Next Time

Story Info
Panty wearing man returns to lose his virginity.
1.8k words
4.49
135.8k
43

Part 1 of the 4 part series

Updated 06/07/2023
Created 10/25/2008
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I hurried out of the building, my cock hard and dripping copious amounts of precum, staining the front of my slacks. I awkwardly attempted to cover myself with my briefcase as my mind raced. "Did that really just happen? Did one of the most powerful industrial giants just use me as his cumslut?"

I hailed a taxi and offered a generous tip to get me to my hotel as quickly as possibly. Ten minutes later and $30 poorer, I was safely enclosed in my suite at the Hyatt. I immediately removed my pants and lay down on the bed. My erection hadn't subsided at all. I stroked myself through the material of the thong. Mr. Richards body, his cock, his hands forcing my head down, consumed my thoughts. I pulled the thong back and quickly stroked my cock. On the fifth stroke, I erupted, shooting cum higher than I ever had before. I collected what I could from my stomach and tasted myself for the first time. I savored the second load of cum that I'd had in an hour, in my life.

Coming back to reality, I quickly wrote an email to my company, informing them of the good news and that I would have to stay in Denver through the weekend. I knew there would be no problem with this, afterall, I was about to land the largest account my company has ever had. I received a reply expressing my boss's gratitude for my hard work and his empathy for me having to stay over the weekend. He promised that he would make it worth my while. I smiled at that, wondering what he would think of the real reason.

Throughout the week, I received several emails from Mr. Richards, asking for clarifications on various points of my proposal. The tone of the emails was completely professional, with no hint as to what had transpired between us. I worked out daily and noticed that I had a new interest in checking out the bodies of men in the gym. I timed my workouts to be at the gym at the busiest times, ensuring that I would have an eyeful for my fantasies later in the evening.

On Friday morning, I went shopping for a new pair of panties, wanting to find something just right for my meeting. I finally decided on a pair of black lace boy cuts, which completely covered my cock and balls and hugged my round shapely ass. I bought one size too small and was too preoccupied to make any excuses to the salesgirl. I simply paid and rushed back to the hotel. I modeled for myself in front of the mirror, admiring how the panties clung to my ass, making it fuller and rounder.

At 3:45, I was again waiting for Mr. Richards. I could feel myself straining against the new panties and prayed that the receptionist wouldn't notice as she led me into the office. Once again, I felt very feminine in the overtly masculine room. The receptionist left me at the door and closed it behind her.

"Lock that door." I heard from across the room. I quickly obeyed.

"Now strip, let's see what you wore for me today." I started to slowly remove my clothes, taking my time, doing my best to be sexy for him. I turned around and slipped my pants off, bending over to remove them from my legs, and giving Mr. Richards a long view of my ass and balls encased in the silky panties. "Come here." I started to walk towards him. "On your knees!" I knelt on the floor and slowly crawled around his desk. I knelt before him, looking up in his eyes. Once again, just the smell of his cologne caused me to swoon and slightly loose my balance. His strong arms caught me and held me in position. I looked at him again and he nodded.

I unbuckled his belt, feeling the throbbing in his pants as if his cock were its own being, demanding release. I unbuttoned and unzipped his pants, then looked pleadingly up at my new Master. I wanted all of his cock, not just what I could reach through the zipper. He nodded his assent and raised his ass off the chair. I quickly slid the pants down, bringing his underwear with them. His cock jumped out, fully erect, 7 hard inches, precum already pooling at the tip.

My first instinct was to swallow his monster, but I felt more confident my second time. I held his cock in my left hand, slightly pushing up so his foreskin remained over the tip of his pink head. As I bent my head to take each ball in my mouth, I hoped that my plan would work...that the precum would gather on his head and under the foreskin, giving me a tasty treat when I finally worked my way up.

His hair tickled my cheek, as I took each ball in my mouth and rolled it around, loving the silky feeling of his scrotum and the hard lump in the middle. I tried to take both in, but they were so big, I had to be satisfied with one at a time. His intercom buzzed. I looked up scared, but his eyes told me to stay where I was.

"Yes?"

"Mr. Richards, I'm leaving for the weekend, will there be anything else?"

"No Monica, you can go. Have a nice weekend."

I moved down from his balls, softly licking towards his ass. His aroma was stronger here, the taste of sweat bitter on my tongue, but I eagerly breathed in and used my tongue to clean him. I felt him bend over and his hand reached my ass. A soft moan escaped from our mouths simultaneously as his finger lightly traced along my crack. He quickly pulled my head back with his other hand and I found his cock, now shiny with precum pointed at my mouth.

I slid my tongue again between the head and the foreskin, capturing his essence, savoring it. The taste activated my saliva glands and I drooled over the head of the manly cock in front of me. My mouth covered the head and I slowly began my descent. The foreskin gave way as he entered my mouth. I took about 4 inches in this time. I could already feel him at the back of my throat. I moaned around his cock and felt it jump. I stayed on my knees, slowly pumping him in and out of my slutty little mouth. I wished that I had lipstick to display my progress.

He allowed me to indulge myself for a few minutes, then gently but insistently pulled me up. He bent me over his desk, my ass now sticking out seductively. I had never been fucked before, but I knew that I wanted this more than anything. I wanted to be his woman, his slut, his bitch. I wanted to feel his hardness enter me and possess me. I would do anything for this man.

He rubbed my ass in ever smaller circles, finally pressing the silk panties towards my...god, I was thinking of it as my pussy. He gently lifted my hips and slowly removed my panties, exposing my ass to him for the first time. I heard a drawer open and a few seconds later, the coldness of lubrication began it's journey down my crack.

"Spread your cheeks for me," he softly commanded. My cock and balls felt crushed against his desk as I moved my hands to my ass, slowly spreading and giving myself to my new man. He placed a finger against me, teasing the outer ring before beginning to slowly push its way in. I gasped and felt my ass clench on his finger.

"So tight," he sighed and pushed his finger the rest of the way in. He waited a moment for me to adjust and then began to slowly finger fuck me. By the fourth or fifth stroke, I was pushing my ass back to meet him. He added a second finger, then a third, stretching my ass, preparing my pussy to accept him. Suddenly, he pulled out, leaving me with a feeling of emptiness and a desire to be filled.

I tensed as he stood behind me. I felt his cock rubbing along my groove. He leaned over and whispered, "Just relax, you're going to love this." I tried to relax as he lined up with my hole, but the initial pain of penetration caused me to clench on his head. He held still, caressing my back, allowing me to become accustomed to his girth. I willed myself to relax, needed to feel him take me, to shove himself deep within me and possess me.

When he felt me relax, the pressure increased and I felt his cock slide deeper inside me. This time he kept moving until I felt his pubic hair and balls resting against me. "Mmmmmm," I moaned, the pressure on my prostate causing a little surge of cum to spill onto the desk. He obviously took this as a sign to continue and began to withdraw. He pulled all the way out of me and then quickly split my ass again as he bottomed out in my ass. On the next withdrawal, I was ready and when he began to plunge again, I pushed my ass back to meet him. He then placed his hands on my hips and began fucking me with hard fast strokes.

"You like being my little sissy, don't you?" He gasped, flexing his cock inside me.

"Yes, sir. Please fuck me, make me your little sissy." I moaned, completely absorbed in the fucking I was receiving.

"You want to be my sissy? You want me to dress you up? Tell me how much you want me, you slut."

"Oh my god, sir. I will do anything for you, just please keep fucking me." I felt his cock pulse and immediately felt his hot cum fill my ass. I could hear it as he continued to fuck me, in and out, a little slower each time. When he finally pulled out. He grabbed me and pushed me to my knees.

"Stroke yourself as you clean my cock," he said, watching as my hand went to my cock and my mouth neared his. I could taste myself on him, pungent, but not unpleasant. My hand blurred up and down my cock. I leaned back and with a gasp shot my load all over the wooden floors. Without a word, I bent over and licked my cum from his floor.

"Come, get dressed." He said, tossing me my panties. "You have blocked off this weekend for me, haven't you?"

"Yes Sir." I said, scrambling to get dressed, still glowing from the knowledge that I had pleased my man.

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biazmbiazmabout 1 year ago

Waiting for the weekend now! What a great 'meeting'....

sissyrobin2000sissyrobin2000over 1 year ago

So hot one of my fantasies

cdCindy1cdCindy1over 6 years ago
great story

This story was such a turn on. Is there a prequel to this story? I seem to recall reading somewhere a "Mr. Richards" in a business setting and the writer of the story working on his account and then going to Denver for a meeting. Did you have a prequel story to this one? Please let us know. Thanks.

cdCindy1

liz33ndliz33ndabout 8 years ago

this moved way to fast. but still good story line. he goes from wearing panties to anal in super speed.

BadMarieBadMarieover 12 years ago
Just like my neighbor

Mr. Richard took control just as my neighbor, my sister's friends father did when he too took my anal virginity and made me his girl. I saw him most everyday till I left home at eighteen and then whenever I returned.

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