tagTranssexuals & CrossdressersCocksucker: Crossdressing

Cocksucker: Crossdressing


Summary: Straight man is forced to cross dress and suck cock.

You do not need to read the first parts to enjoy this story about a straight man crossdressing in San Francisco. In case you are curious about how he ended up in this situation here is a brief summary of the first two parts of the "Cocksucker" series:

Chris, a married straight man, is stuck at the airport when his flight is delayed. While waiting at the bar he is slyly seduced by a younger man. After submitting to him in a restroom stall, he must complete seven humiliating tasks to get his wedding ring back.

Task one was to walk around with cum on his face until he got to his hotel room hundreds of miles away, and to tell the woman at the check in why he was late for his flight (I was sucking cock in the bathroom).

Task two was to service a very gay hotel clerk and begin his training as a cocksucker. He also gets his first blow job from a man. Disobeying an order from his Master also leads to a punishment that has him sucking an older man's cock.

Without further ado, the continuing adventures of a straight married man who is quickly discovering that he isn't as straight as he thought he was.

NOTE: Thanks to Goamz86, Robert and MAB7991 for editing this story.

COCKSUCKER: Crossdressing

I woke up in a sweat from the most surreal dream I had ever experienced. I have had many sex dreams in my life but they usually consisted of hot celebrities, Dallas Cowgirl cheerleaders or Hooters waitresses, but this one had me sucking a stranger's cock.

As I became more alert, my eyes went wide as I realized the crazy dream was no dream at all. I had actually done it...I had sucked three strangers' cocks, had given my wedding ring to a stranger, and had committed to doing seven tasks of humiliating obedience to get it back. I had already gotten through two, but still had five more to go.

Looking at the clock, I saw that the alarm was going to go off in three more minutes, so I shut it off and jumped in the shower as I recalled yesterday and all the sin I had committed. I was mortified by my weakness, stunned by my eagerness and alarmed by the tumbling dominoes of consequences that had transpired because of one day of bad decisions. I decided yesterday was an anomaly and I was going to pretend it didn't happen.

I got dressed, had an overpriced breakfast at the hotel restaurant and was heading to the first keynote address, thankful I had gotten a room at the conference hotel, when my phone buzzed.

I checked it:


Ready for task three?

A chill went up my spine at the simple sentence. Using all the will I had, the need to respond shockingly strong, I put my phone back in my pocket without answering and headed to the auditorium for our first keynote speaker.

Just as I reached the auditorium, I saw Kevin, my boss, who was chatting with someone whose back was to me.

Kevin waved me over and I went to join the conversation. Just as I arrived, the gentleman conversing with him turned and my whole body faded of colour. The man Kevin was talking to was the man I had given head to last night in his hotel room.

He recognized me immediately but didn't say anything as Kevin introduced us, shocking me to my core.

"Chris, this is my dad, James. He drove up from San Diego to see me," Kevin revealed.

I stammered, raising my hand to shake his, all the while thinking 'I sucked your dad's cock last night', "H-h-hi Mr. Carson, nice to meet you. Kevin has told me a lot about you," which was true. His dad had overcome cancer two years ago, just in time to watch his wife die of cancer herself. I imagined I was the first one to touch his cock since his wife.

James squeezed my hand firmly, "It is a pleasure to meet you," stressing the word 'pleasure'.

"How long are you in town?" I asked, praying it was just for today.

"All week," James said, "hanging with Kevin a bit, doing a little sightseeing, and maybe trying new things," he finished while looking directly into my eyes.

Kevin added, "Yes, tell him Chris. To live it up, be reckless."

"I was rather reckless last night," James said.

"Sure you were," Kevin said. "What did you do after we left the bar? Stay up past eleven?"

"I was up until around then," he shrugged, the innuendo aimed at me. It was around eleven when I'd left his room after taking a load of his cum in my mouth.

Kevin said, "Oh shit, I need to meet Amy. Chris, please entertain my dad for a few minutes."

My face flushed at how I had already entertained his dad. "Will do," I nodded, even as Kevin walked away.

James said, "You're a very good entertainer."

"I'm so sorry, Mr. Carson," I said, mortified that the one stranger I sucked in this whole hotel was my boss's father.

"Sorry?" He asked. "I had forgotten what it was like to get head."

"I don't usually do that," I said, which was true.

"Well, I am hoping you do it again," he said.

"But your son is my boss," I pointed out.

"He said to entertain me. You would just be doing as you were instructed," he said.

"I don't think he meant for me to give you head," I countered.

"Semantics," he shrugged. "Actually, I think you should entertain me now."

"What? No," I said, even as my stupid mouth began to water, constantly betraying me.

"As I recall, you declared yourself a cocksucker and a real cocksucker doesn't say no," he said. "There is a bathroom on the third floor. Meet me there in five minutes," he ordered, before adding, "cocksucker."

My hunger to submit and obey apparently much deeper going far beyond just Gary, I nodded, "Yes, sir."

"Good," he said and left towards the elevators.

I took the stairs, wondering how I kept getting myself into a deeper more complex mess.

Reaching the third floor, I saw James enter the bathroom, and I followed suit. The bathroom was empty except for the two of us.

"Hurry up, cocksucker," James said. "We can't miss the opening speech."

"Yes, sir," I obeyed, hurrying into the last stall. James already had his cock out and I, after locking the door, dropped to my knees and took it in my mouth.

"Oh yeah, cocksucker, I bet Kevin would love to have his own personal cocksucker at work when he needed to relieve some stress and shoot a load," James said, as I bobbed back and forth on his cock. The thought petrified me, my job now officially at risk. Yet, the thought of being under Kevin's desk, sucking his cock, while he was on the phone or in a meeting popped into my head and turned me on even more.

"I bet you would love to be at the podium during the keynote speech sucking the speaker's cock while he spoke to a whole room of suits, wouldn't you?" He asked.

The idea was silly, but instantly I imagined doing exactly that. The opening speaker, William Hedge, was a black man and I instantly wondered if all the stereotypes were true.

"Here comes my cum," he said, this time grabbing my head with his hands and fucking my face. The feeling of his balls hitting my chin as he face-fucked me only enhanced my submission. My cock was dying for release from the rough treatment and naughty talk as he shot a load of his seed down my throat.

Pulling out, he patted my head and said, "Thanks, cocksucker."

For some reason wanting to shock him, I said, "Thanks for fucking my face and coming down my throat."

"Ever taken it in the ass, cocksucker?" He asked, putting his cock away.

"No sir," I answered quickly.

"Too bad. I think you would make a very cute faggot," he said, before walking out and leaving me still on my knees.

The word 'faggot' was a slap in the face for some reason. Cocksucker turned me on, but faggot made me feel gay. I shook my head at the absurdity of my own thoughts as I got up and made my way back to the auditorium.

I had felt my phone vibrate a few times while on my knees, so I checked my messages. They were all from Gary.


I don't like waiting.


I think you like being punished


I think maybe I should call your wife...her name is Laura isn't it?


Or maybe better yet your son. I believe he goes to my college. Is he a cocksucker too?

The threats making my stomach queasy, I quickly texted back:


Sorry sir, my mouth was full...of cock. The stranger I sucked yesterday is my boss's dad. Anyways, suffice to say, he just took advantage of this newfound knowledge to blow his load in my mouth in a bathroom. I will always obey and answer!!!

I kept walking to the auditorium and took my seat just as the day got started.

Of course, that is when the next text came:


Task 3: Go to a lingerie store and buy yourself the following....

The text ended there. I was nervous at what he was expecting but also curious. I vaguely listened to all the generic introductions as I kept waiting for the rest of the expectations.

I was about to text that I didn't get the rest of his text when I got another one. It was from my wife, and I felt a huge rush of disappointment.

Love you.

It was sweet and usually I would have smiled, but waiting for the rest of my task from Gary was all I wanted.

I quickly texted back:

Keynote speaker talking...love u 2

 I waited ten more minutes, anxiety building at the waiting for the unknown...before another text finally came:

6 pairs of pink panties. At least one should be a thong and another should have girly flowers on them.

I couldn't believe that was what was expected. Did he expect me to wear them?

I tried to focus on the keynote speaker, who was apparently funny based on all the laughter around me, yet I couldn't concentrate on his voice. Then another text came:

Three pairs of pantyhose in different colors. They must be real silk.

Then another text:

A matching bra.

Then another text:

You will try these on and ask a worker there how you look in them. You will tell them your Master wants you to look like a girl.

My cock was rock hard, my face pale and my mind spinning. There was no way I could do this.

Then another text:

You should also buy a pair of thigh high stockings for easy access to that man cunt of yours.

'Man cunt'? Did he plan to fuck me eventually? I couldn't fathom his massive cock fitting into me. The idea, ludicrous and disgusting less than twenty-four hours ago, suddenly seemed possible and slightly erotic.

Then another text:

You will wear the bra, panties and pantyhose under your clothing the rest of the conference. You will sleep in them as well. You are no longer a man. You are a cocksucker...a girl...a slut...a bitch...a whore...so dress like one.

I gave up trying to listen to the keynote as I tried to come to grips with not only the task ordered, but the obvious future expectations for me and my raging hard-on as I read the derogatory terms. I also shivered at the thought that this was only task 3.

Another text came a few minutes later:

Of course, I expect a picture sent to me of you dressed as my girl.

The keynote eventually ended and I figured that until I finished this task I would not be able to focus. I was having supper with Kevin, as planned before the trip, and whoever else he invited (I prayed his father wasn't one of them), so I couldn't complete the task after the sessions for the day were over. So I skipped my next session and Googled lingerie stores on my phone. There was actually one just a few blocks from where I was and I decided to go for a walk and enjoy the fresh air.

As I was walking and enjoying the scenery of downtown San Francisco, I got another text. I eagerly pulled it out only to see it was my wife again. I loved my wife, but the strange sense of disappointment I felt when it wasn't Gary was strange.

I clicked on the message:

Hope you are not just sitting around listening to boring presentations. Be a risk-taker baby. Do something that isn't you...skip a session and do something fun.

I smiled at how strangely parallel her texts and words were to what was actually currently happening.

I texted back:

Oh, I am really living it up here.

Reaching the lingerie store, I took a deep breath and walked in. The store was relatively empty, with a couple women giggling while looking at sex toys. I went straight to the clothing section and was instantly overwhelmed with the massive selection of panties to choose from.

 I was there less than a minute when a very pretty redhead, who couldn't be more than twenty, asked, "May I help you, sir?"

"Um, I need to buy six pairs of pink panties. At least one needs to be a thong and at least one must have girly flowers on them," I answered, the words sounding as absurd out loud as they did when I first read them.

"Oh, okay," she said. "That is a very specific order."

Deciding to just get the awkward part out of the way, I said, thankful I was in San Francisco, "It is what my Master instructed I get."

"Oh, they are for you then?" She asked, not acting surprised. Again, thank God I was in San Francisco.

"Yes, ma'am," I nodded, even acting subservient to a saleswomen.

She went to a table and grabbed a few pair. Handing them to me, she said, "These are our newest, silkiest panties."

"Thanks," I said, taking the variety of pink shades of panties.

"And a thong," she said, moving to another table. "Hmmm, most thongs are not made for men but I think this will work."

She handed me a fluorescent pink pair. My facial expression of the brightness must have been obvious as she apologized, "Sorry, the rest of our thongs wouldn't keep your penis in place."

"No problem, it's just very bright," I said.

"I'm sure he will love you in it," she said, talking to me like this was normal, which I suppose in San Francisco it was.

"Um, I also need a matching bra, three pairs of silk pantyhose and a pair of thigh highs," I added, figuring it would speed up the process.

"Mmmmmmm," she paused, looking me up and down. She moved to the bras and brought out a couple including one that was more of a girdle. She asked, "This may sound insulting, but is the bra to wear to humiliate you or to make you look like a girl?"

It was an embarrassing question, especially when asked by such a pretty young woman. It also was awkward because I really didn't know the answer. "I'm not sure. He did say he wanted me to look pretty and he calls me his girl."

"Well, I would suggest this pretty lace number if he just wants to make you look girlish, while I would go with this girdle that gives you breasts if he wants to transform you into a girl," she said.

"Transform me into a girl?" I repeated as a question.

"Well, he may want you to dress up as a real woman with breasts," she said, before adding, "and this will give you some very nice, voluptuous looking breasts if you had breasts forms."

"Oh my," I said, this getting crazier by the second.

"You can try it on if you wish," she offered.

"Actually, I am supposed to try on a bra, panties and pantyhose," I said.

"Oh," she said. "Well, the panties and pantyhose you would have to buy, of course, but the bra and girdle with breast forms you can try on first."

"Of course," I said.

"Go to changing room four and I will bring you some pantyhose," she instructed.

"Thank you," I said, taking my panties and other garments with me.

In the changing room, I got completely naked and looked at the tiny panties. I grabbed a pair of pink panties with little coloured flowers on them and slid them up my legs. My cock, semi-hard, was outlined completely by the tight panties. I stared at the bra and the girdle and decided to put the pink lace bra on first, I had it on my arms when the saleswoman knocked on the door.

"I'm sliding three pairs of pantyhose under the door. I would suggest the mocha coloured ones if you are wearing pink," she suggested.

"Thanks," I replied, taking the packages of pantyhose. I put them on the chair and continued to try to put on the bra. It was awkward, frustrating and, I eventually decided, impossible as although I could put it on where it should be, I couldn't come close to clasping the buckle on the back.

Leaving it half way on, I opened the package with the mocha pantyhose and sat down. This too ended up being an adventure. Eventually, after just trying to pull them on like socks, I recalled Laura bunching them up and slowly rolling them up her legs. I tried that, and eventually got them on. Once on, I couldn't resist rubbing my legs, in awe at how soft and sexy they felt, my own cock growing, struggling to get breathing room in its confined place in both panties and pantyhose.

Then there was another knock on the door. "Are you having any problems with the bra, sir?"

I laughed softly at the ridiculous contradiction of bra and sir before responding, "I can't get the bra done up."

"Open up," she said.

"Okay, I'm only in panties and pantyhose," I warned.

"Just open up," she repeated with a heavy sigh.

I opened the door, and she quickly slipped in and clasped my bra on. "I was hoping to see the girdle," she said, holding something that could best be described as breast implants.

"I'll try that on next," I replied, wanting to please her, too.

"Good, I think you will look hot with some tits. Now turn around," she said, so my back was to her.

I did, my cheeks again going red with embarrassment.

"Hmmmmm, super cute," she said. "I think, your Master will be very pleased."

"Can you take a picture of me in this for him?" I asked.

"Sure," she said, still not surprised by the surreal situation.

I pulled out my phone from my dress pants; I realized by bending down I gave her a long look at my pantyhose-clad ass. I turned around and handed it to her.

"Smile," she said, taking my phone.

I did, as she snapped a couple of pictures. "Actually, if you want a full body picture, we will have to move to the hallway."

"Um...okay," I said, not wanting anyone else to see me dressed like this or see the undeniable bulge in my panties.

"Don't worry," she said, "this is San Francisco, this isn't even a two on the shock scale here."

"Okay," I agreed, following her out of the dressing room.

"Okay," she said, "now pose like you would if he were here to see you."

Without thought, I dropped to my knees.

"Oh my," she laughed. "I was thinking just a sexy pose, but this is even hotter." She snapped a couple pictures before instructing, "Now one more with you standing up, hands on your hips and posing as if you want him to see all of you."

I did as she told me to, arms on my hips, legs spread a few feet apart and with a smile on my face as if I were a model.

"Sooooo hot," she purred, as she snapped a couple more pictures. Once done, she said, "now go and try on the girdle, and I will get you a dress and heels to go with it."

"Yes, ma'am," I nodded, both turned-on and mortified, a relatively constant contradictory sensation the past twenty-four hours.

I returned to my stall and realized I couldn't get my bra off. I sighed as I looked at the girdle. It was huge. I also realized I couldn't do it myself, so I waited for the salesgirl to return.

A couple of minutes later, she returned and said, "I am betting you couldn't get the bra off by yourself."

"No, ma'am," I admitted.

"Open up," she instructed.

I again did as she instructed and she quickly unclasped the bra. "Hand me the girdle."

She assisted me in putting it on. Once on, she grabbed the jelly looking breasts and said, "These are extra large breast forms and will give you very voluptuous, show stopping, tits."

"Okay," I said, as I was dressed up like a slutty Barbie doll.

Report Story

bysilkstockingslover© 25 comments/ 250750 views/ 124 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: