Making Partner Chapter 1
- 3 years ago
- 16
- 0
Making Partner - Chapter 2 free porn video
The cell phone that Jessica provided was ringing. It was 1am, and I wondered what I would be asked to do. I reached across my bed and picked up the phone. I swiped the green button and answered it.
"Hello, this is Stephen."
"My, oh my, you certainly were prompt in answering the phone, Stephen." It was Jessica, and she sounded like she was having fun with this little arrangement of ours already. "If you're worried about what kinky thing I want you to do to me, you can relax. I was just testing you to see if you would answer."
Jesus, I was nervous as hell when I picked up the phone. It was a relief to know that I wouldn't have to meet her somewhere in the middle of the night, although the prospect of running off to provide a sexual favor to Jessica wasn't really such a bad thing. "A test?" I asked.
"Yes, Stephen. I want you to know that I won't be testing you any more, since you passed the test with flying colors. But you must know that the next time I call you it will be the real thing. I might need someone to tuck me in, if you know what I mean."
"That won't be a problem, Jessica. I'll be ready and willing whenever you call."
"Very good. You can go back to bed now, my dear. I'll see you at the office tomorrow. Goodnight."
Before I could respond, the phone went dead. At least I answered it right away. Jessica seemed pleased that I showed that I would comply with her wishes. I rolled over and went right back to sleep.
The morning came much too quickly, and as I went through the shower and shave ritual I once again wondered if I had sold my soul to the devil. There were no guarantees that I would get the partnership, but having Jessica in my corner certainly gave me the inside track. I had no idea what kind of things she would have me do, either. If it were just straight sex with her it wouldn't be too bad, but somehow I had a nagging feeling that there might be other people involved. I mean, what would I do if she summoned me to her place, or any place, for that matter, and she wanted me to do a threesome? What if that threesome involved another man? It didn't do me any good at all to get worried about it, though. I had made the agreement with her, so anything she wanted me to do was fair game. I suppose the biggest fear I had was if I actually grew to like whatever she had in store for me. I've always considered myself to be pretty liberal when it came to sex. Now was my time to find out just how liberal I really am.
When I arrives at my office there were three e-mail messages waiting for me as soon as I booted up my computer. They were all from Molly. The first two were schedules of meetings that Jessica had set up for me that would prepare me for some cases she had assigned to me. The third one was interesting. Jessica wanted me to meet with her at 11:30 am in her office. At her request, I was not to bring anything to the meeting. No briefcase, no folders, nothing. Jessica had everything I needed for this meeting.
Well, that really piqued my interest. I wondered if this was a working meeting or maybe a "special" meeting. I guess I would find out when I got there.
I breezed through the two case meetings that Jessica had assigned to me. They were fairly simple cases, but they involved two of our biggest clients. They didn't seem surprised or upset at all that Jessica had assigned their cases to an associate. Clients of this magnitude usually demanded that a partner either handle every aspect of the case or work in tandem with an associate. The fact that Jessica trusted me enough to go solo on these two cases must have been good enough for them. Of course, it didn't hurt matters that, during both meetings, I showed both clients that I had a thorough understanding of their cases and was well-versed in the particular laws which applied to their cases. Both clients seemed quite pleased at the way I not only conducted myself, but also with the way I outlined what our position was and how to proceed with the case to give them a favorable ruling.
When I got to Jessica's office suite for the 11:30 meeting, Molly was there at her desk. She was wearing what I could only call a finely tailored suit that would have looked good on a man. Still, Molly exuded a sexuality about her that intrigued me. If I could only crack that hard veneer she had going for her, I might discover more about the real Molly.
"Mr. Kramer, " Molly announced in that husky voice of hers, "Jessica will see you now."
As I walked past Molly I caught her looking at me. Actually, it was more like she was ogling me. She had looked me up and down, as if she were checking out something she liked. Then again, maybe it was wishful thinking on my part. Regardless, I gave her my best smile as I passed.
I was still smiling as I entered Jessica's office.
"My, you seem awfully happy," said Jessica. "After my test call last night I expected you to be a little more fatigued."
"Jessica, I think that as you get to know me you'll find that I have a lot of staying power."
Jessica smiled at my last remark. "Well, Stephen, I got rave reviews from those clients you met with earlier today. They were very impressed with everything about you. That's a good start for you, because making our heaviest hitters happy isn't easy for even the best litigators we have here."
"Thank you, Jessica. I was well prepared, thanks to the informational packet you prepared for me."
"You just keep up that kind of work and your path to the partner position will be smooth and easy. Stephen, I've got an assignment for you. This one isn't work-related, at least it doesn't require your legal expertise."
"What do you need, Jessica?"
"There is a friend of mine who is going to need an escort to a book signing tonight. I want you to make sure that she has a good evening. And by a good evening, I mean that her every need will be taken care of. Do you understand what I'm saying?"
"Yes, I think I do."
"Molly will give you the details on what you need to know. You'll be expected to impress my friend in every way possible, so please don't disappoint her...or me."
"You can count on me, Jessica."
Outside Jessica's office, Molly was waiting for me. She had a manila envelope that she handed to me. "Mr. Kramer, I think the information in this envelope is pretty much self-explanatory, but it is important that you are dressed and ready at 6:30 sharp. A limo will be at your place to pick you up. Jessica's friend will be inside waiting for you. You do own a tux, don't you?"
"Yes, I do, Molly. Is there anything else you can tell me about this woman? Her likes, dislikes? Anything that isn't included in your report that might give me some additional insight?"
Molly actually smiled at me, the first time I've seen anything other than a serious look on her face. "I shouldn't be telling you this, but Jessica's friend likes to be in charge of everything. And I mean everything. Keep that in mind and you'll make her very happy."
"Thank you, Molly." I wondered how Molly came to know that little tidbit about this woman. Maybe someday I would find out.
Upon returning to my office, I opened the envelope. There wasn't a whole lot of information on the woman I would be escorting tonight.
Her name was Helena Rogers. She was 56 and had never been married, She made her fortune in real estate and preferred the literary scene, as she was something of a silent benefactor to up and coming writers, one of whom was being honored with the book signing tonight. There was no photo of her, so I wouldn't know what she looked like until I got into the limo.
At 6:30 sharp, the limo arrived. The driver got out and opened the rear door for me. As I climbed inside, I was shocked at what I saw.
Helena was stunning in her beauty. Tanned, slender and beautiful, she wore her raven black hair pulled back tightly into a short ponytail. Her black evening gown probably cost the equivalent of a year's salary for me. She had an exquisite strand of pearls around her neck and had two rings on her fingers. Her makeup appeared to be professionally applied.
"Good evening, Mr. Kramer. It's so nice to make your acquaintance. Would it be okay if I called you Stephen?" Her accent was refined British.
"Stephen is just fine, Ms. Rogers."
"Oh, please, Stephen. Call me Helena. Jessica speaks well about you, Stephen. I'm hoping that you are everything she says you are."
"Well, thank you Helena. I'll try hard to live up to your expectations."
We were driven to a bookstore on a side street of the downtown area. It didn't look like much, judging by the exterior, but once we went inside it was quite different. It reeked of money, both by the décor as well as the collector's editions of some of the books on display. There were waiters and waitresses milling about, with Hors d'oeurvres and drinks on the trays they were carrying.
Helena was on my arm the entire time we were at the bookstore, stopping to introduce me as "one of my attorneys" to several of her friends. One of them, a very attractive woman named Amelia, lingered around us longer than anyone else. Amelia could have passed for an Amazon, as she stood around 6 feet tall. Everything about Amelia was a little on the large side, from her enormous breasts to her cushiony ass. Even her hands were large. Helena waited until Amelia was out of earshot and then revealed a little of what was to come.
"Stephen, darling, what do you think of Amelia? Isn't she just the sweetest thing you've ever seen?"
"She's a little on the plus side," I replied. "But she's definitely put together, if that's what you mean."
"Oh, Stephen," Helena giggled. "Of course that's what I mean. Amelia is going to go back to my place with us when this little soiree is over. I think you'll like what she brings to the table. She can suck your dick so well, you'll think it was caught in a vacuum cleaner."
So Helena was into the threesome scene, I thought. And we were going to be making it with Amelia. I knew that sooner or later I would be getting into some kinky shit with Jessica or her friends, so I guess we might as well start out big.
As the evening wore on, Helena introduced me to a wide variety of people. Most of them were wealthy, I thought, because of the way they were dressed, the way they spoke and because they all seemed to carry themselves with an air of superiority. I was pretty much bored with the lot of them, but I was here to please Helena so I went along with everything.
Finally we met the author. Talk about someone who was out of place! This guy appeared to be the most down to earth person in the room. He was intelligent, soft-spoken and was genuinely friendly to everyone he met. I had to assume that he had been one of the authors who Helena had bankrolled. Perhaps there were others at the party who had given him financial support as well. That had to be the only reason he was putting up with most of them.
Once that was over, Helena told me that we were done here and we should get back to her place. She pigeonholed Amelia and whispered something in her ear. Amelia smiled and then looked at me, licking her lips as she did.
The three of us got into the waiting limo and the driver took us to Helena's place, a high-rise on the East side of the city. Once inside the private elevator, Helena and Amelia began to kiss, wet sloppy kisses with lots of tongue action. I just stood there watching.
The elevator stopped on the top floor and the doors opened into Helena's penthouse suite. Her apartment was both huge and very tastefully decorated. We wasted no time at all and headed straight for a large bedroom.
"Stephen," Helena said. "Why don't you get undressed? Amelia and I will get started while you do that.
Helena unzipped her gown and let it fall to the floor, revealing smallish breasts with huge nipples. Her pussy was accented by a thin strip of hair right above it. Otherwise, she was clean shaven. Amelia removed her top and was sporting a huge set of tits, with large nipples to match.
Helena ordered me to lay down on the bed, flat on my back. She then proceeded to take my semi-erect cock into her mouth. She was good at sucking cock, licking the head and up and down the shaft. I was hard in no time at all.
Once I was hard, she took my dick in her hand and called out to Amelia. "Amelia, honey, you've simply got to get a taste of this. Get over here, bitch!"
Amelia came over with her mouth open and proceeded to take my entire length down her throat. Helena was right about the vacuum cleaner. Amelia was applying powerful suction to my cock as her tongue swirled around the head. She was good, if a little aggressive.
Helena returned with a blindfold. "Here, Stephen, put this on. You won't believe how the lack of sight enhances sex." She then pushed Amelia out of the way.
I did as I was told and slipped the blindfold over my eyes. Helena had resumed sucking me and was using her hands to pump my shaft up and down as she ate my cock.
After a few minutes of sucking my prick, I heard Helena say something to Amelia.
"Get over here, Amelia. I want you to fuck me with that big thing while I fuck Stephen."
Now things were really getting weird. Helena mounted my cock and began to work her way up and down on me. One thing about her, she was tight! Her pussy gripped my cock like it would never let go. Helena shifted herself and leaned forward on me, giving me kisses as she fucked me. Helena was right about not being able to see. The sensations were incredible and I could only imagine what she must have looked like as she slid up and down on my bone.
Amelia must have been using a strap-on, because suddenly Helena began to gasp and moan as her ass was violated. I could feel Amelia's legs against mine as she fucked Helena. This was getting very strange, but my mission was clear. Helena's pleasure was job one, and I would have done anything at that point to make her cum.
"Oh, God," Helena gasped. "I've got you both inside me and I'm loving this!. Stephen, you have got to let Amelia do you. She is incredible! Oh, dear God, I'm cumming! Arghh, umph!"
I could feel Helena's juices flow down around my cock and onto my thighs. Amelia was still pounding Helena's ass with the strap-on. She was not able to cum for real, but she was giving Helena a real show the way she was moaning herself.
Helena collapsed atop me. "That's all I can take, big boy. It's your turn next." She got off me and rolled me over. Taking a bottle of lube from the nightstand, she proceeded to grease up my asshole for the anal invasion that was to come.
I've had women use butt plugs on me before, but never anything too large. From the sounds of it, Amelia was using something a lot larger than anything I've been accustomed to.
"Get up on all fours," said Helena. "Stephen, you're gonna love this!" Helena was working her fingers in and out of my ass, helping to prepare me for Amelia's tool. I've got to admit, I was really getting turned on by Helena's fingers. She massaged me until my sphincter loosened and then shoved three fingers deep inside my ass. The sensation was unlike anything I had ever felt. Just as I was getting to really like what she was doing, she withdrew her fingers. "Okay, baby, he's all yours."
Not being able to see anything made each sensation seem exaggerated, but it only intensified the pleasure. I could feel the tip of Amelia's strap-on easing against my asshole. She must have had one hell of a strap-on, because it was warm and very soft, very lifelike, yet still hard where it needed to be. I took a deep breath as she slid the head of it into my ass. God, this was driving me crazy.
Helena had positioned herself underneath me, so that she was able to kiss me and offer her tits to my open mouth. I sucked greedily on her long, hard nipples as Amelia slowly fed me her "dick". Did I mention that it must have been one hell of a strap-on? This thing had the feel of the real thing, warm, wet and throbbing.
As I sucked on Helena's exquisite boobs, Amelia had buried herself inside my hot and tight ass. She began thrusting this thing in and out of me, panting as she increased the tempo. I was stuffed beyond belief, and yet the sensations were strangely delicious. I was enjoying my first ass fucking with a dildo, believe it or not.
Helena began to stroke my cock as Amelia continued fucking me. I was sure that I wouldn't last long, as both of these women were exciting every nerve ending in my body.
Amelia was moaning now. "Stephen, you feel so good, so good and tight. I'm almost ready to cum, baby!"
Huh? Feel so good and tight? Wow, she must have a rabbit attached to that thing if she was getting off. I know that I was about to give Helena a handful of hot cum any second now. The combination of being ass fucked along with Helena's expert hands was pushing me over the edge. Any minute now...
Just then Amelia screamed. "Oh dear God, I'm gonna cum! Take my cum, Stephen!"
The next several seconds was confusing, but Amelia had pulled out of my ass and flipped me onto my back. Her strength was amazing, as she tossed me on my back as if I were a mannequin.
As I lay there, my orgasm on hold, Helena ripped the blindfold off my face. There, staring me in the face, was Amelia. She had straddled my chest and was thrusting a wet, throbbing cock into my face. Wait a minute, I thought. Then it hit me.
A COCK!! It was a real, live COCK!! As I became aware of what was going on, Amelia pointed it at my gaping mouth and began to shoot streams of cum at me. Some of it went into my open mouth, some went all over my face and still more of it landed in my hair and onto the bed. I was gagging and spurting as the hot, sticky fluid went down my throat and I involuntarily swallowed. Amelia began to rub her cock all over my face, smearing her cum all over me. Helena was licking it off my face and gulping down what she could.
Then Amelia rubbed her huge cock on my lips. I tried to resist what she was doing, which was forcing my mouth open so that I could suck her clean, but then Helena spoke to me in a peaceful, calming voice.
"Go ahead and take it, Stephen. It's what I want. Believe me, you'll love it as much as I do."
I was repulsed by the thought of sucking this tranny's cock, but I had to think about the big picture. Reluctantly, I opened my mouth and took her cock. It was covered in cum and still semi-hard. I licked the cum away and even began to suck on it. Strangely, after the first few seconds the revulsion went away, replaced by an odd desire to suck her cock clean. I found myself becoming hard again, and Helena squeezed my cock as if she were milking a cow. Gulping down Amelia's cum and my own ass juices seemed to turn me on and, with Helena's aid, I found myself ready to cum.
Amelia pulled her cock from my mouth and positioned herself alongside Helena. As my cock began spurting my seed, the two of them took turns sucking my dick and receiving the hot jets of my cum. They licked it, licked each other and gulped down my essence. When I finished spraying them with my cum, they fell back on the bed. Amelia pulled me down so that we could lie there together.
What a sight it must have been, the three of us lying together on the bed, our faces caked with the dry residue of mine and Amelia's cum. Helena broke the silence first.
"Stephen, I apologize for deceiving you, and for using the blindfold, but you surely would have balked if you knew about Amelia from the beginning. You'll have to admit, though, that it was unlike anything you've ever done. Be honest with me now, did you enjoy yourself?"
"Strangely enough, Helena, I did. I must have been something to see when Amelia stuck her cock in my face, but once I took her into my mouth it was as arousing as anything I have ever done. Amelia, you were wonderful tonight. You got two of my cherries in one evening."
Amelia laughed at that one. "You know, Stephen, you were a good sport about it. It's not often that Helena and I are able to find a willing partner, but you have been the best one so far. Would you be willing to try it again sometime?"
"I might , Amelia, I just might. You've opened the door to some interesting things tonight. I wouldn't mind getting inside that beautiful ass of yours someday, that's for sure."
"Then I'll have to set something up for another day," said Helena. "I'm much too tired after all of this tonight, but I promise we'll get together real soon. Amelia, what do you say we get our boy toy cleaned and dressed? I'm sure that he could use some sleep after giving two women such a wonderful time."
The two of them led me to the bathroom. Helena had a massive walk-in shower, with shower heads on three sides. They led me in and we washed each other until we were sparkling clean. I found myself getting aroused again when Amelia had me wash her huge cock. It was still a little strange, running my hands along the shaft of another cock, but it was very erotic, and opened my mind to many new possibilities for the future.
After we dried ourselves and got me dressed, the two ladies gave me goodnight kisses. They never did get dressed, and I assumed that they were going to spend the night here in Helena's bed.
Walking me to the elevator door, Helena had some parting words for me.
"Stephen, I can't thank you enough for a wild and wonderful evening. I'll be sure to tell Jessica that you went above and beyond my expectations tonight. I'll leave out some of the kinkier details, but I'm sure she will be pleased. The driver will take you back home as soon as you reach the ground floor. You have a good night, Stephen. Don't forget about our offer of doing this again. We'd love to see where we can take you with more time on our hands." She then took my head in her hands and gave me a sweet, tender kiss.
"Thank you for everything, Helena," I said. "I really enjoyed myself, once I let my inhibitions go. I'll keep your offer in mind. Get in touch with me when you want to do part two." I handed her one of my business cards. I was serious about getting together with them again.
Once I got back to my place I took stock of the evening. Once things got hot back in Helena's apartment I began to really enjoy myself, despite my original displeasure at being with a transsexual. All in all, things turned out pretty well.
Sleep came quickly, as the two women had really worn me out.
The next morning I arrived at the firm and began going over my schedule for the day as I had a large cup of coffee. As I went over my schedule, mail arrived from Molly. Jessica requested my presence at 11:30 again. I wondered if this was going to be her modus operandi, calling me in to tell me that she had a friend in need of servicing. Oh well, I thought, this is what I signed up for. That little bit of rationalization was what kept me from thinking of myself as Jessica's male whore. The problem was, I was already beginning to enjoy my role.
I walked into Jessica's suite and there sat Molly. She had on a yellow floral top and a flowing white pleated skirt. I smiled as I saw her outfit. She was looking more feminine this morning, a far cry from the austere, masculine look I had always seen her in.
"Good morning, Molly," I said to her. "You're looking quite attractive in that outfit."
Molly just looked at me, no expression at all on her face, as usual. "How was your assignment last night, Mr. Kramer? Did you get a chance to meet Amelia?" This time she showed me a slightly wicked smile, like she knew all about what I was into last night. "She's something else, isn't she?" Now she had a huge smile on her face and I detected a little blushing going on.
I just smiled and winked at her as I went by to enter Jessica's office. One of these days, I thought to myself. One of these days...
"Hello, this is Stephen."
"My, oh my, you certainly were prompt in answering the phone, Stephen." It was Jessica, and she sounded like she was having fun with this little arrangement of ours already. "If you're worried about what kinky thing I want you to do to me, you can relax. I was just testing you to see if you would answer."
Jesus, I was nervous as hell when I picked up the phone. It was a relief to know that I wouldn't have to meet her somewhere in the middle of the night, although the prospect of running off to provide a sexual favor to Jessica wasn't really such a bad thing. "A test?" I asked.
"Yes, Stephen. I want you to know that I won't be testing you any more, since you passed the test with flying colors. But you must know that the next time I call you it will be the real thing. I might need someone to tuck me in, if you know what I mean."
"That won't be a problem, Jessica. I'll be ready and willing whenever you call."
"Very good. You can go back to bed now, my dear. I'll see you at the office tomorrow. Goodnight."
Before I could respond, the phone went dead. At least I answered it right away. Jessica seemed pleased that I showed that I would comply with her wishes. I rolled over and went right back to sleep.
The morning came much too quickly, and as I went through the shower and shave ritual I once again wondered if I had sold my soul to the devil. There were no guarantees that I would get the partnership, but having Jessica in my corner certainly gave me the inside track. I had no idea what kind of things she would have me do, either. If it were just straight sex with her it wouldn't be too bad, but somehow I had a nagging feeling that there might be other people involved. I mean, what would I do if she summoned me to her place, or any place, for that matter, and she wanted me to do a threesome? What if that threesome involved another man? It didn't do me any good at all to get worried about it, though. I had made the agreement with her, so anything she wanted me to do was fair game. I suppose the biggest fear I had was if I actually grew to like whatever she had in store for me. I've always considered myself to be pretty liberal when it came to sex. Now was my time to find out just how liberal I really am.
When I arrives at my office there were three e-mail messages waiting for me as soon as I booted up my computer. They were all from Molly. The first two were schedules of meetings that Jessica had set up for me that would prepare me for some cases she had assigned to me. The third one was interesting. Jessica wanted me to meet with her at 11:30 am in her office. At her request, I was not to bring anything to the meeting. No briefcase, no folders, nothing. Jessica had everything I needed for this meeting.
Well, that really piqued my interest. I wondered if this was a working meeting or maybe a "special" meeting. I guess I would find out when I got there.
I breezed through the two case meetings that Jessica had assigned to me. They were fairly simple cases, but they involved two of our biggest clients. They didn't seem surprised or upset at all that Jessica had assigned their cases to an associate. Clients of this magnitude usually demanded that a partner either handle every aspect of the case or work in tandem with an associate. The fact that Jessica trusted me enough to go solo on these two cases must have been good enough for them. Of course, it didn't hurt matters that, during both meetings, I showed both clients that I had a thorough understanding of their cases and was well-versed in the particular laws which applied to their cases. Both clients seemed quite pleased at the way I not only conducted myself, but also with the way I outlined what our position was and how to proceed with the case to give them a favorable ruling.
When I got to Jessica's office suite for the 11:30 meeting, Molly was there at her desk. She was wearing what I could only call a finely tailored suit that would have looked good on a man. Still, Molly exuded a sexuality about her that intrigued me. If I could only crack that hard veneer she had going for her, I might discover more about the real Molly.
"Mr. Kramer, " Molly announced in that husky voice of hers, "Jessica will see you now."
As I walked past Molly I caught her looking at me. Actually, it was more like she was ogling me. She had looked me up and down, as if she were checking out something she liked. Then again, maybe it was wishful thinking on my part. Regardless, I gave her my best smile as I passed.
I was still smiling as I entered Jessica's office.
"My, you seem awfully happy," said Jessica. "After my test call last night I expected you to be a little more fatigued."
"Jessica, I think that as you get to know me you'll find that I have a lot of staying power."
Jessica smiled at my last remark. "Well, Stephen, I got rave reviews from those clients you met with earlier today. They were very impressed with everything about you. That's a good start for you, because making our heaviest hitters happy isn't easy for even the best litigators we have here."
"Thank you, Jessica. I was well prepared, thanks to the informational packet you prepared for me."
"You just keep up that kind of work and your path to the partner position will be smooth and easy. Stephen, I've got an assignment for you. This one isn't work-related, at least it doesn't require your legal expertise."
"What do you need, Jessica?"
"There is a friend of mine who is going to need an escort to a book signing tonight. I want you to make sure that she has a good evening. And by a good evening, I mean that her every need will be taken care of. Do you understand what I'm saying?"
"Yes, I think I do."
"Molly will give you the details on what you need to know. You'll be expected to impress my friend in every way possible, so please don't disappoint her...or me."
"You can count on me, Jessica."
Outside Jessica's office, Molly was waiting for me. She had a manila envelope that she handed to me. "Mr. Kramer, I think the information in this envelope is pretty much self-explanatory, but it is important that you are dressed and ready at 6:30 sharp. A limo will be at your place to pick you up. Jessica's friend will be inside waiting for you. You do own a tux, don't you?"
"Yes, I do, Molly. Is there anything else you can tell me about this woman? Her likes, dislikes? Anything that isn't included in your report that might give me some additional insight?"
Molly actually smiled at me, the first time I've seen anything other than a serious look on her face. "I shouldn't be telling you this, but Jessica's friend likes to be in charge of everything. And I mean everything. Keep that in mind and you'll make her very happy."
"Thank you, Molly." I wondered how Molly came to know that little tidbit about this woman. Maybe someday I would find out.
Upon returning to my office, I opened the envelope. There wasn't a whole lot of information on the woman I would be escorting tonight.
Her name was Helena Rogers. She was 56 and had never been married, She made her fortune in real estate and preferred the literary scene, as she was something of a silent benefactor to up and coming writers, one of whom was being honored with the book signing tonight. There was no photo of her, so I wouldn't know what she looked like until I got into the limo.
At 6:30 sharp, the limo arrived. The driver got out and opened the rear door for me. As I climbed inside, I was shocked at what I saw.
Helena was stunning in her beauty. Tanned, slender and beautiful, she wore her raven black hair pulled back tightly into a short ponytail. Her black evening gown probably cost the equivalent of a year's salary for me. She had an exquisite strand of pearls around her neck and had two rings on her fingers. Her makeup appeared to be professionally applied.
"Good evening, Mr. Kramer. It's so nice to make your acquaintance. Would it be okay if I called you Stephen?" Her accent was refined British.
"Stephen is just fine, Ms. Rogers."
"Oh, please, Stephen. Call me Helena. Jessica speaks well about you, Stephen. I'm hoping that you are everything she says you are."
"Well, thank you Helena. I'll try hard to live up to your expectations."
We were driven to a bookstore on a side street of the downtown area. It didn't look like much, judging by the exterior, but once we went inside it was quite different. It reeked of money, both by the décor as well as the collector's editions of some of the books on display. There were waiters and waitresses milling about, with Hors d'oeurvres and drinks on the trays they were carrying.
Helena was on my arm the entire time we were at the bookstore, stopping to introduce me as "one of my attorneys" to several of her friends. One of them, a very attractive woman named Amelia, lingered around us longer than anyone else. Amelia could have passed for an Amazon, as she stood around 6 feet tall. Everything about Amelia was a little on the large side, from her enormous breasts to her cushiony ass. Even her hands were large. Helena waited until Amelia was out of earshot and then revealed a little of what was to come.
"Stephen, darling, what do you think of Amelia? Isn't she just the sweetest thing you've ever seen?"
"She's a little on the plus side," I replied. "But she's definitely put together, if that's what you mean."
"Oh, Stephen," Helena giggled. "Of course that's what I mean. Amelia is going to go back to my place with us when this little soiree is over. I think you'll like what she brings to the table. She can suck your dick so well, you'll think it was caught in a vacuum cleaner."
So Helena was into the threesome scene, I thought. And we were going to be making it with Amelia. I knew that sooner or later I would be getting into some kinky shit with Jessica or her friends, so I guess we might as well start out big.
As the evening wore on, Helena introduced me to a wide variety of people. Most of them were wealthy, I thought, because of the way they were dressed, the way they spoke and because they all seemed to carry themselves with an air of superiority. I was pretty much bored with the lot of them, but I was here to please Helena so I went along with everything.
Finally we met the author. Talk about someone who was out of place! This guy appeared to be the most down to earth person in the room. He was intelligent, soft-spoken and was genuinely friendly to everyone he met. I had to assume that he had been one of the authors who Helena had bankrolled. Perhaps there were others at the party who had given him financial support as well. That had to be the only reason he was putting up with most of them.
Once that was over, Helena told me that we were done here and we should get back to her place. She pigeonholed Amelia and whispered something in her ear. Amelia smiled and then looked at me, licking her lips as she did.
The three of us got into the waiting limo and the driver took us to Helena's place, a high-rise on the East side of the city. Once inside the private elevator, Helena and Amelia began to kiss, wet sloppy kisses with lots of tongue action. I just stood there watching.
The elevator stopped on the top floor and the doors opened into Helena's penthouse suite. Her apartment was both huge and very tastefully decorated. We wasted no time at all and headed straight for a large bedroom.
"Stephen," Helena said. "Why don't you get undressed? Amelia and I will get started while you do that.
Helena unzipped her gown and let it fall to the floor, revealing smallish breasts with huge nipples. Her pussy was accented by a thin strip of hair right above it. Otherwise, she was clean shaven. Amelia removed her top and was sporting a huge set of tits, with large nipples to match.
Helena ordered me to lay down on the bed, flat on my back. She then proceeded to take my semi-erect cock into her mouth. She was good at sucking cock, licking the head and up and down the shaft. I was hard in no time at all.
Once I was hard, she took my dick in her hand and called out to Amelia. "Amelia, honey, you've simply got to get a taste of this. Get over here, bitch!"
Amelia came over with her mouth open and proceeded to take my entire length down her throat. Helena was right about the vacuum cleaner. Amelia was applying powerful suction to my cock as her tongue swirled around the head. She was good, if a little aggressive.
Helena returned with a blindfold. "Here, Stephen, put this on. You won't believe how the lack of sight enhances sex." She then pushed Amelia out of the way.
I did as I was told and slipped the blindfold over my eyes. Helena had resumed sucking me and was using her hands to pump my shaft up and down as she ate my cock.
After a few minutes of sucking my prick, I heard Helena say something to Amelia.
"Get over here, Amelia. I want you to fuck me with that big thing while I fuck Stephen."
Now things were really getting weird. Helena mounted my cock and began to work her way up and down on me. One thing about her, she was tight! Her pussy gripped my cock like it would never let go. Helena shifted herself and leaned forward on me, giving me kisses as she fucked me. Helena was right about not being able to see. The sensations were incredible and I could only imagine what she must have looked like as she slid up and down on my bone.
Amelia must have been using a strap-on, because suddenly Helena began to gasp and moan as her ass was violated. I could feel Amelia's legs against mine as she fucked Helena. This was getting very strange, but my mission was clear. Helena's pleasure was job one, and I would have done anything at that point to make her cum.
"Oh, God," Helena gasped. "I've got you both inside me and I'm loving this!. Stephen, you have got to let Amelia do you. She is incredible! Oh, dear God, I'm cumming! Arghh, umph!"
I could feel Helena's juices flow down around my cock and onto my thighs. Amelia was still pounding Helena's ass with the strap-on. She was not able to cum for real, but she was giving Helena a real show the way she was moaning herself.
Helena collapsed atop me. "That's all I can take, big boy. It's your turn next." She got off me and rolled me over. Taking a bottle of lube from the nightstand, she proceeded to grease up my asshole for the anal invasion that was to come.
I've had women use butt plugs on me before, but never anything too large. From the sounds of it, Amelia was using something a lot larger than anything I've been accustomed to.
"Get up on all fours," said Helena. "Stephen, you're gonna love this!" Helena was working her fingers in and out of my ass, helping to prepare me for Amelia's tool. I've got to admit, I was really getting turned on by Helena's fingers. She massaged me until my sphincter loosened and then shoved three fingers deep inside my ass. The sensation was unlike anything I had ever felt. Just as I was getting to really like what she was doing, she withdrew her fingers. "Okay, baby, he's all yours."
Not being able to see anything made each sensation seem exaggerated, but it only intensified the pleasure. I could feel the tip of Amelia's strap-on easing against my asshole. She must have had one hell of a strap-on, because it was warm and very soft, very lifelike, yet still hard where it needed to be. I took a deep breath as she slid the head of it into my ass. God, this was driving me crazy.
Helena had positioned herself underneath me, so that she was able to kiss me and offer her tits to my open mouth. I sucked greedily on her long, hard nipples as Amelia slowly fed me her "dick". Did I mention that it must have been one hell of a strap-on? This thing had the feel of the real thing, warm, wet and throbbing.
As I sucked on Helena's exquisite boobs, Amelia had buried herself inside my hot and tight ass. She began thrusting this thing in and out of me, panting as she increased the tempo. I was stuffed beyond belief, and yet the sensations were strangely delicious. I was enjoying my first ass fucking with a dildo, believe it or not.
Helena began to stroke my cock as Amelia continued fucking me. I was sure that I wouldn't last long, as both of these women were exciting every nerve ending in my body.
Amelia was moaning now. "Stephen, you feel so good, so good and tight. I'm almost ready to cum, baby!"
Huh? Feel so good and tight? Wow, she must have a rabbit attached to that thing if she was getting off. I know that I was about to give Helena a handful of hot cum any second now. The combination of being ass fucked along with Helena's expert hands was pushing me over the edge. Any minute now...
Just then Amelia screamed. "Oh dear God, I'm gonna cum! Take my cum, Stephen!"
The next several seconds was confusing, but Amelia had pulled out of my ass and flipped me onto my back. Her strength was amazing, as she tossed me on my back as if I were a mannequin.
As I lay there, my orgasm on hold, Helena ripped the blindfold off my face. There, staring me in the face, was Amelia. She had straddled my chest and was thrusting a wet, throbbing cock into my face. Wait a minute, I thought. Then it hit me.
A COCK!! It was a real, live COCK!! As I became aware of what was going on, Amelia pointed it at my gaping mouth and began to shoot streams of cum at me. Some of it went into my open mouth, some went all over my face and still more of it landed in my hair and onto the bed. I was gagging and spurting as the hot, sticky fluid went down my throat and I involuntarily swallowed. Amelia began to rub her cock all over my face, smearing her cum all over me. Helena was licking it off my face and gulping down what she could.
Then Amelia rubbed her huge cock on my lips. I tried to resist what she was doing, which was forcing my mouth open so that I could suck her clean, but then Helena spoke to me in a peaceful, calming voice.
"Go ahead and take it, Stephen. It's what I want. Believe me, you'll love it as much as I do."
I was repulsed by the thought of sucking this tranny's cock, but I had to think about the big picture. Reluctantly, I opened my mouth and took her cock. It was covered in cum and still semi-hard. I licked the cum away and even began to suck on it. Strangely, after the first few seconds the revulsion went away, replaced by an odd desire to suck her cock clean. I found myself becoming hard again, and Helena squeezed my cock as if she were milking a cow. Gulping down Amelia's cum and my own ass juices seemed to turn me on and, with Helena's aid, I found myself ready to cum.
Amelia pulled her cock from my mouth and positioned herself alongside Helena. As my cock began spurting my seed, the two of them took turns sucking my dick and receiving the hot jets of my cum. They licked it, licked each other and gulped down my essence. When I finished spraying them with my cum, they fell back on the bed. Amelia pulled me down so that we could lie there together.
What a sight it must have been, the three of us lying together on the bed, our faces caked with the dry residue of mine and Amelia's cum. Helena broke the silence first.
"Stephen, I apologize for deceiving you, and for using the blindfold, but you surely would have balked if you knew about Amelia from the beginning. You'll have to admit, though, that it was unlike anything you've ever done. Be honest with me now, did you enjoy yourself?"
"Strangely enough, Helena, I did. I must have been something to see when Amelia stuck her cock in my face, but once I took her into my mouth it was as arousing as anything I have ever done. Amelia, you were wonderful tonight. You got two of my cherries in one evening."
Amelia laughed at that one. "You know, Stephen, you were a good sport about it. It's not often that Helena and I are able to find a willing partner, but you have been the best one so far. Would you be willing to try it again sometime?"
"I might , Amelia, I just might. You've opened the door to some interesting things tonight. I wouldn't mind getting inside that beautiful ass of yours someday, that's for sure."
"Then I'll have to set something up for another day," said Helena. "I'm much too tired after all of this tonight, but I promise we'll get together real soon. Amelia, what do you say we get our boy toy cleaned and dressed? I'm sure that he could use some sleep after giving two women such a wonderful time."
The two of them led me to the bathroom. Helena had a massive walk-in shower, with shower heads on three sides. They led me in and we washed each other until we were sparkling clean. I found myself getting aroused again when Amelia had me wash her huge cock. It was still a little strange, running my hands along the shaft of another cock, but it was very erotic, and opened my mind to many new possibilities for the future.
After we dried ourselves and got me dressed, the two ladies gave me goodnight kisses. They never did get dressed, and I assumed that they were going to spend the night here in Helena's bed.
Walking me to the elevator door, Helena had some parting words for me.
"Stephen, I can't thank you enough for a wild and wonderful evening. I'll be sure to tell Jessica that you went above and beyond my expectations tonight. I'll leave out some of the kinkier details, but I'm sure she will be pleased. The driver will take you back home as soon as you reach the ground floor. You have a good night, Stephen. Don't forget about our offer of doing this again. We'd love to see where we can take you with more time on our hands." She then took my head in her hands and gave me a sweet, tender kiss.
"Thank you for everything, Helena," I said. "I really enjoyed myself, once I let my inhibitions go. I'll keep your offer in mind. Get in touch with me when you want to do part two." I handed her one of my business cards. I was serious about getting together with them again.
Once I got back to my place I took stock of the evening. Once things got hot back in Helena's apartment I began to really enjoy myself, despite my original displeasure at being with a transsexual. All in all, things turned out pretty well.
Sleep came quickly, as the two women had really worn me out.
The next morning I arrived at the firm and began going over my schedule for the day as I had a large cup of coffee. As I went over my schedule, mail arrived from Molly. Jessica requested my presence at 11:30 again. I wondered if this was going to be her modus operandi, calling me in to tell me that she had a friend in need of servicing. Oh well, I thought, this is what I signed up for. That little bit of rationalization was what kept me from thinking of myself as Jessica's male whore. The problem was, I was already beginning to enjoy my role.
I walked into Jessica's suite and there sat Molly. She had on a yellow floral top and a flowing white pleated skirt. I smiled as I saw her outfit. She was looking more feminine this morning, a far cry from the austere, masculine look I had always seen her in.
"Good morning, Molly," I said to her. "You're looking quite attractive in that outfit."
Molly just looked at me, no expression at all on her face, as usual. "How was your assignment last night, Mr. Kramer? Did you get a chance to meet Amelia?" This time she showed me a slightly wicked smile, like she knew all about what I was into last night. "She's something else, isn't she?" Now she had a huge smile on her face and I detected a little blushing going on.
I just smiled and winked at her as I went by to enter Jessica's office. One of these days, I thought to myself. One of these days...
Wynona
- 12.12.2021
- 7
- 0
- Category:
- Office Sex
Switch partner with my best friends
- 2 years ago
- 19
- 0
Woman Partner Chapter Thirteen My Coming Out Party
- 3 years ago
- 30
- 0
