Successful Businesswoman Ep. 02

Nicole had promised to stay longer at work; I stayed longer as well, but for different reasons. When eventually we were the only people remaining in the office part of the facility I called her to me.

"Nicole, with your transition and the possibility of a relationship, I consider our chastity contract no longer valid. Of course you are still eligible for the productivity bonus."

"You're my key holder, boss. It's your decision to release me or not."

"I know, but I also want you to understand my reasoning. Four days in chastity isn't much, but I consider that less important than your transition."

"I understand, boss. I enjoyed the sense helplessness and dependance that came with the chastity, but I agree with you it's no longer necessary."

"There's one more motive that drives me. I'm curious how an erection would look on a sexy lady like yourself. After I see that I want to know how good you're with tucking."

"I won't disappoint you in any of these."

Nicole slowly took off her skirt to reveal a pair of sexy lacy panties in the same colour as her skirt and heels. She pulled the panties down as well, so the cute pink chastity cage finally got revealed. I took out the key from my drawer and we both moved towards the couch, I sat on it and Nicole stood before me with her legs slightly apart. I could not help myself and caressed her smooth nylon covered skin; I appreciated the sexy undeniably feminine look of her legs, but I also noticed and enjoyed the details of built and musculature that reminded me that I was still dealing with a man. The uncommon mix of femininity and hidden masculinity was surprisingly attractive for me.

I reached my hands behind her, so I could grab her buttocks; at the same time I leaned forward and planted a gentle kiss on the chastity cage. My caress was getting the desired effect, it might have been only several days in the chastity, but Nicole was clearly aching for a release. I did not bring her here to tease her, so I stopped all the play and opened the cage. I was not an expert with such devices, but I knew well enough to take it off gently, especially after this short foreplay; Nicole's penis was already beginning to get as hard as its prison allowed it.

After I took the cage off I began to gently lick the cock; it was still sensitive after the imprisonment and the skin needed to rest, it was eager to play even though its owner was trying to hold back her enthusiasm. My licking quickly became successful and within only a dozen or so seconds I was rewarded with the sight of Nicole's erection.

"You were hiding that beauty the whole time?" I asked in awe.

Not that the penis was so huge, it was longer and thicker than average, but most of all it was straight and had perfect proportions. To put things simple - it was the most beautiful penis I had ever seen; and I had seen a lot of them.

As soon as I begun a regular fellatio, Nicole's cock got fully erect and began to drip pre-cum like crazy; it seemed that few days in chastity are quite a lot after all. I would not be myself if I did not brag about my deepthroating skills, when Nicole's penis got sufficiently wet, which happened in no-time, I took it deep into my throat and held there for several seconds. You already know my favourite pattern, so I will not repeat myself here.

Just like Jeff at the Sex shop, Nicole tried to hold back her orgasm, but failed ever worse than the clerk; Jeff had not been locked in a chastity after all. But she beat him in another competition when she ultimately erupted, Nicole's load was so voluminous that I could not contain it whole in my mouth and some of the semen dribbled out of the corners of my mouth. I swallowed the rest, then collected the seed from my face with my fingers and licked them clean.

"Thanks, boss, you're amazing. I'll do my best to earn that."

"You'll begin right away, we aren't done yet. I want you to return the favor."

Two minutes later I was moaning loudly and Nicole's tongue and fingers were pleasuring my clitoris as she knelt between my legs. I was wondering how she had learnt such skill while being single. The girl Nicole had met online was going to be truly satisfied when they eventually have sex; but for now it was me who was enjoying this beautiful crossdresser's oral talents.

Nicole brought me to a magnificent and loud orgasm, my whole body rocked and I even squirted a bit, which I do not usually do. I spoiled her make-up slightly, but she did not seem to mind.

"Thanks, boss, once again."

"Thank YOU, Nicole. No more chastity for you, tuck it up nicely."

Friday was THE day and I found it hard to focus on anything else but the incoming poker party at Mark's apartment. To hold my libido at bay I put on a more conservative outfit for work, in my case it means a skirt that ended five centimetres above the knee and a modest blouse without a cleavage. I still wore twelve centimeter high patent heels and sexy lingerie, but at least I was not provoking too many lewd thoughts, in my own head at least, I was not sure about my employees.

The whole day at work went relatively uneventful; I once again had a pleasant conversation with Nicole and could admire her tucking skills. Émeraude called during the day and informed me that the party starts at eight, but it would be nice if I could come an hour or two earlier, so we could discuss the course of the evening. I agreed to be there at six, dressed in my new clothes and with a bag full of newly bought toys.

I arrived at Mike's house two minutes before time, my heart was racing. There were no cars on the driveway, so I assumed that his was in the garage and I was the first to arrive. My assumption proved to be wrong when Émeraude greeted me in the door, not that I was disappointed. Mark complimented my new outfit and we had a lengthy discussion by the wine. It was pretty obvious from the very beginning that the whole event would not end with just a card game so sex was the main topic. Since I was supposed to be in the center of attention I was the one to ultimately make any crucial decisions. Both of the girls and Mike as well had a lot of ideas, some of them quite plain, other more kinky. We discussed all the yeses and nos as well as some maybes, a safeword was set, the basic one - "red". After the talk we, the girls, left Mark alone and went to the toilet to get ourselves a proper bimbo look.

All three guys arrived together in one car a minute before eight. Of course it was I who went to the door to welcome them. I was dressed in my new bodystocking, dress and heels; I had a slutty make-up and did not look much older than the other two girls who were in their mid twenties. The men were glad to see that I was the surprise that they had been told about earlier. We were introduced to each other by Mark; the other cops' names were: Connor, Marcus and Josh. Connor was the guy who had made a joke about Émeraude's earnings as a hooker; it seemed that they were friends and such jokes were completely acceptable. Of course I received a fair share of compliments regarding my good looks.

Markus looked just like Eddie Murphy when the comic was in his prime, the wide smile and the outgoing personality. He was of average height so in my killer heels I was several centimetres taller.

Josh was of similar height, he had a cute face, the bluest eyes imaginable and a mop of fair hair; all that made him look almost like an actor from a teenage musical.

Connor was tall enough to look me directly in the eye, he had a lean athletic posture and a military haircut, but a single smile and a few words were enough to negate his otherwise serious appearance.

"Samanta wanted to join us for the night" explained Mark "but she's not a huge fan of poker, so together we came up with few ideas how to spice up the party. But before we get to the details and the game itself let's have something to drink."

Mark brought the guys cold beer while the girls drunk wine. The cards waited on the main table, but for now we sat by the coffee table. We, the girls, occupied the couch, while the guys sat on chairs; we made some friendly small-talk and the men ogled our sexy bodies shamelessly.

"We're going to play poker as usual, but this time Samantha will provide us with additional entertainment. From beneath the table, with her mouth."

I gave them a seductive smile and took it from Mark:

"I'm going to spend two minutes with each of you, then move to the next person. This way everyone will be tended to and you won't... ekhem... get too excited, too quickly."

"But we don't want to be selfish" picked up Mark "so we got tools to give Samantha some entertainment as well."

As he said that the girls brought two sex toys, one was a fifteen centimetre long vibrating anal plug, the other a similar in size vaginal vibrator. Both could be controlled with the same remote; Ashley also held a bottle of lubricant. The plan was that I would put both toys in front of everyone. I had had sex with half of them already, but the other three were still almost strangers; and having any kind of larger audience when using sex toys is a bit embarrassing, no matter how good one knows them. It would not only be embarrassing, but also slightly humiliating, after all they were still fully dressed and I was about to expose my most intimate parts. All of those combined made the deed even more exciting for me, every passing minute while I thought about the upcoming 'entertainment' made the lubricant less necessary, at least concerning the vaginal vibrator.

With my cheeks red, visible even under the makeup, I hiked up my dress and pulled down my panties (we had decided against a C-string since it would not be able to hold the vibrator in). Émeraude had lubricated the toys when I was undressing and now they were ready to be inserted; I bent at the waist with my back towards her. The anal plug went in first, carefully since it was pretty thick; I made an audible moan when the widest point passed my sphincter. My pussy accepted the toy more eagerly. When they were both in I pulled up my panties, straightened up and fixed my dress. I was rewarded with few whistles and catcalls, in current circumstances I treated them as compliments. There was just one more thing I needed to put on before going under the table - knee pads. They might not have looked too sexy, but neither did red knees or a run bodystocking; carpet or not, prolonged kneeling was uncomfortable.

Above my head the cards were being dealt as I crawled to my first 'client'. The rule says 'ladies first', so I picked Émeraude; I could not see her face, but she remained silent as she spread her legs invitingly. The crotchless pantyhose were not an obstacle and her panties were made of little enough fabric that they did not need to be taken off; I simply pushed them aside and I had the access to the policewoman's pussy. I was not able to remain equally silent when Émeraude turned both of the vibrators on; it was only slow speed, but a moan escaped my mouth nevertheless. It was loud enough for the people by the table to hear and they reacted with few lewd comments, which only made me hornier.

I began to work on the policewoman's clitoris with the same speed as the dildos vibrated - slowly; I wanted to tease her rather than rush for a climax. Few kisses, some gentle licks... and the two minutes were already gone, the timer on the table notified everyone about the fact. I crawled to Ashley and like with Émeraude I just moved her panties aside.

I went as slowly as with the previous girl, but the ebony beauty wanted to speed things up for me and she turned the vibrations up, this time I managed to remain silent even though the change was significant. Ashley was more active with the toys, she turned them up and down once in a while as I tried to focus on her clitoris. The two minutes passed almost instantly again. As I was crawling away from the policewoman she turned the vibrations to maximum; that made me give a loud cry which was welcomed with even more lewd comments.

Marcus would be the first man that I attended to, he turned the vibrations down only when my lips touched his penis. I was relieved and disappointed at the same time, but did not have the comfort to ponder on the vibrations, since I had a wonderful penis to take care of. I still remembered Mark's incredible size and it seemed that it was a feature which came with that name in the police. Markus was huge, I had easily made him hard during the two minutes and he was clearly over twenty centimetres long and proportionally thick. I did not try to deepthroat him already, but knew that it would not be easy. Marcus was not as active with the remote as Ashley, he had once turned it up, but soon turned it down again. With the vibrations at minimum I crawled over to Josh.

The blue-eyed cute had an average sized penis, at least when flaccid. But as I slowly worked my lips and tongue on it the cock began to grow... and grow... and grow! Before the two minutes had passed Josh's penis had gotten almost as big as Markus'! What was this, a police poker party or a porn set? The policeman was also significantly more active with the remote, he clearly found amusement in toying with my holes. Before I moved to Connor I was moaning audibly. I was seriously curious if the next policeman would match his colleagues' size, it would be either a large coincidence or... destiny. If I was turning into a complete slut who if not huge-cocked guys to accompany me?

Connor did not disappoint, he might not have been as long as the rest of the men, but he was thicker; and keep in mind that the others were not thin either. Once his penis had gotten fully erect I had to stretch my mouth almost to maximum to make it fit; his testicles matched the girth, I could only imagine the cumshot. Connor was not too active with the remote, but turned it up significantly right away and kept at that level for the whole two minutes.

Eventually after ten minutes of kneeling under the table I reached Mark. The final man on my route decided to be as active with the remote as Ashley. It might been that or just the overall excitement that had been piling up which eventually pushed me over the edge. I halted the fellatio and cried loudly in ecstasy so that everyone could admire how much of a screamer I was. I also held the leg of the table with one of my hands so they could feel the trembling of my body too; it was met with cheers and more lewd comments. When my orgasm finally subsided the two minutes were over, but my duty under the table was not; Mark turned off both dildos, but they remained inside of my holes.

I moved to Émeraude and began another round of oral service. This time I wanted to do more than just tease all of them, although I was aware that bringing someone to an orgasm in such a short time was going to be really hard. Both vibrators remained off for the duration of the whole second round, but they got once again turned on as round three began. The vibrations were distracting, but I still tried to do my best to make the police officers climax. Ultimately I failed (at that at least), but I was confident that they had to focus hard not to orgasm and it must have impeded their play. I was not trying to avoid climaxing myself, so again by the end of the third round I had an equally loud orgasm; it was also a sign to get out from beneath the table.

I got from under the table on wobbly legs, straightened my back and took off the kneepads. Almost forty minutes on my knees were uncomfortable, but the excitement made up for it with interest. My tongue and mouth were tired and my pussy needed a rest after being stretched by a vibrator and experiencing two orgasms, so I just sat on the couch with my legs spread in an unladylike fashion and took out that one toy. I am not sure if that was the cause, but the Eddie Murphy look alike who could see me best from his position dropped out first. My rest was not going to last too long.

Markus clearly was not regretting the loss that much and approached me with a wide smile on his face. I matched his smile, but feigned modesty at the same time and crossed my legs.

"What would you say for a consolation prize for the loser?" asked Markus "you could finish what you had started."

"Maybe... on the other hand, you could return the favor" I replied without changing the pose.

"With pleasure! Just spread your legs and you'll be moaning in no time."

"Not so fast" I might have spent three quarters under the table sucking and licking, but right now I felt a bit more dominant "how about you start at my feet?" I dangled my foot at the last words.

Markus seemed to be happy with either solution, he knelt before me and kissed my foot while caressing my calf with his palms. The rest of the people continued to play poker as Markus slowly progressed upwards along my nylon covered leg. He did not spare the kisses nor the licks and seemed to be enjoying the fact that I was wearing a bodystocking. He went along the outer side of my leg and eventually reached the hip, from there he kissed his way almost to my crotch where my crossed legs touched. I gently pushed him away, uncrossed my legs and put the other one on top, then I motioned for the policeman to resume the caress, this time of my second leg; he was happy to oblige.

When Markus again neared my crotch I did not push him away, but spread my legs invitingly instead; he eagerly accepted the invitation. I raised my hips slightly so he could take my panties off, he sniffed them before throwing them away; I had the feeling that I would not be wearing them anymore that night. Marcus poked the dildo in my anus, but left it in place. Before he begun the cunnilingus he turned the vibrations to minimum, so that my ass would receive some attention as well.

The policeman was skilled with his tongue, he clearly just wanted to tease me, just like I did during the first round under the table. While he licked my clit his palms roamed over my nylon covered legs. Since Markus' aim was not to bring me to an orgasm I did not climax before the next person dropped out of the game; it was Josh. With another player switching the game we had to switch our combination as well; the cute blonde got between my legs while Markus got up on the couch and took his cock out of his trousers with obvious intentions. I decided to continue the teasing game and went slowly on his penis, there was some kissing and a lot of licking, I fondled his testicles with my palm, but did not do any deepthroating. Marcus seemed to be satisfied with the fellatio at first, but I could be a real tease so he eventually run out of patience.

"Come on, Samantha! Don't be such a tease. Take me deeper."

Since Josh was doing a really good job himself I decided it would only be fair if I passed on the favor. Marcus' penis was already sloppy so taking it into my throat was not a problem despite its considerable size. As was my custom once my nose touched the man's underbelly I paused and stayed like that for several seconds. Marcus was clearly impressed and praised my skill:

"On damn, girl! You're good."

The 'good' was yet to come though, I began a regular deepthroating, with each motion taking almost the entire length of Marcus' cock out of my mouth and then 'swallowing' it whole until his testicles rested on my chin. After the initial teasing the policeman was really close to an orgasm, he needed just a minor push to get him over the edge. Once I sensed that he was nearing climax I pulled his penis out of my throat into my mouth; I continued to lick it while also stroking the shaft and fondling the balls. I was soon rewarded with a sizable load of semen, I made sure to collect every drop in my mouth before swallowing, then licked Marcus' penis clean.

"Thanks, baby. You're the best" he said in a breathless tone.