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Office Sex 6: Two Sissies Playing

"Two sissies talk and play."

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Author's Notes

"Another in the Office Sissy section of the Jennypout Stories."

Now that 'Becky' had fully revealed herself and played with me and others so openly, 'she' was very responsive to suggestions. So when I told her to come to my office the next morning early, there she was. In contrast to me, though, she was still wearing her usual boy's clothing, a suit and tie. I was in my usual girl's clothes, in this case, panties and a short-skirted cotton sundress with a halter top, short-heeled sandals, my short hair permed, my fingernails and toenails painted a matching pink, a little blush on my cheeks and a light pink tint on my lips. Under it all, I was already erect. I had an exciting morning planned for us, now that I had a true partner. First things first.

"Everything off, Becky," I said. "You shouldn't be hiding yourself in those stupid clothes, girl," I said.

He was new enough to this to blush a little when I spoke to him that way, showing his submission with his head down and eyes averted, embarrassed, and perhaps ashamed. But he obeyed. He immediately undid his tie and took it off, then unbuttoned his shirt and took it off, laying it on my desk. Meanwhile, I undid his belt and pants and pushed them down to his ankles. He was wearing panties of course, silky white ones, which was no surprise. As everyone had learned in the past two days, he had been doing that under his male clothes for years. I could see he too had an erection, so this was clearly exciting for him.

"Panties down," I said to him.

He immediately dropped them to his ankles. I bent down and he dutifully lifted one leg for me and then the other, as I slipped off his shoes and socks, then his pants and undies. I stood up and looked him over. He was nicely shaved smooth all over. I reached out and cupped his balls in my hand, then trailed a finger softly up the length of his cock. As with most men I'd been with, his cock was bigger and thicker than mine. As I touched him, he moaned, also softly, aloud. He also moved his hips a little, to press his cock against my finger. 'Becky' really was slutty, I thought, just like me.

"Let's be girls together this morning," I said, "and play. Ok?"

'She' nodded yes, even smiling at me.

I reached over for a quilted blanket I kept there and spread it out on the floor in front of the desk. I took off all my clothes so that the two of us were completely naked, then I sat down on the quilt and motioned for Becky to sit across from me. The door was open and anyone walking by could see us there. We could definitely be interrupted by anyone who had an interest in 'playing' as well. But at least for the moment, it was just us two.

I reached up to my desk drawer and took out the oil from the several lotions I had always kept there for my frequent mid-day masturbation sessions.

"Let's get ourselves ready to play," I said.

I squeezed the oil all over myself, not only my groin, belly and thighs, but also my chest and arms and hands. Then I did the same with Becky. I rubbed the oil to spread and smooth it in and he mimicked me, doing the same. In a minute we were both all smooth and slick and shiny. Then I moved closer to him so that our bare legs were touching. He was sitting with his knees up, his thighs spread apart enough so that I could see everything. I leaned forward and put one hand down to his butt, then touched his anus with a finger. He let me.

"Is this your pussy?" I said, in a soft, teasing, lispy, girly voice, spreading the oil from his wet thighs down between his cheeks and touching his hole with a slippery finger.

"Yeth," he said, slipping easily into his preferred delicious, incredibly subby, sissy persona.

I pushed my finger up a little, into him.

He moaned again, letting me enter him.

"Tell me how you felt yesterday, Becky," I said, "when Sharon was playing with you."

"I loved it," Becky said, still speaking softly. "I loved sucking on her nipples." He paused. "Then she touched me."

"She jerked you off," I said.

"Yeth," he said. "I made a cummy." He loved the cute talk, I noted.

"But you've been pretending to be a boy, all this time, until a few days ago. How was that for you, being in the office with the women here, all those years?"

"It was hard," he said, in his normal voice. "I usually wore panties under my pants. So I was excited a lot. And all the time, when I was around the women, I was looking at their breasts whenever I could do it without being noticed. Sometimes, one of them would notice and tell me 'eyes up here, Jim.' But they figured I was just being a guy, checking out their bust. They never realized."

His 'clit' was still erect, as he spoke. I took my hand away from his butt. I moved closer to him and put my legs over his, so that my feet were at his groin. I slipped a slippery foot under his butt so that my big toe was now right under his 'pussy'. I pressed my toe against him so the tip of my toe went into him a little. He moaned, perhaps with a little discomfort, but he didn't move away. Then I moved my other foot so that my sole was up against his cock. I looked at his face. His eyes were half-closed, with pleasure I assumed, and his mouth open. He moved a little so that his cock pressed against my foot.

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"You like that, Becky?" I teased him in my girly voice.

He nodded 'yes'.

"You like to be fucked and you like to suck cock," I said. "Have you done that a lot, have you always been gay?"

"No," he said, his voice normal. "I never did that until two days ago, with you. I've never been with a guy. But when I'm Becky, I'm just subby and girly, and I feel like I have to do whatever anyone wants to do with me."

"But did you like it?" I said.

"Yes," he said, nodding 'yes' again. "It made me come."

"Say it," I said, looking at him. He knew what to say.

"I like to be fucked," he said. "And I'm a subby cocksucker," he said. 

Meanwhile, he moved his 'clit' against my bare, slippery foot, and moved forward so that my big toe entered his 'pussy' more. He gasped and moaned. I noticed a little dribble at his mouth. I knew I could make him come if I wanted him to. But I didn't. I leaned forward and put my lips against his and kissed him, my tongue between his lips, our tongues touching.

When we moved apart, he said, in a soft voice, "Have you always been gay?

"Yes," I said. "Ever since I can remember, I thought about being girly with a boy. I had a friend with whom I used to play. He was bigger than me, and used to put me on his lap and touch me. I loved it. Later, when I was away being a counselor at a camp, another counselor used to play with me at night. I loved that too, sucking his cock, being naked in his bed."

Becky was stroking my back and shoulders as I talked. I ran my hands along her thighs. We were both erect, even without directly touching our cocks.

"But I'm really bi, more than gay," I said. "Because I always loved girls too, not just their clothes, but them. So I always had friends who were girls, and I dated too. I never had the nerve to tell girls about me, that I was bi, that I wanted to be girly, and wear girly clothes. I definitely never had the nerve to tell anyone how subby I was, or tell any girl that I loved touching and kissing her feet, which was part of being subby for me. But if I was with a girl and we were fucking, and I could touch their legs and feet as part of it, sometimes while licking their cunny, then I could move so that my groin touched their feet, and that was the best."

"What about telling someone," he said, meanwhile putting his hand up to my face and his thumb in my mouth. I sucked on his thumb a bit, then moved back to talk.

"Never told anyone," I said. "But I'd think about it a lot. And also about them peeing on me. So that's what I'd be thinking about working here, being around them, especially the ladies. And whenever I could look at their feet, especially if they wore sandals, or if their feet were bare, say if they were sitting and slipped off their shoes, I'd get very excited. It was hard for me, sometimes, to be talking with them, pretending to be a boy, an adult, while all the time being excited and wishing I could be their subby plaything, at their feet. So I'd end up playing with myself afterwards, a few times a day. I also tried to use the toilet after they did, a private bathroom we had in our section. If one of them went in, I tried to go in right afterwards, if I could. I'll drop my pants and just be in my panties. Then I'd kneel down in front of the toilet and just feel the warmth of the seat, where she'd been sitting. Sometimes I'd lick the seat. Just imagining that, being there in front of her while she peed or whatever, I'd be so excited!"

This shameful confession, even to another sub, excited me so much. Becky noticed and reached down to stroke my cock as I spoke. I moved up and back in his hands.

"You like foot-play with me, right?"

"Yes," I said. "But only because you're a sissy like me. Footplay with a real man doesn't do it for me. It really has to be a woman." I thought for a minute, while he was still touching me and my arousal was rising. "Maybe if you dressed up as a woman, that might be ok."

He was still pressing against my foot while touching me, and my toe was still a bit inside of him.

"Let me fuck you, Becky," I said. "C'mere."

I pulled him forward so that his butt was over my groin. I spread his cheeks with my hands and maneuvered him so that my fully erect cock was aimed at his hole. The tip of my cock pressed against his anus. He moved to help me and I entered him, just the tip. He grunted and pushed down. I entered him more. Soon, I was halfway in. I was only able to move a little but it was enough to be fucking him. Our heads were close enough so I could kiss him as we fucked, and I did that. Both of our eyes were closed, the two of us lost in the sensations. I didn't know it at that moment but we had attracted an audience. One of the women was at the door, watching us.

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Written by jennypout
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