I could not believe it. The woman behind the front desk told me again, “We are sorry sir, but we have no reservation for you and the hotel is completely booked for the whole week because of the meetings and retreat for a major financial institution.”
“I know!” I said. “I am supposed to attend those meetings and participate in the retreat! Please, help me out here.”
I felt like a fool. I was holding up a long line at the front desk and I knew that I had forgotten to make the reservation. I was picturing me spending a week in a cheap motel down the road somewhere while all of my co-workers were enjoying a luxury resort. I would also miss out on the networking with the upper tier executives of the company who were so important to my career.
I had been through the same drill with the woman behind the desk several times and I was really starting to believe that she had no room for me.
Then, I heard a familiar voice behind me say, “If this young man doesn’t mind sharing a suite, put him in one of my extra rooms in the penthouse.”
I turned and saw Jackson Jennings, the famous hedge fund manager who was going to be the keynote speaker at the company meeting. He stuck out his hand and introduced himself and said, “I have enough room in my suite for an army and I wouldn’t mind a little company in between golf and a little work if you don’t mind sharing a room.”
I was stunned. Jennings was a financial superstar. He had made billions by his mid-40s. He was the darling of the financial television networks because he was tall, handsome, smart and charming in a down home pleasant sort of way. He was raised in Austin, Texas, but was educated at MIT and Harvard. He was probably asked to be the keynote speaker as a way to get a chance to talk to him about our bank providing some kind of services to his hedge fund.
I stumbled and stammered and managed to finally say, “My name is Joe Miller. I appreciate your offer, Mr. Jennings. I desperately need a place to stay. Are you sure it is not too much of an inconvenience for you?”
Jennings said, “First, call me Jackson. Second, I have stayed in this place before and this suite is so ridiculously big, we may not see each other for days.”
So, Jennings slapped me on the back and said, “Come on, Joe. I will show you your new home for the week.”
Jennings turned to a gorgeous blond girl who could have been a model and said, “Misty, will you make sure Joe’s bags get up to the suite? Thanks a lot.”
Misty smiled and said, “Sure, Jackson.”
On the elevator ride to the penthouse, Jackson said, “You probably think that Misty is employed by me because she is drop dead gorgeous and can suck a cock better than any porn star.”
I didn’t know what to say other than she was very pretty.
Jackson laughed and said, “Misty is gorgeous and she used to suck my cock before she got married, but the truth is that she is a genius and is better at her job than anyone else I could possibly find. She also has a good attitude and will put up with me. She runs my life.”
I was then 28 years old. I had been married for three years to a great looking girl and I was a junior executive at the huge international bank having the retreat at the resort. I was trying to become an investment banker. This was a dream come true to meet Jackson Jennings.
We were at a luxury Florida resort and top executives from around the word had gathered to meet and play for a week at company expense. I was a former college football player and I sometimes wondered if I was invited to these retreats because I was a scratch golfer.
I am about 6 feet tall and was a very fit 175 pounds. I had lost about twenty pounds since college when I was a wide receiver and running back. I have short blonde hair.
Jackson showed me around the penthouse. It was huge. It had a huge living room, a full kitchen, several bedrooms and baths in addition to the master bedroom and bath which were beautiful and gigantic. He gave me one of the extra rooms and told me to make myself at home.
Jackson opened a bottle of red wine and poured me a glass. I had never tasted anything like it. Jackson laughed when I asked him about it and said that he did not concern himself with stuff like what wine to buy. He left that to Misty.
Jackson said he was going to clean up and would see me in a few minutes. I heard the shower running while I drank a second glass of the superb wine. I truly could not believe how good it tasted.
Misty came into the suite a few minutes later. She asked me if everything was okay for me and I told her that everything was great. She then asked, “Does Jackson still have his clothes on?”
I gave her a perplexed look and said, “He did the last time I saw him, but he is taking a shower now. Why did you ask?”
Misty smiled and said, “I just wanted to warn you that Jackson spends a lot of time when he is not working in the nude. He doesn’t care who sees him. It throws some people off.”
I told her, “If I can stay in this suite and drink this wine, I don’t care what Jackson wants to wear around his suite. He doesn’t go nude in front of you does he?”
“Oh, yeah. All of the time. But, I have seen it all before and I have an understanding husband. The huge paycheck Jackson gives me helps my husband be understanding.”
Misty asked me about my job and my wife and I asked about her husband and her interesting job. I really liked her and I could quickly see that she was very bright and very charming. Misty said that since Jackson had taken me in, I needed to understand that everything that goes on around the suite this week is confidential and cannot be revealed to anyone including my bosses and my wife.
Misty said that one of her main jobs was to avoid securities law violations. She laughed and said that she also had to protect Jackson from the gossip magazines to the extent that was possible. Jackson was constantly seen with super models and beautiful young actresses. The gossip magazines could not resist a handsome billionaire with a super model.
Misty laughed and said she felt like a pimp keeping track of all of Jackson’s women. I told her that from what I had seen in the papers she was doing a good job.
About that time, Jackson came back into the living room. He was naked and was drying his hair with a big white towel. Jackson looked great. He was muscular and tan. He obviously worked out a lot. He also had a partial erection and the biggest cock I had ever seen hanging down between his legs.
I had seen a lot of naked guys in locker rooms over the years and I had never paid much attention to their bodies. For some reason, I became instantly aroused by Jackson’s body, especially his big cock. It was huge and thick and it looked great swinging between his legs as he slowly walked in drying his hair. I was literally weak in the knees. I felt like I might fall down. I also was somewhat embarrassed that I instantly had an erection. This had never happened to me from looking at a man.
Of course, lovely Misty was seeing the same thing I was. I found it exciting that Jackson was showing his big dick to this beautiful girl.
However, this was apparently old hat to Misty. She said to Jackson, “You are walking around with an erection in front of your guest! Can you cover that thing up, please?”
Jackson laughed and said, “Oh, Misty. You have been doing that to guys for years. Maybe you could help me out with this erection.”
Misty rolled her eyes and said, “You didn’t even know I was here. And, you know I don’t want to help you with your erection problem.”
Jackson laughed. “Too bad you had to get married!”
Misty said, “I have good news for your erection problem. Alberta is flying in to see you on her way to New York. I am just guessing that she knows what to do about an erection.”
Jackson smiled and said, “Great! Joe, you will enjoy meeting Jenny, she is a lingerie and bathing suit model from L.A.”
I was confused. “Who is Alberta?”
Jackson laughed and said, “Alberta Einstein is Misty’s nickname for Jenny. Misty does not think that Jenny is too bright. That may be true, but she has other redeeming qualities.”
Misty turned to me and said, ” Alberta’s redeeming qualities all fit in a double D bra. She actually thought that Florida was between Los Angeles and New York.”
Jackson smiled and said, “Now, Misty, it may be more complicated than you think to get those big tits in those tiny lace bras.”
Misty laughed and said, “I still think that ‘Alberta Einstein’ is appropriate. She is coming to see you because she does not understand basic geography.”
I was not used to having discussions with a man who is naked and has a huge semi-hard cock. I kept trying to avoid staring at his cock. I think he may have noticed that I was looking at his long, thick cock. Misty did not seem to care that Jackson was showing her his cock.
Misty and Jackson talked business privately for 15 or 20 minutes and then Jackson rejoined me and the wine. He opened a new bottle and we talked for a while.
We talked about our workout routines, sports, women and investing. I told Jackson I was working 70 or 80 hour weeks in one of the Texas offices of the bank. He laughed and said, “I know you have to do that to get your opportunity to be a lead investment banker, but I do okay investing and work less than a couple of hours a day most of the time.”
I was stunned to hear that. I thought hedge fund managers worked constantly.
Jackson said, “Don’t tell anyone, but the way I invest, I make a few very hard decisions and then wait very patiently to see if we make money. I have found that I can be much more patient if my cock is in someone’s mouth or I am playing a sport. Staring at a computer screen is boring and makes me want to do something to relieve the boredom. I make more money when I am patient.”
It all sounded good to me.
Jackson showed me photos of the girl who was coming to visit him. The pictures were spectacularly sexy. Jenny had huge tits that appeared to be natural and was extremely skinny. She was blonde and beautiful. Jackson said that if I wanted, I could have sex with Jenny too.
Jackson said, “Jenny loves sex and she will fuck a good looking guy like you if I ask her nicely. Come to think of it, it would be fun if she fucked us both at the same time.”
I had never cheated on my wife and I wasn’t sure I wanted to start. However, my head was spinning from the fact that I was in a huge penthouse that must cost thousands per night with a guy I admired greatly drinking great wine. Now, I was being offered group sex with a beautiful lingerie model.
I knew I should say no, but instead, I said, “Why don’t we let Jenny decide.”
I figured that Jenny would only want to have sex with Jackson since she was flying across the country to see him.
Jackson said, “Great!”
We drank and talked some more. I was amazed at how open and unreserved Jackson was with me. It seemed like he would say most anything to me and was never embarrassed about it. He was extremely self confident and sure of himself. I guess that happens when you are tall, handsome, smart, rich and hung.
Late in the afternoon Jenny arrived at the penthouse. She was prettier in person than she was in the internet photos. Her face and hair were perfect, her body was fabulous and she was dressed in tight pants with sexy high heels. As advertized, her tits were almost too big to be real, yet they looked real and moved like real tits every time she took a step.
Jenny gave Jackson a kiss and shook my hand.
Jackson said, “Jenny, this is my friend, Joe. As you can see, he has a nice, muscular body. I thought it would be fun if Joe and I fucked you at the same time.”
I expected Jenny to object, but instead I heard, “Wow! That will be fun, Jackson. Do you want to do it here or the bedroom?”
“You two take your clothes off and head for the bedroom,” Jackson said.
So much for remaining faithful to my wife. I couldn’t believe this gorgeous girl was so willing to do whatever Jackson suggested, but I did not see how I could gracefully decline at that point and did not want to.
I pulled off my clothes and looked up to see Jenny release her giant tits. It was a spectacular sight to see her boobs bounce as she unhooked her sexy black lace bra. My cock was hard immediately.
Jackson said, “Jenny, look at that nice cock Joe has for you. It is big too. What is it Joe, 8 inches?”
“7 and a half,” I said.
Jenny said, “Man, this is going to be fun!”
I was relieved at her reaction because I was a little self-conscious about how much smaller my cock was than Jackson’s.
Jackson threw down his towel and revealed his cock that was longer and thicker than mine even though it wasn’t fully hard yet.
Jackson directed traffic in the bedroom. He had me lay on my back on the big bed in the middle. He positioned my body just the way he wanted by moving me around. Then, he had Jenny get in the 69 position on top of me. My cock was instantly in her mouth and it felt great. I started licking away at her pussy and squeezed her giant tits. The tits were definitely real.
Jackson provided encouragement to both Jenny and me. He was on his knees beside us as Jenny sucked my cock. Occasionally, Jackson would stick his big cock in Jenny’s face and she would suck it for a while before she came back to mine.
Jenny was moaning and squealing. Jackson was beside us talking dirty to Jenny and encouraging her to suck my dick harder and take it deeper.
Jenny could definitely suck a cock. I felt like I was on the verge of cumming in her pretty mouth. Jenny was obviously enjoying having her pussy licked.
Then, Jackson joined the activities in earnest. He came around behind Jenny on his knees. His big cock was hard and was just above my head as I licked Jenny. I was concentrating on Jenny’s lips on my cock when the head of Jackson’s huge cock appeared in front of my face and entered Jenny’s pussy. At first, only a little of Jackson’s cock was in her pussy, but Jenny was moaning and reacting to the big cock.
I had never been so close to a man’s cock. It was just an inch or two above my face. I was extremely turned on and started to lick Jenny’s clit even more enthusiastically. I was afraid I was going to lick Jackson’s cock and was afraid it might offend him.
I stopped licking for a moment and said, “Jackson, do you want me to move?”
Both Jackson and Jenny told me to keep licking Jenny’s pussy.
So, I had a close up view of a monster cock fucking a beautiful girl. Every time the giant cock would enter very far into Jenny, she would shudder and moan. I watched the cock go deeper and deeper into the pussy.
Finally, after a long while, Jackson rammed it all the way in. Jenny completely lost it and moaned loudly with my cock still in her mouth. I felt her cum as Jackson fucked her. I wanted to lick the big cock, but I was afraid of grossing out Jackson, so I just licked Jenny’s clit and from time to time felt Jackson’s big cock hit my face as he fucked Jenny.
I was so excited that a moment after Jenny started to orgasm, I exploded into Jenny’s mouth. Jackson continued to pound away at Jenny for a while and I think she came again.
Finally, Jackson buried his big cock deep into Jenny and came in her pussy. I was hard again from watching it happen right in front of me. For a few minutes, Jackson and Jenny had their weight on my face. Then, Jackson slowly pulled his cock out of Jenny and his big cock covered in cum and Jenny’s juices slowly slid across my forehead leaving a wet trail on my forehead and in my hair.
I had just cum, but I was totally horny and ready for more. I had never experienced anything nearly as hot as sex with Jenny and Jackson. Jackson smiled as he watched me wipe his cum off of my forehead.
I did not want to admit it even to myself, but I loved the idea of Jackson’s cock right in my face.
Jackson had dinner sent up to the suite and we all had dinner and more wine. After dinner, Jenny had to rush to catch her plane to New York. She gave us each a kiss and was gone.
Jackson and I continued to drink red wine and talk. Jackson had a way of getting people to talk about things they would never normally discuss. For example, he asked me what kind of porn I like to watch. For some reason, I told him I like porn involving girls giving blow jobs, submissive girls and dirty talking.
The next thing I know, he had me searching for this kind of porn on his laptop. Soon, Jackson was naked sitting next to me watching porn movies I had found. Jackson encouraged me to get naked too. I declined.
After a few more glasses of wine, Jackson started to rub his big cock as he watched the movies. I had never seen a guy beat off in front of me. I was embarrassed, but I was also fascinated by his enormous prick. It had to be 10 or 11 inches long and it was thick.
“Jackson, how long is that thing?” I asked.
“I don’t know.” he replied. “I will call Misty for a tape measure.”
I tried to discourage a call to Misty, but Jackson called immediately.
Misty appeared 15 minutes later with a tape measure.
Jackson said, “Joe wants to measure my cock. You may want to leave before he does it.”
I tried to protest, but Jackson was off to the rest room before I could correct him.
Misty asked, “Joe, are you bisexual?”
“No.” I said.
“Jackson is and he is very persuasive. You better watch out.” Misty warned.
I wasn’t sure I was completely against being persuaded and I was very interested to hear that Jackson was bisexual. But, to Misty I said, “Thanks for the warning. I will be careful, but it shouldn’t be too hard to resist since I am not gay.”
Misty just smiled and said, “Okay, but I used to say that I would never have sex with my boss before Jackson persuaded me to have sex with him. I didn’t even know I was being seduced.”
Misty left and Jackson came back with the tape measure. He said, “Joe, you want to help me get my cock hard before you measure it?”
I laughed and declined.
Jackson then handed me the tape measure and started jerking his cock. I was sitting next to him as he stroked his big cock. It seemed bigger than ever. I didn’t understand why, but I was excited to look at the big monster.
After a few minutes, Jackson told me to measure it. I tried to resist, but Jackson told me that just measuring his dick was not gay. So, I pulled out the tape and measured his hard cock.
It was truly magnificent. I had to touch it and sort of hold it as I measured. It was thick and heavy. I took my time with the measurement. I could feel Jackson staring at me as I touched his cock.
The measurement showed that Jackson’s cock was 11 inches long and was 7 inches around. I had to hold his cock in my hand for the measurement of the thickness. It was the first time I had ever touched a cock other than my own.
Jackson teased me about measuring it with my mouth, but I politely declined. I screwed up when I declined though because I said, “I am not ready for that!”
It was supposed to be a joke of some sort, but it sounded like I might be ready for it soon.
We kept drinking and talking. Jackson returned to the porn on his laptop. He asked, “Have you ever watched shemale porn, Joe?”
I said, “Yes.”
“Do you like it, Joe?”
“Yes, but I have never said that to anyone.”
Jackson said, “I won’t tell. Do you like the movies where the shemale has a big cock or the movies where the shemale has a little cock?”
I couldn’t believe I was having this conversation, but I was drunk enough to say, “I like the ones where the shemale has a huge cock.” I really did and I really did not know why. I was able to just compartmentalize it in my mind and not think about it very often.
Jackson looked me in the eye and said, “I bet you fantasize about sucking on a shemale’s huge cock.”
Without really thinking, I said, “Yeah, I have thought about that.”
I quickly blushed and tried to act like I didn’t really mean it, but I don’t think I was very convincing. I was sitting there thinking that I had just revealed something that I had not even admitted to myself to a guy I just met.
Jackson grabbed his dick and pointed it at me and said, “Would you like to suck mine?”
I said, “I don’t think so. I am not gay, man.”
Jackson smiled, gave me a long look right in my eye and said, “Okay, Joe.”
We talked, drank and watched porn including shemale porn. It was very late, so Jackson said we should go to bed.
As I walked toward the extra bedroom, Jackson said, “Hey, Joe, you want to sleep with me tonight in the master bedroom?”
I said, “I don’t think I am ready for that, Jackson. Thanks anyway.”
I spent the next ten minutes kicking myself for again suggesting that I was thinking about having sex with him. I felt like a dumbass, but I chalked it up to the wine and went to sleep.
I woke up on my side with Jackson’s big cock right in my face. It was hard again.
Jackson said, “I am sorry to wake you, but I was wondering if you would do me a big favor before your meeting today?”
“Sure, I will be glad to help you anyway I can.”
“Great! I woke up with this morning wood and I was hoping you would just help me out by beating me off. No sex or anything. You have already touched it, so it won’t be anything new.”
“I don’t know Jackson. I am not gay.”
“This isn’t gay,” he said, “It is just helping out a friend. I wouldn’t even ask if some woman I knew was around. It will be our secret; just between the two of us.”
I liked the idea of having a secret with Jackson. I looked at his handsome face and hard cock and said, “Okay, I will help you out, but don’t tell anyone.”
“I won’t!” Then, he jumped into bed beside me on his back and placed my hand on his big hard cock.
I started stroking his cock. Jackson had a big smile on his face as I stroked his cock. His right arm was sort of around me as I stroked his cock. I was completely turned on and my cock was hard. His cock was thick and heavy.
I was thinking that maybe Jackson would beat me off after I finished with him. It took longer than I expected given how hard he was when we started, but after a while, he began to breathe hard and soon shot a large amount of cum all over my hand and arm, his crotch and his stomach.
Jackson looked at my underwear and said, “Touching my dick made you hard.”
I blushed. I also jumped up to get him a towel. My hard cock was bouncing in front of me and making a tent in my boxers. I brought back the towel and cleaned up Jackson’s cum.
Jackson gently rubbed my cheek and chin with his hand and said, “Thanks, Joe. I owe you.”
He then ran his finger over my lips and lingered for a moment. Then, he hopped out of bed and went to take a shower.
I had company meetings that day. The retreat was supposed to include meetings the first day and last day with golf and other recreation in between. Jackson was scheduled to speak on the last day.
The weather did not look good for golf. It was looking like rain and I heard that a slow moving tropical depression was supposed to move in. I did not know what I would do if I could not play golf.
I went back to the penthouse for lunch at Jackson’s insistence. We had a pleasant lunch and talked investments. I really enjoyed it. At the end, Jackson asked me if I would play with his cock again. I told him that I would after my meetings.
As I left the penthouse, I ran into Misty who was coming to meet with Jackson. She said, “Hi, Joe. Are you still resisting my boss’ indecent proposals?”
I said, “Yes, but you were right about him being persuasive and persistent.” As I said “Yes,” I wondered if I was doing a very good job resisting when I had given Jackson a hand job and had promised another.
Misty smiled and said, “It will get harder. Just wait and see.”
I just laughed and headed toward the elevator.
At the afternoon meeting the president of the bank, Mr. Goldman, came up to me at a break and asked to speak privately to me. I had never met him and I was worried that I had done something wrong. I thought I was going to be fired.
When we were alone, Goldman said that he had received a call from Jackson Jennings and that Jennings had told him great things about me. He also said that Jackson wanted me to manage $25 million of Jackson’s cash for him and that more may be on the way. I was so low on the totem pole at the bank that I did not have authority to manage that much money, but Goldman told me that I had been given authorization.
“This is great, Joe. We have been trying to work with Jennings for years. You have managed to do it in a couple of days.”
Goldman shook my hand, congratulated me again and said, “Whatever you are doing, keep it up.”
I said, “I will do my best, sir!”
As I left Goldman, I thought about my hand on Jackson’s big, hard cock.
After my meetings, I went back to Jackson’s penthouse. Jackson was there in a perfectly tailored suit and a beautiful purple tie. He looked incredible. He met me with two big glasses of red wine.
I thanked him for picking me to manage some of his cash.
He said, “It is not very much money, but if you do a good job, I can send you some more.”
Twenty-five million seemed like a lot to me and this was huge for my career. I told him, “I will do whatever I need to do to take care of your money.”
“Just make a little more than zero percent and have it ready if I need it to invest.”
Jackson then went to a nearby counter in the kitchen and brought back two gift wrapped boxes. He gave me the boxes and said, “After you helped me out this morning, I told you I owed you. This is a little something I thought you might like.”
I did not know what to say. I was not used to receiving gifts from a guy I just met. I thanked him and began to open the gifts.
“Open the small one first,” Jackson suggested.
I did and I was blown away. It was a gold Patek Philippe watch. It was beautiful. I was no expert on expensive Swiss watches, but I knew that it cost tens of thousands of dollars.
I said, “Oh, my God! I can’t accept this. It is beautiful, but you shouldn’t spend this much money on a new friend. It is so thoughtful, but it is just too much.”
“Joe, don’t worry about it. I very much want you to have it. Please tell me you will keep it and wear it.”
“Are you sure?”
“I am sure.”
“Okay, thank you so much. Nobody has ever done anything so generous for me!”
“You are welcome. I am glad you like it.”
I put the watch on my wrist and admired it. I could not get over how cool it looked. I had not noticed before, but Jackson was wearing a similar Patek Philippe watch.
Jackson smiled and told me to open the other box. I tore off the paper and opened the box which appeared to be a box from an expensive women’s clothing store. I opened the box and saw four pairs of lace panties in various colors.
I was confused. “Are these for my wife?”
“No, Joe. They are for you. I think with your fit body they will look great on you.”
“Thanks, Jackson. They are very sexy, but I am not a crossdresser. I have never worn women’s underwear.”
Jackson looked at me right in the eye and said, “Joe, I did not think you were a crossdresser. I just admire your fit body and thought that you would look good in these panties. These are some sexy panties that I usually buy for women that I know, but I would love to see you in them. No one will know except for you and me. This will be another secret just between us.”
I thought about it for a minute and decided that it would not cause any harm and I wanted to repay Jackson for his kindness. So, I said, “What is your favorite color of panties?”
He smiled and said, “I would love to see you in the pink panties.”
I grabbed the box of panties and walked back to my bedroom. I did not understand it, but my cock was hard.
I had never had any desire to dress like a woman, but the idea of wearing panties because Jackson wanted me to wear them for him turned me on. It seemed forbidden or taboo. I was thinking about rubbing his cock while wearing very feminine lace panties and my cock was getting harder.
I took off all of my clothes and slipped on the thin lace panties. Wearing pink panties made me feel submissive and feminine. My hard cock stuck out of the top of the tiny little panties or created a big bulge in the panties if I pushed it to the side. Even though I had never really thought about wearing panties before and never thought I would, I had to admit that I looked pretty sexy in the panties.
I walked back in the living room wearing only the pink panties and my new watch. I could tell that Jackson loved how I looked. He had me spin around like a model.
I was embarrassed and aroused.
He said, “You look great in those lace panties. Your ass looks like a sexy girl’s ass.”
“Thank you.” I said with a big smile. While I said it, I was thinking how humiliating it was to be complimented on how nice my ass looked in pink panties. I could feel myself blushing.
He motioned for me to sit beside him on the couch. He had me sit right next to him. He handed me my wine and asked, “How does it feel to dress like that for me?”
“A little embarrassing and a little exciting, I guess.” I said.
“Do you feel feminine and submissive when you are wearing panties for me?”
“Yes, I have this sort of excited, feminine feeling like I want to be your girlfriend or something.” I regretted that statement as soon as I said it, but I just had a feeling that Jackson wanted me to say something like that after he gave me an expensive watch and these panties to wear for him.
“It is pretty easy to tell you are excited when your cock is popping out of your panties!”
I blushed again when he mentioned my hard cock and “my” panties.
I was about to ask Jackson if he wanted another hand job when he said, “Joe, will you do me another favor?”
I felt humiliated as I said, “Yes, anything you want.”
Jackson stood up from the couch and said, “Get on your knees, Joe.”
“Okay.” I said as I got on my knees in front of him. I could tell through his trousers that his cock was hard.
“Undo my belt and pants, Joe.”
I thought about being on my knees wearing panties as I unbuckled his pants and anxiously pulled his heavy cock out of his boxer shorts. He was hard. I was as excited as I have ever been.
I was once again facing this giant cock. It was inches from my face. He said, “I want you to be my cocksucker, Joe. I want you to be my girl.”
I knew I was going to do whatever he wanted. My cock was hard as a rock as I thought about being Jackson’s cocksucker.
I grabbed the base of his big hard cock and sheepishly kissed the head of his big cock. I looked up and saw his handsome face looking down and intently watching me kiss a cock for the first time.
I was trying to decide if I was going to swallow his cum as I licked the head of his cock and tasted a little precum. I felt so submissive to be servicing a man like this.
I timidly opened my mouth and slipped the head of the big dick into my mouth.
“Tell me what you are doing, Joe. I want to hear you say it.”
It embarrassed me to say it out loud, so I quietly said, “I will do what you want me to do, Jackson.”
“Tell me what you are doing,” Jackson repeated. “I want to hear you say it.”
I looked up at him and said hesitantly, “I am going to suck your cock.”
He smiled. “Start licking my balls and tell me you want to be my bitch.”
I lifted up his big cock and started licking his balls. I stopped for just a moment and said, “I want to be your bitch.”
He seemed satisfied with that and let me lick his balls for a while. I was very anxious to suck his big cock but, he clearly enjoyed having me lick his balls.
After a while, Jackson said, “Suck my cock, Joe.”
I stuck that big monster in my mouth and began to suck. I wanted to give him the best blow job he had ever received. To my surprise, giving a man head was not much different from having sex with a woman. I wanted to please my new lover and it made me very horny and excited.
Jackson’s cock was so big and so thick it filled my mouth completely. I loved it when a girl had deep throated my cock one time. I wanted to do that for Jackson. But, his cock was so big, I did not see how I could ever do it.
I do not have a strong gag reflex and I never get sick to my stomach, so I thought I would try my best. I began to focus on trying to take as much of his cock in my mouth as I possibly could. I sucked and I sucked and I kept trying to jam more and more cock in my mouth. My eyes were watering and from time to time I would gag. However, I kept trying.
Jackson seemed to love it. I was sucking his cock hard and I was getting something over half of it down my throat.
Jackson said to me, “Joe, you are a terrific cocksucker!”
When he said that to me, it made me feel good to get a compliment from him and it made me realize I was doing the nastiest thing I had ever done. I loved it.
My cock had been hard in my little pink panties since I put them on, but now I was so excited I could barely stand it. I started bobbing my head up and down on Jackson’s cock and for one of the first times in my life I came without touching my cock. My dick sticking out of the top of my new panties started shooting cum all over my stomach and legs and the floor. Some shot on Jackson’s shoes.
He laughed and said, “You are such a faggot, you came from sucking a dick.”
It made me even hornier to be called a faggot. Joe noticed that it excited me and he seemed to love the blow job. I never even slowed up when my cum was shooting everywhere.
Before long, I heard Jackson groan and he started cumming in my mouth. I did not have much choice about swallowing. The dick was so deep in my mouth cum just started shooting down my throat. I was surprised at how sweet his cum was and how good it tasted. Some of the cum filled my mouth and a little leaked out of my lips.
Jackson just said, “Man, that was awesome!” He pulled off his clothes and sat on the couch. He had me lay on the couch in just my pink panties with my head in his naked lap. He drank more wine while I nuzzled with his naked dick.
I kept my face in his naked crotch for about two hours as we talked and drank wine. My cock was hard again in no time. I had a close up view of Jackson’s cock getting hard again too.
We heard a knock at the door of the suite. Jackson said, “That must be Misty,” as he started to get up to go to the door.
I jumped up and ran toward my room saying, “Wait! She can’t see me like this!”
Jackson laughed as he said, “Who do you think bought those panties for you? Misty doesn’t care if you wear panties and suck cock.”
I felt totally embarrassed by the thought that Misty might know what we had been doing. I continued to run for my room. I slipped on a robe provided by the hotel.
Misty and Jackson talked business for a few minutes. Afterwards, Misty joined us in a glass of wine. Misty asked if I liked my new watch.
I said, “Yes, it is fantastic,” knowing that she must have bought the panties too. I was wracking my brain trying to think of a way to keep the fact that I was wearing panties for Jackson a secret. I couldn’t deal with the possibility that a beautiful woman would know that I had serviced a man.
However, the cat was soon out of the bag. Jackson said, “Hey Joe, show Misty those great looking panties you are wearing. They fit perfectly.”
I replied, “Panties, what panties?”
Jackson grinned and said, “We don’t keep secrets from Misty or she cannot do her job. Show her the panties.”
I knew I was busted. I could feel myself blush as I opened the robe and showed Misty the pink panties. I felt totally humiliated.
Misty was nice. “Those look so good on you Joe with your muscular body! That is the same brand Jackson used to buy for me before I got married. They are very sexy.”
Jackson said, “Joe, tell Misty your shoe size. We will have some more surprises for you soon.”
I told her, but I was still trying to get over the fact that I was wearing panties and everyone in the room knew it.
Misty left and we then had another glass of wine. I was mad that Jackson told Misty about the panties.
“Don’t worry about Misty. She won’t say a word to anyone about what goes on up here. Anyway, she already knew that I bought you the panties. It is not hard to figure that you would be wearing them.”
“I trust Misty too, but it is so embarrassing.” I said.
“She may see more embarrassing things before this week is over!”
When it was time for bed, Jackson asked me if I wanted to sleep with him. I thought about it for a minute and said, “I would love to.”
I assumed that when I said I would sleep with him that I was agreeing that he could fuck me with that giant cock. I was scared, but I wanted to do whatever he wanted.
Jackson slept naked and he wanted me to be in just my panties. I assumed that a dick would be up my ass for the first time before long.
However, Jackson had me suck his cock again and swallow his cum again. I think I managed to go a tiny bit deeper. I know I made him cum. I know that I came again in my panties just from the thrill of having his beautiful cock in my mouth. I slept like a baby.
I woke Jackson up with another blow job. His cum was like candy. I also was discovering that I loved to be called names while I sucked Jackson’s dick. It made me hard or harder every time he did it. He could tell I loved it.
While I had Jackson’s big dick in my mouth, he said, “Joe, you are a such a good cocksucker!”
Being called a cocksucker gave me this warm, submissive feeling and I moaned quietly. But, Jackson heard my moan and said, “Joe, you love to be complimented on your cocksucking, don’t you?”
“You love having a dick in your mouth, don’t you, Joe?”
“You are my new bitch, aren’t you, Joe?”
“Yes, Jackson.” I said as I moaned again.
This excited both of us and he soon filled my mouth with cum. I swallowed his cum and stayed in bed with Jackson for a while feeling like I did the first time I was in love.
We hung around the gigantic penthouse and had a nice breakfast. The rain was pouring and it was obvious that no golf would be played. We read the papers and checked emails and had a leisurely morning.
In the afternoon, Jackson suggested that we go down to work out and then get in the big indoor hot tub. I thought that sounded like fun, so we gathered our gear and headed to the gym. After a hard workout, Jackson and I rinsed off quickly in a shower and headed to the hot tub.
The hot tub was big and was next to a big indoor pool. The pool area had quite a few people from my bank hanging around drinking and swimming. I recognized quite a few people. The hot tub had 10 or so people in it, mostly women.
My boss’ wife, Carol, was in the hot tub talking to other middle aged women who looked familiar to me from various firm functions. A few of the women were attractive and looked good in their bathing suits. I said hi to Carol and her friends and introduced Jackson to them as we entered the hot bubbly water. It was interesting to watch these married women devour Jackson with their eyes as he entered the water.
Jackson was carrying on a conversation with the women and charming them as we gingerly entered the hot water. We took seats next to each other as Jackson continued to talk to the ladies. Several of them looked like they would fuck him in the hot tube if he asked.
I took my seat next to Jackson a normal distance from another man . Jackson casually grabbed my leg under the water and pulled me toward him. I tried to move closer without anyone noticing that I was sitting too close to another man.
I felt very self-conscious about sitting so close to Jackson in the hot tub. Our legs were touching and I would have never sat that close to a guy unless it was very crowded or something. But, I sat right where Jackson wanted me to sit.
Soon, under the water hidden by the bubbles, Jackson grabbed my hand and put it on his dick. My cock got hard as soon as I touched it. I could feel that big thick monster getting hard in my hand. I looked around the hot tub hoping that none of the women talking to Jackson could see what I was doing.
I kept rubbing the big cock and was getting more and more excited. My cock felt like it would bust out of my bathing suit.
Jackson casually leaned over to me and said, “Take my cock out.”
I didn’t know how to do that without it being obvious that I was playing with his crotch. I thought about it for a minute and then slid into the middle of the hot tub for a minute and when I returned to my seat I put my hand up the leg of Jackson’s swim suit and pulled his cock out of the leg of the suit. You need a big cock for that to work, but Jackson’s bare cock was now in my hand.
I loved it. I was jacking off Jackson’s hard cock under the water while he talked to a big group of women in the spa. I thought one woman looked at me a little funny, but I did not slow down.
I was really enjoying myself when Jackson turned to me and said, “Joe, I will buy drinks for us and all of these ladies if you will run over to that bar and find the waitress.”
I did not want to stand up out of the water with my hard cock sticking straight out. However, I felt like I couldn’t say no in front of these people. So, I let go of Jackson’s cock, tried to move my hard dick to the side and stood up.
I tried to move quickly, but I am afraid that several of the women saw my hard-on as I went to the bar. I found the waitress and we all started drinking. Jackson provided the entertainment for the entire hot tub. I provided Jackson with a hand job as he spoke to the group. His thick cock felt great in my hand.
After a few drinks, Jackson and I were sitting on the edge of the hot tub talking to the women. Jackson leaned over to me and whispered that he wanted me to go to one of the dressing rooms with him. I nodded yes.
We stood up together and Jackson directed me to one of the dressing rooms right off the pool area. The doors were visible from the hot tub and pool. I had a raging hard-on and I knew that Jackson’s cock was hard since it had been in my hand a minute or two before we stood up.
Jackson had his hand on the small of my back directing me. I felt like this was an action he would do with a girl he was escorting. It made me uncomfortable for all of my business associates and their wives to see me walking like this with Jackson. As we walked toward the dressing room, I knew that I would soon be sucking Jackson’s big gorgeous cock.
We walked to one of the doors to a dressing room and went inside. The room was very small. It was about the size of a changing room at a clothing store.
As soon as we closed the door, he said, “Suck my cock, Joe.”
I was worried about what everyone would think after seeing us walk into the little dressing room together. But Jackson said, “Pull out my cock and suck it, Joe.”
I got on my knees in front of him and pulled down his swim suit. His huge cock was only partially hard, but still almost hit me in the face. I started licking it.
I knew that it was obvious that something funny was going on when two men went into a small dressing room together, but I wanted Jackson’s cock so badly I did not care. I slipped the head of his hard cock into my mouth and began to suck.
I pulled my hard cock out of my bathing suit as I bobbed up and down on Jackson’s dick. I loved having his fat cock in my mouth. I was focusing on trying to take as much as possible down my throat.
As I sucked his cock, Jackson said, “You are becoming such a good cocksucker!”
I moaned as he called me a cocksucker. I felt my dick stiffen as he said it.
“You like being a cocksucker, don’t you, Joe?”
I tried to say yes, but with his big dick in my mouth, I could only mumble something that sounded vaguely like yes.
“You love being on your knees like a faggot, don’t you, Joe.”
I moaned again and tried to answer yes. I did not know until that moment how much I liked being called names as I sucked a cock. Of course, I was new to sucking cock. The humiliation of having a dick in my mouth as I was called degrading names was so exciting for me that I was on the verge of cumming every time he called me a nasty name.
“Tell me you are my cocksucking faggot.”
I pulled the dick out of my mouth and said, “I am your cocksucking faggot.”
“Tell me you will do anything for me.”
I pulled the dick out of my mouth again and said, “I will do anything for you, Jackson.” Then, I lost my head and said, “I love you Jackson!”
As the words left my mouth, I regretted them. I had just lost control for a second and let my inner most feelings out. Jackson gave me a funny look and rammed his big dick back in my mouth. I decided I didn’t care that I had just told a man that I loved him despite the fact I was married to a woman I loved. I sucked quicker and harder trying to please Jackson with my mouth.
“I am going to come all over your face, faggot”
I moaned again as he called me a faggot and I was pleased that I was about to make my man come. Then, his cock came out of my mouth and sprayed warm cum all over my face. I felt so feminine and submissive as I let him cum on me with his big beautiful cock.
I am not sure when, but sometime or another, I came all over the floor of the dressing room. I was so excited by this activity and being called names that I could not come close to controlling myself.
I started to wipe the cum off of my face when Jackson said, “Stop, Joe. I want you to go back to the hot tub with my cum on your face. People will know you are my bitch.”
I felt my cock twitch as he called me his bitch, but I could not go out to the pool area with cum on my face. I worked for these people. It would be humiliating.
“Please, Jackson,” I said, “I will do whatever you want, but don’t make me go out there with cum on my face.”
I was terrified that Jackson would make me talk to my business associates with his cum on my face. I felt like crying because I knew I would ultimately do what Jackson wanted. However, he must have realized how frightened I was because he gave me a break.
“Just swallow the cum off of your face in here,” he said. “You will feel like a whore licking up my cum.”
I eagerly started scooping his sperm into my mouth and eating it. I was so relieved and I loved his cum in my mouth. Jackson watched for a few minutes smiling and said, “You are such a little slut!”
With that, Jackson pulled up his swim suit and walked out of the dressing room. I pulled up my suit and tried to wipe up my cum on the floor and the remaining cum on my face with my hand.
I was worried that everyone at the pool knew or could guess that I had been sucking dick. I was afraid I would be fired or at least branded as a cocksucker for the rest of my banking career. The thought crossed my mind that maybe I would be protected by some law or company rule that prevented discrimination against gays. Then, I thought, “I am not gay! I am married!”
Then, it crossed my mind that some of my bosses would be pleased that I was sucking the dick of a billionaire. I knew I had to go face the music and just hoped for the best.
I took a deep breath and walked out the door hoping that I had eaten all of Jackson’s cum on my face and in my hair. As I did, I was relieved to see Jackson standing at the bar. I quickly walked over to join him hoping that nobody would notice me coming out of the dressing room.
“Joe, that was great!” said Jackson. “Here are our drinks. Head over to the hot tub and I will join you in a second.” He then answered a phone call on his cell phone.
I took a big drink of my cocktail and headed toward the hot tub full of company people. I saw all of the women who had been chatting with us. I then saw my boss’ wife. I was dying.
I quickly sat in the hot tub and tried to avoid eye contact. I felt humiliated as I got some funny looks from some of the women. The older, attractive woman who seemed so interested in Jackson was talking and laughing with my boss’ wife, Carol.
I sat there not talking to anyone for a few minutes when Carol said, “Joe, can we speak to you over here for just a second.
I didn’t want to go, but I didn’t want to make a scene by refusing to go. When I got near them, the older attractive woman said, “Joe, you have sperm on your face. After you go down on a guy, you need to look in the mirror before you go back in public.”
I said, “I didn’t go down on anyone!”
Carol laughed and said, “Joe, honey, you went in a dressing room with an attractive man and you came out with cum on your cheek and in your hair. It is pretty obvious what you have been doing. We were just trying to help you by letting you know you need to clean yourself up.”
I felt myself blush. “Thanks.” I said. “I appreciate the thought. Please, don’t tell anyone what you saw.”
Carol said, “We don’t care what you do in private, Joe. Does your wife know you are gay?”
“I am not gay!” I whispered.
“Okay, Joe.” Carol said. “Does your wife know you do things that cause you to have another man’s cum all over you?”
I couldn’t argue with that question and quietly said, “No, I didn’t know either until this trip.”
Carol smiled and said, “A handsome guy like that has caused a lot of people to get down on their knees.”
“Please don’t tell anyone, Carol.”
Carol looked around and said, “Joe, a lot of people probably saw you go into the dressing room with Jackson. It is probably too late.”
The other woman laughed and said, “Don’t worry, honey. My husband runs the bank and he wishes more guys would suck off rich hedge fund managers!”
I looked at her in shock and said, “Are you Mrs. Goldman?”
I closed my eyes and saw my career flying out of the window as I said, “Great. I may as well resign.”
“Don’t worry about it, Joe,” said Mrs. Goldman. “Lots of women have done a lot worse to get a big client.”
“I didn’t do it to get business!”
The women looked at each other and Mrs. Goldman said, “So, I guess you just like to be covered in cum?”
I closed my eyes again and didn’t know what to say.
Mrs. Goldman said, “It is okay, Joe. My husband will be thrilled that you are working on this relationship no matter why you are doing it.”
“Can you please keep it to yourself?”
“We’ll see.” Mrs. Goldman said. I was sure I was going to be fired.
About then, Jackson came over and told me that we needed to go back to his room. I practically ran out of the hot tub to join him.
“Did everyone notice that you sucked my cock, Joe?”
I laughed and said, “I don’t know, but the wives of my boss and the president of the entire bank noticed your cum on me.”
“Did it make you feel like a little slut to have people see you with my cum on your face? I bet you liked having those women know that you are my cocksucker.”
I hadn’t really thought of it that way and I did like the feeling I got when I thought about people knowing that I was sucking Jackson’s cock. I thought about it a second and said, “If I don’t get fired, I may like the idea of people finding out what I have been doing.”
“You won’t get fired as long as you are my special friend,” said Jackson.
He said it with such confidence, I believed it. I also knew myself well enough to know that I would not stop sucking his cock as long as he was offering it to me.
Jackson and I spent the rest of the day in our giant suite. We then had a nice dinner in one of the hotel restaurants. After dinner, we were drinking some more excellent red wine. I was never going to be satisfied with my $15 bottles I usually purchased back home again.
Jackson had me change into my white panties we sat on the couch with my head in his lap. Then, he said, “Joe, I have some more gifts for you.”
He took me to the kitchen table where a stack of gift wrapped boxes were located. He told me to open them and said, “These are really gifts for both of us. I can’t wait to see you in these!”
I opened the boxes and found 4 pairs of high heel women’s shoes in colors to match my new panties. I also was given thigh high stockings in colors that matched my new panties and high heels. All of the gifts were obviously expensive and in my size.
I have always liked women in thigh high stockings and high heels. I bought some for my sexy wife. Wearing panties was surprisingly fun and I was pretty sure that I would like the new gifts too.
Jackson said, “Misty has arranged for a woman from the hotel’s spa to come up and give you a shave. She should be here soon.”
I didn’t understand until Jackson told me that he thought I would look better with all of the hair below my waist shaved. I liked that idea, but I wondered how I would explain it to my wife.
A few minutes later, a young blonde woman came in and took me to the tub in the master suite to give me a complete shave. Jackson watched as she stripped me and shaved my pubic hair and legs. Then, Jackson suggested that she shave my entire body. I agreed, so the for the first time since puberty, my skin was smooth.
As soon as the spa woman left, I went to try on my new outfits. I picked the all white combination. I felt very sexy as I pulled on my new stockings. My cock looked great shaven.
Even I have to admit that I looked tall, slim and sexy in the high heels and stockings. My cock was hard as a rock. I came out of my room and modeled for Jackson. He loved the look.
It was hard to walk in the shoes, but the look was awesome. I was already pretty tall and thin, but in the very high heels, I looked like a high end call girl from the waist down. I noticed that Jackson’s cock was hard. I was unreasonably happy that I made his dick hard.
We had a glass of wine or two and I confessed to Jackson, “I thought when I agreed to sleep with you that you were going to fuck me in the ass. I was really relieved that you just wanted oral!”
Jackson looked a little surprised and said, “So, when you said you would sleep with me you were saying that you were ready to be fucked?”
“Yeah, I guess so.”
“Well, what are we waiting for? You look like you are ready to fuck and now I know you want my cock up your ass.”
He took me to the bedroom and had me get on all fours on the bed. I was afraid his big thick cock was going to rip me in half, but I loved the thought of Jackson being inside me. He used lots of lube and was surprisingly gentle at first.
I don’t know why I was afraid of anal sex, but I have always had a high pain threshold. The big cock hurt some, but I started to feel like it was a challenge like playing with pain in a football game. I took it like a man(or maybe like a woman).
As soon as Jackson knew that I could take it, he started driving that big dick deeper and deeper into me. I loved it. Even when it hurt, I loved it. I was being fucked for the first time. I started to moan and groan loudly.
Jackson said, “Joe, you are officially a faggot now that you are bent over and taking a cock up your sissy ass! Tell me you are a faggot!”
“I am a faggot!”
Cum started involuntarily coming out of my cock when he jammed his cock deep inside me. I felt like such a sissy with my ass up in the air and my head down on the bed. I felt like a whore and loved it!
“I am your whore, Jackson! Use me, baby!”
He started fucking me harder and harder and faster and faster. I was moaning so loud that people could probably hear me outside the suite.
After I had cum so much, I could not possibly cum anymore, Jackson moaned and filled my ass with cum.
He rolled off of me and asked me to gently lick his cock clean. I did not hesitate to take his cock into my mouth and lick it clean.
For the next day or so, the rain continued and I practiced being Jackson’s bitch. I hung around the suite almost all of the time and usually wore just panties, stockings and the high heels. I spent quite a bit of time trying to learn to walk in spike heels. It wasn’t easy, but I was learning. I came to think that I looked good in the high heels.
Jackson came and went during the day. But when he was around, I would frequently suck or fuck him. I became obsessed with his big cock. Occasionally, I would wonder what in the world I was doing, but I liked that cock so much that it was all I really wanted. I was avoiding calls from my wife.
On Friday morning, I quietly got out of bed and slipped on my matching pink outfit. I had on the heels, stockings and panties. In the living room of the suite, I bent over the back of the couch with my legs straight and looked at mirror. The bottom half of me looked like a sexy girl in pink lingerie. My cock was hard as a rock and sticking out of my pink panties.
I called out loudly for Jackson without changing positions. I called several times for him. Jackson walked out of the bedroom naked. His big cock was soft, but swinging between his legs.
I said, “Please fuck me, Jackson!”
He replied, “You look nasty, Joe. I would love to fuck you, but I have a meeting in a few minutes.”
“Fuck the meeting. You have time to fuck me! I will make you cum quickly!”
“Okay,” he said, “But I don’t think we have time for this.”
“Just give me that dick, man!”
I jumped down on my knees and started licking and sucking Jackson’s big cock. It was rapidly getting hard. I then started bobbing my head on his cock feeling like a submissive girl as I did.
After a few minutes of sucking, Jackson said, “Lie face down on the floor, Joe. I am going to pound your ass.”
I quickly went to the floor. I loved the anticipation as Jackson pulled down my panties and mounted me. I felt his hard cock between my cheeks as he climbed on top of me. Then, he raised up a little and slowly put his cock up my ass.
This was the first time we had tried this prone position. I felt like I was being impaled, but I was so horny, I loved it.
Jackson was clearly horny too. He normally took it slowly at first, but this time he just started pounding my ass.
I loved the sensation of my hard cock getting jammed into the floor by Jackson’s pounding.
“Tell me you are my whore, Joe!”
“I am your whore! Fuck me! Use me!”
I heard a sound near the door, but at most I figured it was Misty or the housekeeper. At that moment, I didn’t care if they saw me or heard me. In fact, it crossed my mind that it would be hot if lovely Misty saw this.
I moaned loudly and screamed, “I am your faggot Jackson! Fuck me harder with that big cock!”
About that time, I felt Jackson slow up and raise up a little. I looked up to see Misty standing in the room with Mr. and Mrs. Goldman. They looked shocked.
Jackson said to the Goldmans, “Sorry about this. How would it be if I meet you in the lobby in 15 minutes?”
I panicked and started wiggling around trying to get Jackson’s cock out of my ass so I could get up and run. After some struggle, Jackson figured out what I was trying to do and let me get up. However, getting up did not improve things. I was standing there in high heels and stockings with lace pink panties at my knees. My cock was embarrassingly hard and sticking straight out.
“Sorry Mr. Goldman! I did not know you were coming to visit. Let me go change and I will come to the meeting with Jackson.”
I reached down to pull up my panties so that I could try to run in the high heels to the bedroom. Mrs. Goldman was staring at the hard cocks on display and smiling.
Goldman looked at me like I was crazy and said, “Don’t bother coming to the meeting. I can’t keep an employee when I know he is having sex with a client. That is especially true when the client is as important as Mr. Jennings. I can’t look the other way when I have seen it in person. You will need to find another job, Joe.”