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Office sissy 4

"Two sissies find each other in the office"

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Author's Notes

"4th in the Office Sissy section of the Jennypout Stories. @Copyright jennypout1976."

It was the third day at the office, in my new role as the office sissy, and with the new rules, which allowed anyone there to play with me. I was in my office as usual, but I had brought more clothes in. So this time I was in a bikini, meaning a thong bottom and a bikini top holding my flat titties. Both were in matching light pink, which always seemed the right color for me these days, and the thong was barely enough in front to cover my usually at least semi-hard 'clitty'. I had thin pink tongs on my feet as usual, showing off my polished pink toenails, my fingernails a matching shade, and still my only makeup being the pink lip gloss. The only other girly touch was my hair permed into soft curls. And I was keeping my body completely shaved smooth, including my groin and, in back, my 'pussy'. In all, I was very girly, very open about it, but in every other way doing my work as usual. I was just waiting, to see who would use me next.

At some point during the morning, Jim showed up. He was one of the guys there, a numbers guy like me, and I assumed he wanted his cock sucked, something a hetero guy might do. But when he came in and said hi, he then closed the door and what he said surprised me.

"You know, jenny," he said, using my girly name, which I liked, "I envy you." He smiled and hesitated before going on.

"Envy me?" I said.

"Well, yeah. Because I figure you don't know this - I've been good at keeping it to myself - but I lot of the things you described - your secret thoughts, your desires - are things I've felt, myself."

I was really surprised. He was attractive, a fit guy in his forties, with good hair and a nice face. Whenever we had occasion to speak, or even when I just saw him around, I had fantasized about being his sub, about being on my knees, sucking his cock, or being fucked by him. I had similar thoughts about most of the guys in the office. He was no exception. But I definitely thought he was straight. That was how he presented himself. But now he was telling me something very different.

He wasn't doing anything other than continuing to talk to me, but I felt my usual arousal begin. Something was going to happen, for sure. "Tell me more," I said. "What things?"

He wanted to tell me, clearly. He leaned back against the desk, relaxing a bit, then let it spill. "Well, like the way you're dressed. I've never told anyone this, here at the office, or anywhere, but sometimes under my clothes, I like to wear panties. And when I do, I picture being with a guy. I'm pretty sure I'm gay, but I've never done anything about it. I could never be like Scott, who's so open. I've even dated girls, and never with panties on! But now that you've come out like this, it's really affected me. So I wanted to tell you."

I stood up and moved over to stand in front of him. I reached out and put my hands on his belt, just resting there, not undoing it. He didn't stop me, just stood there. I looked up at him and smiled. "Are you wearing panties now?"

'"Yes," he said, and I could tell by his tone that he was excited.

"Let me see," I said and undid his belt. Then I unzipped his pants and opened them a little. I saw he had on purple cotton jockey-style panties. I could also see that he had the start of an erection. But I didn't touch him yet. I wanted to talk more - that was always part of it, for me. He had his hands at his side, not touching me, but clearly ok with what I was doing. My voice soft, and lispy, being little girly jenny, as I always yearned to be, I said, "And when you're in your panties like this, are you a woman, or a ittle girl like me?"

He answered, and his voice was softer now. "I'm like you," he said.

"What's your name, little girl?" I said. I touched his erection with a finger, softly trailing it up to the panty-covered tip.

He moaned and I could feel his cock move a little in the panties.

"My name is Becky," he said, his voice not only soft now, but I could also detect a little lisp, similar to mine.

I felt a surge of arousal. I loved playing with other sissies! I moved up close to him and let the tip of my clitty touch the tip of his. I moved a little against him. He sighed, didn't move away, and I thought I felt his cock harden a little. Staying there like that, I moved my lips up to his and brushed our lips together. He opened his mouth and I licked at his lips, then gently kissed him. His eyes were closed as we kissed.

"Just two little girls, kissing," I whispered when we parted a bit.

I moved my hands to his waist then pushed his pants off his hips, so they dropped to his ankles. I knelt down and slipped off one of his shoes - he let me, lifting up his foot, then I removed his sock, then did the other foot. Then I pulled his pants down to his feet and he stepped out of them. I moved my face up his groin and nuzzled his pantied erection against my cheeks. Then I licked, wetting his panties. He moaned.

"Yes," he said.

He had a very nice penis, longer than mine, with a round, circumcised tip. I took the tip between my lips. I loved sucking cock, the smell and feel of a cock in my mouth, the way a cock responded to touch, hardening and moving a little. But it was really the act of cocksuckiI ng and what it meant that excited me even more than the physical part. I loved the idea of being a cocksucker, especially of being on my knees in front of a guy, of feeling submissive and girly, of doing for a guy what a girl would more naturally do.  I especially wanted to make a guy come and have his come in my mouth and over my face. But I didn't want to make him come right away. Having another sissy to talk to was too delicious to have quickly over.

"So tell me, Becky, does being a little girl mean you want to have a mommy? Or is it a daddy you want?" 

"A mommy," he said. "I said I was just like you. But a daddy could play with me too."

"Good girl," I said, cupping his balls in one hand and using my other to tease his cock. His hands were still at his sides, so I could see that passivity was part of his fantasy. "So all the time you've been in the office around the women, have you been fantasizing about them, thinking of them being mommies for you, being little Becky with them?"

He nodded, then said "yes" in that soft lispy voice and at the same time I could feel his 'clitty' jump in my touch, showing his excitement in expressing these delicious, forbidden thoughts, so openly. I knew what to do to play with him.

"Listen to me, Becky," I said, in a firm tone. "Take off everything but your panties. I want you to be a good little girl now."

He stepped back a bit and took everything off, then just stood there, his panty-covered bulge now showing a firm cock in the undies.

"You're a naughty little girl, Becky," I said, "so I'm going to spank you."

He gasped. I turned him around and began spanking his buttcheeks, turning them pink. He didn't do anything to stop me. Then I turned him back around.

"You're a naughty little cocksucker, aren't you?" I teased. I sat down and pushed him down to his knees. He went down easily. He was kneeling between my thighs. "Tell me what you are," I said, "tell me, Becky."

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He looked down at the floor but I could hear him clearly, in that soft voice. "I'm a little cocksucker," he said.

"That's right," I said, "you're a little cocksucker."

I pulled my thong aside and freed my hard 'clitty', then moved up a bit to put my tip at his lips. He opened his mouth and I pushed the tip in. He let me, pressed the tip of my cock between his lips and then I felt his tongue lick me. I pushed more into his mouth and began a little fucking motion. Meanwhile, I moved my foot between his legs and touched his hard cock with my toes. He moaned aloud.

I didn't want to come that way. I pulled back. He stayed on his knees. "You want your little pussy fucked too, don't you?" I said. He didn't say anything. "Don't you?" I said again. "Turn around," I ordered. "Show me your pussy."

Now he scrambled around on the floor, still on his knees, turning so his butt was toward me. I reached up to my desk for the lotion I kept there. I squeezed a liberal line of it between his cheeks, making sure some went directly on his 'pussy'. Then I put my hand between his cheeks and spread the lotion so his cheeks were glistening and smooth, and his 'pussy' well lubricated. He moaned again and pressed back against my hand.

"Tell me what you are," I said. "Tell me."

He sighed, I assumed with pleasure and the sheer intense feeling of openly sinking into the role he craved, his true nature.

"Yes," he said, "I'm a sissy, a fuckable sissy. Please, please fuck me." He was sincerely begging. This was what he wanted.

I bent over him from behind and rubbed my erect cock between his cheeks, slippery with the lotion. I put my hands on his cheeks and spread them a bit so I could get at his hole.

"I'm going to fuck you in your pussy," I said. "Ask me," I said. 

He replied immediately, his voice deeper with lust, but still the slight lisp telling me he was in his little girl zone. "Yes, please," he said, "fuck my pussy."

I pushed forward and let my tip enter him. He was tight. I pushed harder. He groaned, but didn't move away. "Are you a virgin?" I said.

 "Yes, yes," he said. 

"But you want this?".

"Yes, please," he said again, "please fuck me!"

I moved my hand to his hips and pulled him back into me so that my cock entered him more. I moved slowly but insistently forward until I was halfway in. He kept making sounds, pleasure mixed with discomfort. I stopped at halfway and began fucking him. Every time I pushed he responded with a noise, like 'oh' or 'uh', and I could tell from the pitch of it that he was being girly, in his mind, that he loved being fucked, that he was being little Becky, that this was his pussy I was fucking. 

But I didn't want to come in him this way. So I stopped and started pulling out. He actually moved back against me, trying to keep me in him. But I pulled out all the way and stood up. He was still kneeling. I moved to the side of him and brushed my cock against his cheek. He turned his head to kiss my cock. I was tempted to let him clean me, and then to come in his mouth. But I wanted to play with him more, to see how open he'd be about his sissy desires.

I kneeled down next to him. I could see his cock was fully erect, his face was flushed and he was breathing fast. He was very excited. I reached out to touch his cock and he moved in my hand, touching himself that way. I put my thumb in his mouth and he sucked on it.

"That's a good little baby, Becky," I said. "You're a good little girl."

He kept sucking on my thumb, and licking it.

"Let me show you something." I reached up to my desk drawer and took out some catalogs I kept there. I had always kept some catalogs at work, so that during the day, with my door closed, I could look at the pictures of beautiful women with bare feet and excite myself. Sometimes when at work in the past, I had actually closed my door, undid my pants, and used the lotion I kept there to tease myself, or even come, while looking at the photos. I wanted to see whether 'Becky' was arousable that way.

"Let's play a game," I said. "I call it, Mommy, Sis or Me. Let's look at these pictures and decide whether you'd like the woman in the photo to be a mommy for you or a sister, or whether you'd like to be her."

He nodded and smiled. I showed him some of my favorites, one by one. They were all beautiful, of course, but different body types. Most were barefoot, but some were in open-toe shoes of different kinds. These were photos that excited me. I would imagine being at their feet, a submissive sissy for them, licking their toes, pleasuring them. Sometimes, aroused, I actually licked their feet in the photo, which touching myself! I wondered if 'Becky' would have the same response.

I showed him one of my favorite photos, the woman in the picture tantalizing, in a short nightgown, with bare legs and feet, her toenails lightly polished.

"I wish she was my mommy," I said. "What about you?"

He looked at the photo. "Yes, a mommy," he said, his voice soft, eager. His cock was in my hand and moved a little.

"When I'm a little subbie girl, I like to look at mommy's feet," I said. "Do you, little Becky?"

He smiled at me. "I like these," he said, pointing at the model's bust.

"You like mommy's titties?" I asked, the two of us using our little sissy lispy voices. He nodded. "Do you want mommy to feed you?" I asked. He nodded again. "Are you a little baby sissie?" I said. 

"Yeth," he said, "I'm a little baby sissie."

His cock swelled a bit in my hand. I sat down on the floor and took his hand to pull him toward me. He was sitting between my legs now, his back to me. My own hard cock was against his lower back. I was able to reach around his waist to play with his cock. His hands were at his side, so he was open to me, letting me touch him.

"You're just a little baby. sissie," I said, touching him, teasing him. He moaned and moved himself in my hand, letting me masturbate him. He felt warm. I put my fingers in his mouth, wetting them, then back to his cock, teasing him. He kept making noises of arousal, little gasps and sounds. I knew I could make him come, talking this way.

"You should tell all the mommies here that you're just a little baby sissie, and that little Becky wants to be nursed, to suck on their titties. You should tell them, Becky." His movements began quicker as I spoke to him this way. "I know you want to, don't you? Let me hear you say it."

He spurted a little pre-come and made bigger movements up and down in my hands.

"Oh, mommy," he said, "pleth mommy, please let me be your baby sissy., pleth, pleth ...  " And he began to come, his juices flowing over my hands, his hips moving back and forth against me, my own cock jerking against his back, the whole scene, and his new openness about being a little sissy exciting me too so that I also began to come, my juices flowing out against his lower back, and dripping down between his buttcheeks, while he kept moaning, and gasping and making little sissy noises as he came.

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Written by jennypout
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