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Laurie was a co-worker who had recently been appointed the training officer in our government agency. As such, she had acquired a nice private office, in which I found myself spending more and more time. We had always been friendly, but lately were exchanging comments of a more personal nature. I’d call it meaningless flirting. Laurie was a year or two younger than me, in her late twenties, tall and pretty, with legs that went on forever. I had always found her attractive, with a combination of beauty and brains that was rare, at least among the women I knew. The only problem was that she was married, and I assumed happily so. So I didn’t let my interaction with her, or even my thoughts, carry too far.
Nevertheless, when she offered me a choice of going to Orlando with a couple of guys for a weeklong training seminar, or to Atlanta with her in the same class, I quickly chose the Atlanta trip. I reasoned, to her, that I hadn’t been in Atlanta for a while and maybe we could catch a Braves game. Secretly I was thrilled to be going anywhere with Laurie for a week, even if it did involve a boring seminar.
We had separate flights to Atlanta and she was a little late arriving at the seminar’s hotel site on Monday morning. But I had saved her a seat and my day brightened when she arrived. We got through the class by writing each other little notes with funny comments, talking and laughing during breaks, and enjoying one another’s company despite the dry topic of the seminar.
After class we changed out of business casual into shorts and tees, met in the lobby, and went touring the city, on foot and by train. We found a nice Italian place for dinner, toured some more, and before we knew it, it was nearly ten o’clock and we were back in the hotel lobby. The hotel bar was nearby and I suggested a nightcap.
“Oh, I need to call home,” she said. Thoughts of her husband immediately brought me down from my day-long high, but just as quickly I was soaring again when she added “Robbie, why don’t you get us a couple of beers and bring them upstairs in about twenty minutes? We can watch TV a while. Okay?” She smiled and turned toward the elevators.
I couldn’t quite believe my situation, invited to her room so late in the evening. I considered just going up to my room and calling her to say good night, but I reasoned she’s calling her husband, for Pete’s sake. Just go spend a few more minutes with her. It’s all innocent, right? The bar let me carry two beers upstairs if I charged them to my room, so that was easy. I went to my room, brushed my teeth, put on a clean tee-shirt, found some ice for the beer, and waited for thirty minutes to elapse before walking down the hall and knocking on her door.
“I didn’t think you were going to make it. Come on in.” Laurie had changed into pink fleece shorts and a matching tank top. She was barefoot and truly gorgeous. “My pajamas, at least for this week,” she explained. She sat in the middle of the king-sized bed and patted the bed for me to join her. I kicked off my flip-flops and sat cross-legged next to her.
We sat quietly for a few minutes, sipping our beers and occasionally commenting on the events of the day. I stared vacantly at the television, not having the slightest idea what was on.
“You’re so shy,” she said softly.
“A lifelong problem, I guess,” I admitted. More silence, until I couldn’t stand it anymore.
“Laurie, this has been a really fun day. I’ve had such a nice time. With you.” I paused. “Would you…,” I fumbled for what I wanted to say.
“Would I what?” She smiled, almost shyly.
“I’m wondering…” My heart was pounding so loud I’m sure she could hear it. “Would it be okay if I gave you a hug?”
She didn’t say anything, but held out her arms and smiled. We leaned into each other and embraced tightly, falling to the bed after a few seconds. It was as though we had melted together, a feeling so rare it had to be right. Her cheek moved across mine and our lips found one another’s. We kissed deeply and passionately for what had to be a couple of minutes. She rolled on her back, pulling me on top of her as our kiss went on and on. Then, to my surprise and delight, she started pressing her pelvic bone against my swollen member. I started to grind back, dizzy from the realisation that only a few thin layers of fabric were preventing what we both wanted so badly.
We continued our frantic grinding, and I was certain I had never been harder in my life. Her hands moved to my lower back while I couldn’t move mine from her beautiful face and hair. Her movements became more desperate, until I felt her shudder and convulse, muffling her gasps against my neck. I held her tight until she relaxed her hold on me and gently pushed me aside, still kissing my neck, cheek, and lips. After a minute or two, her breathing eased and she sighed. She looked deeply into my eyes and smiled, the most beautiful smile I had ever seen.
“Did you…?” she asked softly.
I shook my head no.
“I’m sorry,” she said, gently kissing my cheek. She tickled my bare belly below my shirt for a moment, then stopped. “I’m sorry,” she repeated. “You know I can’t.”
“I know,” I said. By now my erection had subsided and I wasn’t feeling quite as desperate. I kissed her again. “I know.”
We snuggled for a while, Laurie’s hand stroking my chest under my shirt, with me revelling in the feeling of her breasts crushed against me. She brought her lips to my ear and whispered, “Can I see it anyway? Please?”
My head was swimming, filled with elation and dread. My fear made me lose whatever swell remained in my member. But I closed my eyes and nodded. She kissed me while her fingers undid the button on my shorts and eased down the zipper. She hooked her thumb under one side of my shorts and briefs while I grabbed the other. I raised my hips as together we pulled them down to my thighs, leaving me totally exposed. We continued kissing as she brought her hand up the side of my hip and rested it on my lower belly. She sat up on the bed and gradually shifted her gaze from my eyes, down my chest and to my groin. My penis was limp and tiny.
“Oh my,” she said, stifling a giggle. She immediately knew she had just crushed my feelings and didn’t know quite what to say. I could feel my cheeks and ears reddening and hoped she didn’t notice in the dimly lit room.
“It’s so cute!” she said, giggling again softly. That wasn’t exactly the right thing to say and my embarrassment only got worse. I imagined my penis shrinking even more. I shut my eyes tightly, hoping to hold back the tears that were welling up. Laurie lay back down and kissed my cheek, brushing a tear from my face.
“Hey, it’s okay. I love your little penis,” she whispered. She found another tear and kissed it away. “Can you make it big and hard again?”
“Huh?” was all I could muster in reply.
“Play with it, silly. Don’t you want to make it big and hard for me?”
I desperately did want to, but didn’t know what to say. “I don’t know, Laurie,” I sniveled.
She sat up and looked again at my shrivelled member. She giggled. “Come on, it’ll be fun. Play with your little penis for me.”
“Don’t keep saying that. It’s not that little.” I was gently weeping by now, knowing my humiliation was getting worse.
“Oh, honey, it’s okay to have a little penis. Is this why you’re so shy around girls?”
“It’s not that big a deal,” she giggled at her unintended joke. “Bet it’s a lot bigger when it’s hard. Five or six inches, I bet?”
I couldn’t believe this was happening, or what I was saying. “Almost four,” I said softly, “when I can get it up.”
She again stifled a laugh, and her demeanour was changing. “Oh, I bet you get it up all the time. How often do you masturbate your little penis?” She was obviously getting a kick out of saying “little penis.”
I decided not to lie about it. “Almost every day. Sometimes twice,” I whispered.
Laurie held out her hands. I clasped them and she helped pull me up, sitting me next to her on the edge of the bed. “Honey, it’s okay. Boys do it all the time. Why don’t you pull your pants off?”
I silently did as she asked, and she pulled my shirt off over my head. I sat there, totally naked, shivering from fear and embarrassment, my limp inch and a half of manhood resting on my equally small scrotum.
She took my right hand and placed it on my lap, where it completely enveloped my penis. “Go ahead, honey, it’s all right. Don’t you want to make your little penis feel better?”
I whimpered “Yes,” almost inaudibly.
“Are you sure you want me to watch you? Because I guess I don’t have to, and I know you’re really shy. I can leave for a few minutes.”
She was toying with me now and there was nothing I could do about it. “No, don’t go,” I whimpered.
“Ask nicely.” She giggled and kissed me on the cheek.
“Please, Laurie. Please watch me play with my little penis.”
“That’s a good boy.” She took my left hand and held it on her bare thigh as she sat next to me. “Show me how you play with your little penis. I bet it just takes two fingers.”
I grasped my flaccid shaft with my thumb and forefinger and began rubbing gently. “That’s just too cute,” she laughed.
I rubbed and pinched and wiggled it for several minutes, through her gentle encouragement and occasional giggles, but it wouldn’t stiffen a bit. More minutes went by. Still nothing. Finally the humiliation was too much and I started sobbing uncontrollably.
“Oh, sweetheart, it’s okay,” she said, climbing up on the bed and sitting up against the headboard. “Come up here.”
I scooted up and curled against her, naked and shivering, and buried my tears into her chest, just above the swell of her right breast.
“I’m sorry, honey,” she said softly, stroking my hair. “We never should have done any of this.” She paused for a minute. “It’s really late. Maybe you’d better go back and get some sleep.”
“Please no,” I blubbered. “I really want to… please let me…”
“You want to try again? Is that it? Do you think you can make your little dick hard for me? Is that what you want?”
I nodded against her chest. “Uh huh,” was all I could murmur.
“Do you ever have trouble at home getting your little penis hard?” Laurie asked. She placed her hand on my thigh.
“Sometimes,” I sobbed.
“Poor little boy.” She extended her little finger and briefly grazed her nail against my scrotum. “What helps, honey? What do you do when you want to masturbate at home?”
“Sometimes, I call a sex line,” I offered weakly.
“You do not!” she laughed. “That’s so funny. Do you have a favourite girl?”
“Yeah, her name is Katie.”
“How does Katie help you get hard?”
I hesitated, reluctant to spill even more embarrassment on myself, but I couldn’t help it. “She makes fun of my little peenie-weenie, and calls me names.”
Laurie giggled again. “You like girls to make fun of your little peenie-weenie? What kind of names does she call you?”
“Things like sissy and…” I couldn’t believe I was saying this, “…and panty boy.”
Laurie tried to keep from laughing, and I could feel my face turning a deep red. “Are you a little panty boy, Robbie? Do panties give you a little stiffy?”
“S-Sometimes,” I whispered.
“Do you wear panties all the time, or just when you’re trying to get your little peenie-weenie hard?” She couldn’t stop giggling.
“I wear them to work sometimes,” I said, still whispering and not believing what was happening.
“Did you bring any with you this trip”
“Huh uh. I wanted to, but I left them at home.”
“Well, tomorrow we’re going panty shopping, you sissy little panty boy.”
“No Laurie, please…” I started crying again.
“Oh, stop it. You need some new panties. Some lacy bikinis, maybe a nice little thong. It doesn’t take much to hide that little peenie-weenie, does it? What are you, a size five? Ooh, this will be fun. Maybe get you some cute bras, too. Okay? Dress you up like a girl? Would you like that?”
“No, please no, Laurie!”
“Oh, I think you’d like it, panty boy. Might as well be a girl. Can’t get your sissy little peenie-weenie hard for a pretty girl,” Laurie teased. “Dress you up in a little bra and panties like a little sissy fag. You’re a little sissy fag, aren’t you, Robbie?”
“No! Please don’t say that!”
“Stacey thinks you’re gay,” Laurie said, matter-of-factly.
“W-What?” Stacey was Laurie’s best friend in the office, single, about 25, and a real knockout. “She does not!”
“She thinks you’re cute, but she thinks you’re so shy because you might be gay. She said I should try to find out this week.”
“She thinks I’m cute?” was all I could offer.
“That’s what she said. She said she might like to go out with you if you’d ask her. But I doubt that’s a very good idea.”
“Why?” I asked.
“Well, apparently Stacey likes her boyfriends to be rather…” she giggled, “…well endowed. She wouldn’t like your two-inch peenie-weenie. You’d let her make fun of it though, wouldn’t you? She already thinks you’re gay. What if she saw your little baby penis? I can’t wait to tell her.”
“Laurie, please no,” I whimpered. At last I felt a rise beginning in my member as I continued stroking.
“Wow, Stacey’s got a mean streak in her. There’s no telling what she might do. She might have you come over, and her boyfriend would be there, and she’d say she was going to have a contest. The winner gets to be her boyfriend. The guy with the biggest penis would win. So she’d pull down your pants and show him your little peenie-weenie. Then he’d pull his out and, of course, his would be huge. Everyone would laugh, except you, of course. And you’d be staring at his big real man’s penis and your little dickie would get all hard. He’d probably push you down on your knees and make you kiss his big penis. Stacey would be laughing her tail off.”
Laurie was saying terrible things but her voice, somehow, remained so sweet. I was laying sideways across the bed, my head on her lap, whimpering “‘no’ over and over while she taunted me. My fingers were working furiously on my finally erect member.
“You with your little sissy hard-on, getting your face slapped by his huge dick. ‘Suck it, faggot!’ You’d be crying, of course, just like you are now, but you’d open your mouth. You’d be his little faggot cocksucker, wouldn’t you? You’d swallow his big load of cum. You’d lick it all up, from his dick and his balls…”
“Laurie…” I gasped before shooting my load on my leg. She giggled.
“Did my little sissy finally make himself cum? That’s it, get it all out. That’s a good little boy.” She stroked my cheek with one hand and put her other one down on my thigh. She scooped up some of the sperm on her finger and brought it to my lips. “Go ahead,” she said softly. I licked my cum off her finger. “You made a mess, naughty boy.” She gathered some more on her finger and I dutifully licked it clean.
Laurie got up and went in the bathroom and came back with a couple of tissues. She wiped my leg clean, then gently took my soft penis between her thumb and forefinger and wiped off the head, pinching it and wiping the little tip dry.
“It’s just so cute.” She smiled and kissed her finger, then touched her finger gently to the glans. “So cute.”
She pulled back the covers and patted the sheet. I didn’t ask, just crawled naked into her bed. She went back in the bathroom, came back out in a minute, turned out the light and slid in next to me. I held her tight and buried my face into her neck.
“Laurie, can we do this again sometime? Please?” I asked softly.
“We’ve got all week, honey. I’ve got plans for you, my sweet little sissy boy,” she replied.
“I love you, Laurie.”
I had never meant anything more in my life.
“I know, sweetheart. Good night, Robbie.”