Undercover Sissy Pt. 03

All character are 18 plus.

I shuffled into the office while my muscles were still sore from last night's escapade. Agent M was already seated behind her desk, her eyes scanning over some papers.

"Hey, Nicky, you're back!" Agent M greeted me with a warm smile. "How did it go?"

"Yeah, I think so," I replied, trying to sound confident. "Found a lead that might help us crack this case wide open."

"Haha, hope it's not as wide as your sissy pussy," she said. "We know you found an address for your next job but I meant how was last night sex?"

"You know how it was?" I replied. "You guys bugged that place a long time ago and still send me in that shithole."

"Yeap but except for one room. We don't have anything inside Snake's office," She replied. "We heard you had sex with Snake and he was quite satisfied otherwise he wouldn't gave you the address."

"You want me to go into detail?" I asked.

"Ofcourse," she replied.

"Is it necessary?" I asked.

"I can file a report that you're not listening to me," She retorted with a dramatic flair, teasingly implying consequences.

"Alright, alright, here it is," I replied with a hint of playful exasperation.

"Spill the beans, but keep it short and sweet," she said

"Then he pulled me on a table spreading my legs and started fucking hard," I replied, my voice tinged with shyness. "He then picked me up with his tool still inside me and took me on the chair."

"And you just started screaming, didn't you?" she asked, a smirk playing on her lips. "So, how long was his dick?"

"I felt him very deep inside me. It was an intense sensation, and at times, I could feel him all the way up to my belly button," I replied with a playful wink.

"Lucky girl. Next time, I'll use a tool to break the record," she said with a mischievous grin.

"Haha, challenge accepted! We'll have to see if the toy can keep up with you," I replied with a playful laugh.

"If you can keep going after my turn, you're more than welcome," she said with a confident grin.

"Then I might need to train for that marathon," I replied, chuckling at the playful suggestion.

"Damn, you make me rock hard," she replied with a flirtatious grin.

"Glad to hear it!" I replied.

"Too bad your tool doesn't get hard, otherwise I would've let you fuck me right now," she replied teasingly.

"Guess I'll have to find other ways to keep you entertained," I said.

"You're right, your tongue will work just fine on my wet pussy," she said with a playful smirk.

"Well, if you're offering, I'll make sure to put my 'talents' to good use," I replied.

"Good boi," she said. "Sit under my desk."

She pulled up her skirt and sat down in her chair. She slid her thong off and put it on the floor. I got down on my knees and crawled under her desk between her legs and then started vigorously licking her. She was wet and totally relaxed in her chair. I could feel her writhing around. I continued licking her and felt good about it, tasting her pussy for the first time. Suddenly she put both hands in my hair, pulling out my face from her pussy.

"Not too fast sissy," she replied. Then, she slid the chair back a little bit. "First worship my feets."

As I took up one bare foot in my hands, I marveled at how soft and smooth it was...so lovely to look at...so pleasant to touch. Then I started kissing her bare feet and it was enjoyable and I let her know that by the way I kissed them. I let my mouth adore her feet as I rubbed them. I started kissing them a bit more passionately. Her skin was so sweet and erotic. I pressed my lips into it in total worship. I was coming to adore her feet. It was wonderful having my hands and lips all over them.

"Mmmh, you're good," Agent M moaned.

Every sign she gave me emboldened me to go ever further in worshiping and comforting her feet. As I kissed her feet, I would part my lips and allow my tongue to play on them, to glide along every succulent inch. My kisses now encompassed licking as well....my tongue massaging as my fingers had done. As my lips slid along the side of her foot, they would suck gently and my tongue would flick at her foot. My kisses became open-mouthed, my tongue enjoying her feet...hopefully pleasing them as well. And then, kissing my way up to her toes again, I could no longer resist. I held her soft foot up to my lips and put them around her big toe, letting her toe slide between my lips and into my mouth. The toe's warm softness made my mind turn to mush. Reluctantly, I eventually let go of that toe, but then moved on from toe to toe, taking each one into my mouth and savoring the feel and taste of it. I sucked her toes slowly, and as I did I started

hand massaging her sole and instep, and even her ankles and heel.

As I soothed and worshiped her feet, I instinctively knew what she now desired. My lips still focussed on her wiggling feet, but my hands began to wander above her ankles,to her well-formed calves. As my mouth tended to her feet, my hands massaged and caressed her calves soothingly. My lips and tongue did their best to stimulate her lovely feet while my hands crept slowly up her calves, gently caressing their way up.

It was at this point that she became intent on a more active role in things. She took her foot from my grasp and positioned it on my shoulder, sliding her chair forward, putting her other foot on my other shoulder. Her sliding her chair further under the desk made me that much more cramped, but it brought her delicious thighs within easy reach of both hands and lips. Happily, I took this as a sign that she wanted me to explore more than just her feet now. So, gently rubbing the instep of one foot, and letting my other hand slowly caress her thigh, I kissed and nuzzled her calf as I rubbed both foot and thigh. I took my time rubbing and kissing my way up her calves and thighs. There was, after all, no need to rush.

My lips worked their slow way up to her silky thighs, and as I did so she once again sat back in her chair, shut her eyes and smiled contentedly. It wasn't long before her lush lips parted slightly and soft sighs escaped them, her breathing becoming quicker with each passing moment. I decided to go for broke. I might never have this kind of opportunity again, and she sure seemed to be enjoying things, so why not? I moved all of my stroking and kissing above the knee now, with a definite plan of moving as far up as I was allowed.

I stroked her calves and thighs and kissed and even licked her about mid-thigh. In the cramped space, getting to her upper thigh was a bit difficult, but well worth the effort. I even had to come slightly out from under the desk to give her inner thighs the attention they deserved.....and wanted. Since she was lost in her contentment, I had no trouble at all in pushing her chair back slightly to accommodate this.

I kissed and licked back and forth from one inner thigh to the other, and she seemed to appreciate it greatly. As I kissed her inner thigh, she lifted herself off her chair slightly and pushed herself forward, her tailbone resting very near the edge of her chair. She leaned back as far as the chair would allow and took her legs off my shoulders, placing them both on top of her desk. Once her legs were over my head on the desk, she spread them invitingly. I couldn't believe this was happening to me. I never thought Agent M would allow me suck and see her pussy at the same time.

For, as I raised her skirt to further access her creamy thighs, I saw her pink pussy. I stared at her curly tendrils and pouting lips in awe and with growing passion. Her hands came down and grabbed my head, ending any lingering doubts I might have had when she pulled my face down into her moist, warm crotch. I kissed it....gently at first...and then my lips became more passionate in their worship and exploration of her nest.

As with her feet and legs, my mouth soon was exploring all about her pussy...becoming more and more thorough in its probing and pleasing. I was lost in her scent and taste. My mouth kissed and sucked on all the juicy pink folds of her flower. I sucked on anything I could get into my mouth. My fingers spread her lips wide to allow my tongue to tease and titillate every moist inch of her womanhood. Her breathing was becoming still quicker and much more shallow, the sighs quickly becoming panting. Holding her open with one hand, my other hand grabbed her buttock and squeezed as my tongue explored her with abandon. I licked her slowly, then faster, letting her approach climax, but then pulling back somewhat, not letting her explode too soon. I wanted to prolong her pleasure as long as possible.

Nuzzling her musky nest, I sought her love canal and pushed my tongue into it, exploring its moistness. I licked inside her and brought my hand from her buttock to play in her juicy folds while my tongue danced inside her. I maintained this dual assault on her pussy until I felt the vibrations begin in her thighs, and felt her begin rhythmic movements with her hips. I played inside her a bit longer, but when I felt her hands tugging at my hair, and heard her gasping sighs, I knew it was time to set her free. Still stroking her soaked sex, I removed my tongue from inside her and brought my mouth to her clit, now peering from its hiding place and crying out for attention.

As my tongue gently touched and teased her clit, her hips began to rock a bit faster and her gasping became more labored. I teased her clit with my tongue as she rocked and sighed. Keeping her clit held captive between my lips, I now flicked my tongue at it, the tip of my tongue barely touching it. I moved my face up and down to keep pace with her rocking hips, keeping her clit warm and safe between my lips. Her hips rocked faster and faster and the trembling in her thighs was reaching a peak, but my mouth held her clit firmly, my tongue now flicking just a bit more forcefully on it. I held her button between my lips and began to suck gently on it as my tongue lapped at it.

When my sucking on her nub became more forceful, she moaned loudly and her hips bucked suddenly. I rode with it, not wanting to lose her clit and bring her down again. I licked and sucked wildly now, moving my face all around her pussy as my mouth gave her clit intense pleasure. Her hands tugged at my hair and her bucking almost caused them to rip some of it out. When she finally achieved orgasm, I rode with her as long as I could. Even as she came I kept sucking and licking to prolong it for her. She bucked and squealed with pleasure, and her squeezing thighs almost choked me in her passion. But, I hung on to the very end.

It was quite some time before her orgasms had ended and her trembling and spasming had subsided. I pulled my dripping face from between her now limp legs, but leaned for- ward briefly to kiss that delicious moist tuft of womanhood, grateful not only for the pleasure it had given me, but also grateful that I'd been able to give so much pleasure to it as well.

"That was wonderful," she said, "You're welcome to crawl under MY desk anytime! But always ask first like a good sissy boi. Understood?"

"Yes, Mam," I replied.

"I never thought you were this submissive; otherwise, I would've taken control over you a long time ago," she said, teasingly asserting her dominance.

"Well, I guess I'm full of surprises. Maybe it's time for you to unleash your dominance then?" I replied.

"That's it, from now on, you'll obey me like I'm your Mistress. Say 'Yes, Mam," she said, asserting her dominance in a playful yet commanding manner.

"Yes Mam, I'm yours to command," I replied.

"So, will I hear any complaints from now on?" she asked.

"No Mam, you won't hear a single complaint from me. I'm here to please you in every way," I replied.

"What about the tasks I'll give you? Will you question them anymore?" she asked, her tone a mix of amusement and authority.

"No Mam, I won't question your tasks. I'll carry them out to the best of my ability, eager to please you," I replied.

"That was unexpected. Anyway, I'm calling our boss to let him know you're ready for the side missions too," she said, with a hint of surprise in her voice.

"Sounds like I'm in for some exciting challenges then. Ready and eager to take on whatever missions come our way, Mam," I replied. "What kind of side missions are these?" I asked, curiosity lacing my tone.

"Understood, Mam. I await your orders eagerly," I replied.

"Now tell me the rest of your fuck session with Snake," she ordered. "Make it brief."

"Then Snake went on and on fucking me and I was screaming, he then made me stand and fucked me from behind. After a while he started sucking my pussy and limp clitty all together, this made me cum immediately. He then inserted in me and fucked; this fucking and sucking went on for 45mins I guess and my pussy was swollen with pleasure. I begged him to stop and allow me to catch some breath but he didn't. He put me on the floor lifted both my legs and staring in my eyes he started fucking me until he dropped besides me by cuming inside me."

"That was rough," she replied. "Then I guess this side task won't be any trouble for you."

Agent M called our boss and asked for a mission using a code name and then she wrote an address on a piece of paper.

"Before I give you the task I need to teach you how to be slutty and wear slutty dress," she said. "I think you may not need the slut training anymore so it's your wardrobe I'll focus on today. Are you ready?"

"Yes, Mam," I replied.

Agent M's eyes lit up with interest. "Good boi. But before we dive into that, let's make sure you're alright after last night. Come over here and let me take a look."

I approached the examination table nervously as Agent M gestured for me to sit down. She reached into a drawer and pulled out a medical kit.

"Alright, Nicky, I need you to undress so I can check you over," she said matter-of-factly.

My cheeks flushed with embarrassment at the thought of undressing in front of Agent M, but I knew it was part of the job. I quickly complied, trying to ignore the self-conscious feeling creeping over me.

Agent M began her examination, her touch gentle yet firm as she inspected each bruise and mark on my skin. "These bruises proved that you had quite the night," she teased.

I nodded sheepishly, feeling a mix of discomfort and relief. Agent M's presence always had a calming effect on me, even in moments like this.

As she continued her examination, Agent M asked about any discomfort or pain I might be feeling. I answered her questions as honestly as I could, grateful for her thoroughness and concern.

Once the check-up was complete, Agent M gave me a reassuring smile. "You're looking good, Nicky. Just make sure to take it easy for a bit, alright? Ohh, sorry that's not happening with you until it's me I guess."

Agent M put back her medical kit and sat in her chair. "Dressing like a slut is not that easy you're thinking. Just wearing a skimpy dress won't make you look slutty. But that is the first rule. If you're out to dress like a slut, show off more skin than you normally would. Whether it's legs, boobs, or short shorts, let it out. Crop tops will help you show off your body more. Short skirts are always in a girl's wardrobe. Pair them with some of the tops I gave you. Cleavage is the way to go if you're ready to dress to show off the goods. Pick up a nice push up bra and show off what you've got. Show off the cookies without showing them off by letting your bra show. Wear a lace bralette that can be seen, a sheer top as a shirt, or simply enjoy wearing a bralette as a shirt. Lace shirts. Lace bralettes. Lace everything. This single fabric instantly makes any outfit seductive in nature. Sheer tops can be worn overtop of another shirt, or as a shirt themselves. This is one of the items on the list that is pretty versatile, and a must-have for your new wardrobe. If a sheer top is a bit too much for you, pick up a light-colored shirt. Then, pair it with a bright or dark-colored bra to have some fun. Sometimes wear a shirt that says "Daddy Cum In Me" and you're good to go. Pick up some high heels to pair with any outfit. Thigh-high boots are another must-have. They are comfortable and can be paired with anything from shorts, to short skirts to oversized sweaters. Big earrings are not going to instantly scream sex goddess to other people, but they are a wardrobe essential. They'll look amazing with everything else on this list. Show off your G-string. Grab the sides and pull them up over your hip bone." she took a breath. "That's all. Go to this address and don't forget to wear something slutty."

"Ok Mam," I replied.

"Ohh Agent R will show you what to do sp no worries," she informed.

"Agent R?" I was confused. Agent R position was vacant for a long time. You need to show some good work to get that.

"Ohh, it's that rookie who joined you in your last mission," she mocked. "You should talk to him. I heard he's angry at you for not saying thank you after the mission. He did save your butt there. You almost got caught."

"I'll Mam," I replied. "But..."

"You're dismissed, Nicky," she stated firmly, her tone leaving no room for argument.

I quickly gathered my things and nodded, not daring to meet her gaze for too long. "Yes, Mam," I replied, feeling a twinge of nervousness at her commanding presence.

As I turned to leave Agent M's office, her voice stopped me in my tracks. "Hold on, Nicky," she called out, her tone sharp and commanding.

I froze, my heart pounding in my chest, and slowly turned back to face her, unsure of what I had done wrong.

Agent M fixed me with a stern glare, her expression unyielding. "You forgot something, Nicky," she said, her voice cutting through the silence like a whip.

My stomach churned with dread as I racked my brain, trying to figure out what I had missed. And then it hit me. I had forgotten to thank her for the examination.

"I-I'm sorry, Mam," I stammered, feeling a flush of embarrassment creeping up my neck. "Thank you for checking me out and training me for the next mission."

Agent M's gaze softened slightly, but her tone remained firm. "Remember your manners next time, Nicky. Gratitude goes a long way in this line of work."

I nodded, feeling chastised yet grateful for her reminder. "Yes, Mam. I'll remember."

With a dismissive wave of her hand, Agent M signaled for me to leave once again. As I hurried out of her office, I made a mental note never to forget to thank her again, no matter how small the gesture.

Agent M reached for her phone, a satisfied smirk playing on her lips as she dialed our boss's number. After a few rings, the call connected, and I could hear snippets of their conversation from where I stood outside her office.

"Boss, it's Agent M. I just wanted to give you an update on the latest mission," she began, her voice oozing confidence and authority.

I strained to hear the response from our boss, feeling a mix of curiosity and apprehension about what they were discussing.

"Yes, Nicky's finally starting to show some progress," Agent M continued, her tone tinged with amusement. "I've been working on breaking her spirit and making her more submissive for everyone's use."

My heart sank at her words, feeling a pang of betrayal at being talked about like I wasn't even there.

Our boss's laughter echoed through the phone, sending a chill down my spine. "Excellent work, Agent M. I knew I could count on you to handle this delicate matter with finesse."

I clenched my fists, struggling to contain my anger as they continued to discuss me as if I were nothing more than a pawn in their game.

"And let's not forget to thank Agent M for her exceptional work in this regard," our boss added, his tone dripping with sarcasm.

Agent M chuckled in response, a smug satisfaction evident in her voice. "Of course, boss. It's all in a day's work for me."