisoned my cock. The combination of release mixed with burning shame made me lightheaded. I grunted as I continued drooling cum into the underwear for 20 more seconds. Kristen never removed her hand.

&nb
sp; “I hope you like those panties, mister,” Corinne said, looking straight at me. “Cause once you’ve soiled them, you’ve bought them.”

  Peals of feminine laughter filled my head.

  Fleet Feet

  Never had I so anticipated a trip to the bank. I tried to time my visit so as not to get there during the lunch hour. My plan was to arrive in the late morning, then bide my time in line sneaking peaks at the legs and pumps of the branch manager, Liz Galino. Maybe muster the courage to say hello and introduce myself. Then drive the mile and a half home and beat off furiously.