Changing Professions Part Five
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Changing Professions: Part Four free porn video
Part Four: Working Girl
Eve has joined Inhibitions Unlimited as an escort hoping to substantially increase her income. Her first client was the town's first black Mayor. She role played as a young Dutch girl and from all indications, he was well satisfied. In addition, she is looking forward to a starring role in a new porn flick called "The Principal." Everything is working out just fine since leaving her third grade teaching position or so it seems.
Tommy's survey was simple to complete. He had listed every sex act imaginable and all I needed to do was check off those that I had provided for the Mayor. There was a section for comments but there wasn't anything about the Mayor that was unusual except for having me suck his cum out of the condom. I just confirmed his preference for licking pussy and that it was best to remind him to use a condom. Oh, and I listed the time as one hour, forty minutes.
Several days later, Barbara had posted a copy of the Mayor's bill on my personal site. It indicated an hour and a half at $600 per hour "normal fee" for "services rendered" plus $150 for the hospitality room. The total was $1050 and billed to the city's Health and Human Services Department. I can't name the city here but it is pretty well known in the Midwest. I was credited with earning $577.50 and the city paid for their Mayor's evening of entertainment. It's good to be the Mayor!
Over the next several weeks, I screwed short guys, tall guys, fat and thin guys, ugly men and one young handsome boy. Most of the handsome men don't seem to need an escort service since they get their needs met from horny ambitious office girls.
Playing a school girl was very popular and it was easy for me having been a teacher. I entertained them at different condos, never the same place twice in a row. There was even a female customer, and to tell the truth, I was at a loss at how to deal with the situation. She was a late middle aged lady with the largest nipples I'd ever seen. She called herself Mona, and me Darlin'. Mona had a relaxed manner and made both of us feel at ease. Women have an intuition about these things. She also wasn't shy about telling me what she wanted. I began by licking her tits and as I took her huge nipple in my mouth, I thought of a calf suckling its mother. Although I had lady toys with which to amuse her, she wanted to use a wine bottle. The interesting part was that the bottle wasn't empty when I stuck it in her cunt. Using her the sweet ladylike manner, she had me drink the wine as it leaked from her pussy.
Every situation was uneventful and I felt more secure with each encounter. Most of the men were married and very few of their wives let them do anal. So, my butt hole got a workout so I ask the maid to bring an extra supply of lubricants. Some were used to make the dildos more slippery but most were needed to make anal more comfortable. I was a little tender back there during the first week but the thing is, I was making tons of money just like Jan had said.
Toward the end of my first month as a call girl, I did two guys on the same day, one in the afternoon and the second around ten in the evening. That was the first time Barb scheduled me with two appointments close together. As business picked up, I found myself doing two-a-days more often and even three. The good news was that during my first month, I earned $7000. Remember, Tommy and Barbara pay in cash so it was tax free. I was clearly on a path to owning my own BMW.
One Sunday afternoon, Barbara called asking me to fill in for one of the other girls to service a client that evening. Apparently, the original booking was with Sarah who was having a bad time with cramps. Having a girl's period is always disruptive but in this business, it really sucks. I was relatively new on the team and didn't want to disappoint the boss so I agreed to do it. The man was in his seventies and arrived with a little black bag, like a doctor's bag, that made me nervous. His name was Sam. Would this be some kind of kinky bondage or SM role playing? There was nothing on Sam's profile to suggest my role was to be his slave.
It turned out that the old man brought along a few sexual aids including a penis pump, a cock ring and other implements to help him perform. Sam knew getting it up would be a problem. Even with Viagra, an erection was a major challenge for him. He was delightfully polite and gracious. I liked him like a grandfather. I tickled his balls and pumped him until he got close to getting hard enough to have intercourse. Over a period of time, his penis was firm, not hard and he was able to get inside me. Sam wasn't a great fuck but I felt sorry for him and told him he was a great lover. He thanked me but he knew I was lying.
Before leaving he said, "The thing is, I did this to feel young again, just one last time. Thank you."
I smiled and gave him a big hug saying, "You'll always be young at heart."
Again he thanked me and said, "You are a very sweet girl." At that, he turned and shuffled out the door. Sad, so sad.
There was another customer I have to tell you about. It was Charlie and he had just turned 18. His dad had booked our escort service for his son's birthday present because, as it turned out, Charlie was a virgin. Charlie was tall, maybe six feet, five inches with a chiseled face and a muscular body. The boy was gorgeous! I could see right away he was scared stiff, but not stiff in the right place.
I started by asking him about school and his girlfriend. I wondered, "Could he have been a former student where I taught third grade?" I didn't ask. We talked about sports. He was a basketball player. He said he had a scholarship at Duke.
Then I asked him about sex. He looked away and said, "I don't know much about it except what I see on the internet."
Trying to get his juices flowing, I asked, "Charlie, have you seen your girlfriend naked? No, he said, but he had jacked off to lots of nude pictures of girls on his computer." I told him that was fine and a good release. I wanted to reassure him that sex, even masturbation, is normal.
Then I asked, "How about if I show you what it is like to be with a live nude girl. Would you like that?"
"Yes, but should I take off my clothes?"
"If you like," I replied and provocatively removed my blouse. He followed by taking off his shirt. Then I slid my skirt down around my ankles turning to show my ass. Wearing a only a tiny thong, he had an unobstructed view of my nicely formed ass cheeks.
While he was removing his pants, I slowly unhooked my bra. I wanted Charlie to see my breasts fall out of the bra in a way that he couldn't help but get aroused. That little subtlety always gets men harder than a lead pipe. There I was seducing Charlie, wearing only a red thong barely covering my pussy lips and fuck me heals. Charlie was down to his shorts.
Things were not working out as planned. There was no bulge in the boy's shorts indicating he wasn't ready for us to fuck. Time for Plan B. I sat across from Charlie, teasing him saying, "Did you see a picture like this?" as I lifted a breast up to my waiting tongue.
Charlie was embarrassed and said, "Yes, I guess."
"Charlie, have you seen a girl spread her pussy?" I demonstrated.
"Yeah," and his face flushed.
"How about this?" and I plunged two fingers in my slit.
"Maybe," he said. But after all of my efforts to seduce Charlie, he was still showing no sign of an erection.
Finally I said, "Okay, Charlie, here's where I show you what a woman can do for a real man like you. I gradually pulled off his shorts and held his limp cock in my hand waiting for it to respond. It didn't. I began licking his balls smearing saliva around his plump sack, still waiting for his organ to stiffen. It didn't work. The boy was just too frightened to relax.
"Charlie, I'm going to suck on your cock and you pretend you are in your bedroom, all alone, massaging yourself. Okay?"
"Okay," he nervously replied.
I put him in my mouth and swirled my tongue around his soft dick pressing my lips against his manhood. It was hard work but I loved the challenge. Well, I love cock to be honest. Anyway, it took another few minutes until Charlie began to relax. I sat him on the couch and opened his legs continuing to work on him.
Finally I could feel his manly hose begin to stir. As his cock grew, I was overjoyed to see that Charlie was well endowed. At full erection, he had the most beautiful specimen I had ever seen since working as a whore. All I could think of was getting his youthful shaft into my pussy. This was going to be fun.
I held onto his now rigid cock and led him to the promise land, the bedroom. I was so ready, wet and anxious to have him sliding inside me. I imagined holding my knight's lance that now stood past his thighs by at least eight inches. He was unsure what to do next but what is a teacher to do but teach? I had taken some really large cocks in my mouth in the past but Charlie's was a challenge.
"Charlie, do you know what it means to deep throat?"
He sat on the edge of the bed and nodded that he understood. I wet my lips and began to impale my throat with his lance. I got down all but an inch of him thinking it was impossible to get him in further. With one last dedicated plunge, I forced that magnificent spear to the limit. He moaned as saliva trickled past my lips onto his balls. The taste of his pre-cum was yummy especially with an anticipation there would be more to cum.
We laid on the bed together for a few minutes while I stroked his shaft. This short foreplay ended when I spread my legs and gently pulled him over onto me. I could feel his erection on my belly and reached down to put it between my thighs.
"Come on Charlie, get yourself inside me. I'll help." I grabbed his marvelous tool and placed it in front of my pussy lips. At first, I rubbed his cock head between the folds of my pussy and on my clit, letting out a quiet whimper. "Now just stick it in and let me feel your hot cock inside me."
He did what I said. At first, my young knight seemed cautious but with a little encouragement, his cock slid into my slippery love hole with no resistance. I said, "Now fuck me, Charlie."
Apparently, he knew what that meant and pressed inward, pumping with progressively longer strokes, sliding in and out, slowly at first then picking up the pace. I was fully aroused feeling the orgasm that had steadily been building. His young virgin cock filling my vagina was a sinfully decadent feeling, a gift from the gods.
I cried out, "More, Charlie. Deeper, Charlie. Harder, Charlie." He needed no further instruction. He slammed his thick pulsating dick all the way in, up to the hilt and I could feel him ejaculating a steady stream of sticky cum into me. At the same moment, I squealed, "I'm cumming, Charlie, I'm cumming."
A wave of orgasmic pleasure washed over my entire body with tears streaming down my cheeks. His cum continued to gush inside my fuck canal until he finished with a final energetic thrust.
We just lay there for a few minutes, connected, with neither of us wanting to break the spell. Later when he finally pulled out, our mutual orgasm was evident by a gooey slick mess coating his massive dick and more dripping out of my cunny slit. I was totally in dreamsville.
"Ma'am, did I hurt you?" he asked noticing my tears.
"No Charlie, those are tears of joy."
His father had paid for two hours so we had another hour left. I didn't want it to end and hoped Charlie could recover for another round.
I said, "Charlie, the next time you fuck a girl, you need to wear a condom."
"Fine, but my dad didn't give me any."
"Before you leave, I'll give you some "to go," I said like a barista at the coffee shop. "Are you ready to do it again but maybe in a different way?" I asked.
"Sure, but give me a minute because I'm feeling tired."
We talked awhile and then I asked him if he was ready. He said he wasn't so this gave me a chance to teach him how to pleasure a woman.
"Charlie, come over here and play with my pussy." I took his hand and pressed it against my moist cunt.
"Mam, that feels so soft and wet."
"That's right, Charlie. When a woman is excited she has those natural juices and I'd like you to taste my juices. Bring your head down between my legs and lick me." My young stud did as he was instructed. I asked him how it tasted.
He said, "I'm not sure, kind of salty."
"You're probably tasting the semen you shared with me awhile ago. You haven't tasted your cum before?"
"No, I guess not."
"It's sexy when a guy licks his his own cum off a girl. Lick me clean, Charlie."
And he did what I asked.
I was in the teaching mode again when I said, "Charlie, do you see that little button just above my girly hole? That is what really gives a girl pleasure. Please lick it and suck on it. If you do it well, it should get swollen and it will give me lots of pleasure."
It didn't take long for him to learn to give great head. He was a natural. And it didn't take long for me to be on the verge of my second orgasm.
Finally, the pole proudly standing out between his legs told me that he was ready to fuck again. I reasoned that since Charlie had fucked me without protection the first time, there was no need cover him now. After all, he was a virgin and I love the feeling of cum shooting into my cervix. I turned over on all fours and showed him how to enter me doggie style. He humped me good for what seemed like hours bringing us both to a second orgasm.
It turned out that Charlie was quite the guy. He had real staying power. After ejaculating twice and with a little more rest, he came again in the third act. I showed him cowgirl. He grabbed my tits and held them firmly as I rode him up and down bronco style. When he was ready, I had him squirt my mouth with what was still an amazing amount of jizz. I, of course, was thrilled to be a teacher again and both the teacher and student were totally satisfied with the lesson.
Before he left he said, "Thanks, that was great. Can I buy one of your videos?"
"Sure, take it. It's free."
"Oh my dad said you probably would expect a tip. How much should I give you?"
"Forget it, Charlie. You made me very happy in bed tonight. You will make some woman a very good lover. By the way, I'm curious. When was the last time you jacked off?"
Embarrassed he said, "Last week, my dad said to save it for tonight."
"You did well, Charlie. Not many men can cum like you did."
He took the video and I sent him on his way with a six pack of condoms. The maid was on her way to the apartment as I was leaving and I hoped she had brought along an air freshener. The place reeked of sex. I stopped at the pharmacy to pick up the morning after pill since my birth control prescription ran out last month and I never got around to getting a refill. I was soon home fantasizing about another night with my young knight.
I never saw Charlie again but his dad left a nice tip on the credit card.
The following month I earned over $10,000 and Tommy gave me the apartment. In addition, my hourly rate increased to $750 due to my growing popularity. Barbara also required clients to pay for a two-hour minimum per engagement. For the agency, I had become a cash cow.
Barbara and Tommy bought a fifth condo shortly after my second month and it occurred to me that their business plan was to build a real estate empire on the backs of us girls. Eventually, it seemed, they would sell the escort service and rent out the apartments. Brilliant!
My bank balance was also prospering growing like kudzu on a telephone pole. I even opened an account at Fidelity to invest in a few mutual funds. Things were going really well for all of us but as we all know, for every action there is an equal and opposite reaction. There are consequences.
Dressing in different costumes made me feel sexy and like a real actress. When not in costume, I would greet the customer braless with my tits bursting out of an undersized tank top. Guys liked the look and enjoyed unwrapping my package. Sometimes, anticipating the delights of a woman is as good as actually experiencing it. Men liked what they saw by the time they removed the last ribbon, usually a thong or g-string.
One guy wanted me in panties so he could take a scissors to cut an opening in front of my pussy. Then he'd fuck me through that hole without removing the panties. Different strokes for different folks. There are so many fantasies to be satisfied and that's why this job was never boring.
I enjoyed posing nude and to increase the sexual heat, I'd shake and play with my tits. It was always met with overwhelming approval. In the bedroom, the basics are net stockings, teddies, garters and garter belts. Among the most effective was sexy lingerie that would even make Victoria's Secret blush. They always did the job for which they were intended.
Baby doll lingerie was particularly popular and there was one that drove most guys absolutely wild. It was a see-through baby doll that accentuated my already ample breasts. When my nipples got hard, a man was treated to seeing them poke through tiny holes in the fabric. The g-string left nothing to a man's imagination. There was never a guy that didn't get an instant hard-on seeing me in it. This, of course, made my job a lot easier. These costumes were what primed the pump!
Our Mayor made several more visits. He loved the tantalizing French maid outfit. Once I dressed as a fraulein in native Bavarian dress. Actually, I got some good ideas from a video, Fraulein in Uniforme. Well, sometimes the frauleins were in uniform but not often.
Another time, I told the Mayor how Nazi soldiers had tortured and raped me and I needed a strong American man to protect me. He fell for it hook line and sinker.
The Mayor booked me during the Christmas holidays. I was a girl dressed in Swedish holiday clothes. My blond hair worked well in this role play. I was Lucia, the Swedish girl that was martyred and killed for her faith. However, I altered the story somewhat. Instead of bringing food to the persecuted Christians, Lucia provided sexual favors. The Mayor was not familiar with the St. Lucia story but believe me, by the end of our session, he had a pretty good idea what it was about.
He was delighted with the Swedish girl and gave me the biggest tip so far in my fledgling career. The most interesting part was that each encounter with the Mayor was billed to a different city department. This was a clever way to cover his tracks.
"Jaws" rang on my phone one afternoon when business was slow. It was the time of year when the rich and famous were away on vacation: in Switzerland, The Hamptons, or Hawaii. However, the following month was the beginning of convention season. That's when I easily made up for lost revenue when conventioneers hit town.
The ringtone played on and I finally answered. "Hello?"
"Hi, this is a friend that saved you from the Nazis," the voice whispered on the other end.
"Oh, hi." I recognized the Mayor's voice. "Shouldn't you be contacting me through the website?"
"No, I'm not scheduling another appointment but would like to speak with you about a business proposition."
"Really?" I was truly surprised.
"Yes. Can you meet me for dinner at the Como?"
"What's this about?"
"I'll tell you at dinner. You won't be disappointed"
I thought a minute and wondered if this was within company policy. Well, Barbara said it was okay to have dinner with clients but she didn't say if it would be fine without entertaining them for a price.
"I think it's alright. What time?"
"I'll have a limo pick you up in front of the same place we met last week. Make it 6:30."
"Okay, I'll be there." This was an ideal arrangement because that condo was where I lived.
I was escorted to a private room in the Como. I knew there was a VIP room but never worked the room when employed as a waitress at the Como. The Mayor had already arrived and stood to greet me.
"Welcome Eve. Please sit down."
"How did he know my real name?" I wondered. The maitre d' helped me be seated. This was the same man that fired me for not giving him blow jobs and must have been curious why I was there with the Mayor. Neither of us let on that we knew each other.
"Eve, I'm sure you know who I am. Being rather well known, I appreciate your discretion regarding our association. I know I can trust you."
"Thank you, Mayor Johnson," I replied in a soft tone.
"Let's enjoy some Champagne and we'll talk business over dinner. I've ordered baked flounder for the entrée. It's freshly caught and the chef has a fantastic recipe. The Como has the best seafood in the city. I hope you will like it."
"I'm sure I will, Mayor." That part was genuine because when I worked at the Como, it was among the most popular dishes. It's just that I could never afford it.
We sipped our chilled Champagne and munched on a delightful shrimp cocktail. Most of our conversation centered around the Mayor's work and his upcoming reelection campaign. I was still curious why we were dining together without a reservation through And how did he know my name? Somebody squealed but then mayors have their ways and lots of clout. Midway through the succulent flounder, Mayor Johnson began telling me how difficult it was finding a private secretary with just the right qualifications. Finally getting to the point, he said, "I'd like you to fill that position for me."
The Mayor was offering me a job. Wow! I never would have guessed as much. So that was one of the consequences of success it seemed.
He went on, "The office part is rather easy. You would answer my private calls and do some filing. It really doesn't amount to much. Mostly you would dress well wearing fine but understated jewelry while welcoming visitors. If you need help with that, I have a rather generous expense account. There would be some travel because you will always be at my side during trips. I need someone to make me look good and keep me company." He smiled.
"Perhaps the most important part of the job is to host an occasional private party for dignitaries and colleagues. That's very important in politics. The pay is good. The starting salary is $125,000."
I said nothing and listened when he mentioned that I would have to leave my current employment and work only for him. The city would lease an apartment for me and all entertaining would take place there. The expense is within the Political Functions/Entertainment budget. "Holy buggers," I thought. He wants his own private fuck girl, a mistress.
We ordered dessert but I only picked at it.
When we got up to leave I said, "Mayor, I really appreciate your offer but I need time to think it over."
"That's fine, Eve. I figured you would need some time on this. Call me when you make a decision. Here is my card with my private number. I need to know by Thursday. The limo driver will take you back to your condo."
That gave me two days to decide. I was back home at nine that evening doing my homework. It wasn't a simple decision but one thing kept creeping into the back of my mind, "What if he isn't reelected?" The other consideration was the money. I already lived in a very nice apartment and I was now averaging $12,000 a month. That's something like a hundred forty grand a year, tax free! So, I thought I'd run this by Jan. I called her that night and heard, "Hi, this is Jan. I'm out. Leave your name and number and I'll return your call." I left my name.
She called back the next morning and apologized for the delay. Jan had been performing a much needed service to one of our top military generals and it ran later than usual. "So Eve, what's up?"
I explained the deal. She was a great help by reinforcing my thoughts about the election and money. In the end, we both decided it was best to turn down the offer. The one concern we both had was the Mayor might turn vindictive and close down the agency.
I called Tommy to explain what had happened and told him I had not taken the Mayor's offer. He said not to worry about the Mayor. Mayor Johnson is a good man. If he decides to apply some heat, we have his record on file.
"Oh, and Eve, something's came up and I need to speak with you right away. This is an out of agency situation and maybe we can talk about it at your apartment."
"Why not tell me now?" I inquired.
"Well, it's a delicate matter. I'll be there in an hour," he said and hung up.
Oh boy, another mystery for me to ponder. For Tommy to come to my place and on such short notice, it must be important. He said it wasn't about the agency so what could be so pressing?
See what's in store for Eve in Part Five
Eve has joined Inhibitions Unlimited as an escort hoping to substantially increase her income. Her first client was the town's first black Mayor. She role played as a young Dutch girl and from all indications, he was well satisfied. In addition, she is looking forward to a starring role in a new porn flick called "The Principal." Everything is working out just fine since leaving her third grade teaching position or so it seems.
Tommy's survey was simple to complete. He had listed every sex act imaginable and all I needed to do was check off those that I had provided for the Mayor. There was a section for comments but there wasn't anything about the Mayor that was unusual except for having me suck his cum out of the condom. I just confirmed his preference for licking pussy and that it was best to remind him to use a condom. Oh, and I listed the time as one hour, forty minutes.
Several days later, Barbara had posted a copy of the Mayor's bill on my personal site. It indicated an hour and a half at $600 per hour "normal fee" for "services rendered" plus $150 for the hospitality room. The total was $1050 and billed to the city's Health and Human Services Department. I can't name the city here but it is pretty well known in the Midwest. I was credited with earning $577.50 and the city paid for their Mayor's evening of entertainment. It's good to be the Mayor!
Over the next several weeks, I screwed short guys, tall guys, fat and thin guys, ugly men and one young handsome boy. Most of the handsome men don't seem to need an escort service since they get their needs met from horny ambitious office girls.
Playing a school girl was very popular and it was easy for me having been a teacher. I entertained them at different condos, never the same place twice in a row. There was even a female customer, and to tell the truth, I was at a loss at how to deal with the situation. She was a late middle aged lady with the largest nipples I'd ever seen. She called herself Mona, and me Darlin'. Mona had a relaxed manner and made both of us feel at ease. Women have an intuition about these things. She also wasn't shy about telling me what she wanted. I began by licking her tits and as I took her huge nipple in my mouth, I thought of a calf suckling its mother. Although I had lady toys with which to amuse her, she wanted to use a wine bottle. The interesting part was that the bottle wasn't empty when I stuck it in her cunt. Using her the sweet ladylike manner, she had me drink the wine as it leaked from her pussy.
Every situation was uneventful and I felt more secure with each encounter. Most of the men were married and very few of their wives let them do anal. So, my butt hole got a workout so I ask the maid to bring an extra supply of lubricants. Some were used to make the dildos more slippery but most were needed to make anal more comfortable. I was a little tender back there during the first week but the thing is, I was making tons of money just like Jan had said.
Toward the end of my first month as a call girl, I did two guys on the same day, one in the afternoon and the second around ten in the evening. That was the first time Barb scheduled me with two appointments close together. As business picked up, I found myself doing two-a-days more often and even three. The good news was that during my first month, I earned $7000. Remember, Tommy and Barbara pay in cash so it was tax free. I was clearly on a path to owning my own BMW.
One Sunday afternoon, Barbara called asking me to fill in for one of the other girls to service a client that evening. Apparently, the original booking was with Sarah who was having a bad time with cramps. Having a girl's period is always disruptive but in this business, it really sucks. I was relatively new on the team and didn't want to disappoint the boss so I agreed to do it. The man was in his seventies and arrived with a little black bag, like a doctor's bag, that made me nervous. His name was Sam. Would this be some kind of kinky bondage or SM role playing? There was nothing on Sam's profile to suggest my role was to be his slave.
It turned out that the old man brought along a few sexual aids including a penis pump, a cock ring and other implements to help him perform. Sam knew getting it up would be a problem. Even with Viagra, an erection was a major challenge for him. He was delightfully polite and gracious. I liked him like a grandfather. I tickled his balls and pumped him until he got close to getting hard enough to have intercourse. Over a period of time, his penis was firm, not hard and he was able to get inside me. Sam wasn't a great fuck but I felt sorry for him and told him he was a great lover. He thanked me but he knew I was lying.
Before leaving he said, "The thing is, I did this to feel young again, just one last time. Thank you."
I smiled and gave him a big hug saying, "You'll always be young at heart."
Again he thanked me and said, "You are a very sweet girl." At that, he turned and shuffled out the door. Sad, so sad.
There was another customer I have to tell you about. It was Charlie and he had just turned 18. His dad had booked our escort service for his son's birthday present because, as it turned out, Charlie was a virgin. Charlie was tall, maybe six feet, five inches with a chiseled face and a muscular body. The boy was gorgeous! I could see right away he was scared stiff, but not stiff in the right place.
I started by asking him about school and his girlfriend. I wondered, "Could he have been a former student where I taught third grade?" I didn't ask. We talked about sports. He was a basketball player. He said he had a scholarship at Duke.
Then I asked him about sex. He looked away and said, "I don't know much about it except what I see on the internet."
Trying to get his juices flowing, I asked, "Charlie, have you seen your girlfriend naked? No, he said, but he had jacked off to lots of nude pictures of girls on his computer." I told him that was fine and a good release. I wanted to reassure him that sex, even masturbation, is normal.
Then I asked, "How about if I show you what it is like to be with a live nude girl. Would you like that?"
"Yes, but should I take off my clothes?"
"If you like," I replied and provocatively removed my blouse. He followed by taking off his shirt. Then I slid my skirt down around my ankles turning to show my ass. Wearing a only a tiny thong, he had an unobstructed view of my nicely formed ass cheeks.
While he was removing his pants, I slowly unhooked my bra. I wanted Charlie to see my breasts fall out of the bra in a way that he couldn't help but get aroused. That little subtlety always gets men harder than a lead pipe. There I was seducing Charlie, wearing only a red thong barely covering my pussy lips and fuck me heals. Charlie was down to his shorts.
Things were not working out as planned. There was no bulge in the boy's shorts indicating he wasn't ready for us to fuck. Time for Plan B. I sat across from Charlie, teasing him saying, "Did you see a picture like this?" as I lifted a breast up to my waiting tongue.
Charlie was embarrassed and said, "Yes, I guess."
"Charlie, have you seen a girl spread her pussy?" I demonstrated.
"Yeah," and his face flushed.
"How about this?" and I plunged two fingers in my slit.
"Maybe," he said. But after all of my efforts to seduce Charlie, he was still showing no sign of an erection.
Finally I said, "Okay, Charlie, here's where I show you what a woman can do for a real man like you. I gradually pulled off his shorts and held his limp cock in my hand waiting for it to respond. It didn't. I began licking his balls smearing saliva around his plump sack, still waiting for his organ to stiffen. It didn't work. The boy was just too frightened to relax.
"Charlie, I'm going to suck on your cock and you pretend you are in your bedroom, all alone, massaging yourself. Okay?"
"Okay," he nervously replied.
I put him in my mouth and swirled my tongue around his soft dick pressing my lips against his manhood. It was hard work but I loved the challenge. Well, I love cock to be honest. Anyway, it took another few minutes until Charlie began to relax. I sat him on the couch and opened his legs continuing to work on him.
Finally I could feel his manly hose begin to stir. As his cock grew, I was overjoyed to see that Charlie was well endowed. At full erection, he had the most beautiful specimen I had ever seen since working as a whore. All I could think of was getting his youthful shaft into my pussy. This was going to be fun.
I held onto his now rigid cock and led him to the promise land, the bedroom. I was so ready, wet and anxious to have him sliding inside me. I imagined holding my knight's lance that now stood past his thighs by at least eight inches. He was unsure what to do next but what is a teacher to do but teach? I had taken some really large cocks in my mouth in the past but Charlie's was a challenge.
"Charlie, do you know what it means to deep throat?"
He sat on the edge of the bed and nodded that he understood. I wet my lips and began to impale my throat with his lance. I got down all but an inch of him thinking it was impossible to get him in further. With one last dedicated plunge, I forced that magnificent spear to the limit. He moaned as saliva trickled past my lips onto his balls. The taste of his pre-cum was yummy especially with an anticipation there would be more to cum.
We laid on the bed together for a few minutes while I stroked his shaft. This short foreplay ended when I spread my legs and gently pulled him over onto me. I could feel his erection on my belly and reached down to put it between my thighs.
"Come on Charlie, get yourself inside me. I'll help." I grabbed his marvelous tool and placed it in front of my pussy lips. At first, I rubbed his cock head between the folds of my pussy and on my clit, letting out a quiet whimper. "Now just stick it in and let me feel your hot cock inside me."
He did what I said. At first, my young knight seemed cautious but with a little encouragement, his cock slid into my slippery love hole with no resistance. I said, "Now fuck me, Charlie."
Apparently, he knew what that meant and pressed inward, pumping with progressively longer strokes, sliding in and out, slowly at first then picking up the pace. I was fully aroused feeling the orgasm that had steadily been building. His young virgin cock filling my vagina was a sinfully decadent feeling, a gift from the gods.
I cried out, "More, Charlie. Deeper, Charlie. Harder, Charlie." He needed no further instruction. He slammed his thick pulsating dick all the way in, up to the hilt and I could feel him ejaculating a steady stream of sticky cum into me. At the same moment, I squealed, "I'm cumming, Charlie, I'm cumming."
A wave of orgasmic pleasure washed over my entire body with tears streaming down my cheeks. His cum continued to gush inside my fuck canal until he finished with a final energetic thrust.
We just lay there for a few minutes, connected, with neither of us wanting to break the spell. Later when he finally pulled out, our mutual orgasm was evident by a gooey slick mess coating his massive dick and more dripping out of my cunny slit. I was totally in dreamsville.
"Ma'am, did I hurt you?" he asked noticing my tears.
"No Charlie, those are tears of joy."
His father had paid for two hours so we had another hour left. I didn't want it to end and hoped Charlie could recover for another round.
I said, "Charlie, the next time you fuck a girl, you need to wear a condom."
"Fine, but my dad didn't give me any."
"Before you leave, I'll give you some "to go," I said like a barista at the coffee shop. "Are you ready to do it again but maybe in a different way?" I asked.
"Sure, but give me a minute because I'm feeling tired."
We talked awhile and then I asked him if he was ready. He said he wasn't so this gave me a chance to teach him how to pleasure a woman.
"Charlie, come over here and play with my pussy." I took his hand and pressed it against my moist cunt.
"Mam, that feels so soft and wet."
"That's right, Charlie. When a woman is excited she has those natural juices and I'd like you to taste my juices. Bring your head down between my legs and lick me." My young stud did as he was instructed. I asked him how it tasted.
He said, "I'm not sure, kind of salty."
"You're probably tasting the semen you shared with me awhile ago. You haven't tasted your cum before?"
"No, I guess not."
"It's sexy when a guy licks his his own cum off a girl. Lick me clean, Charlie."
And he did what I asked.
I was in the teaching mode again when I said, "Charlie, do you see that little button just above my girly hole? That is what really gives a girl pleasure. Please lick it and suck on it. If you do it well, it should get swollen and it will give me lots of pleasure."
It didn't take long for him to learn to give great head. He was a natural. And it didn't take long for me to be on the verge of my second orgasm.
Finally, the pole proudly standing out between his legs told me that he was ready to fuck again. I reasoned that since Charlie had fucked me without protection the first time, there was no need cover him now. After all, he was a virgin and I love the feeling of cum shooting into my cervix. I turned over on all fours and showed him how to enter me doggie style. He humped me good for what seemed like hours bringing us both to a second orgasm.
It turned out that Charlie was quite the guy. He had real staying power. After ejaculating twice and with a little more rest, he came again in the third act. I showed him cowgirl. He grabbed my tits and held them firmly as I rode him up and down bronco style. When he was ready, I had him squirt my mouth with what was still an amazing amount of jizz. I, of course, was thrilled to be a teacher again and both the teacher and student were totally satisfied with the lesson.
Before he left he said, "Thanks, that was great. Can I buy one of your videos?"
"Sure, take it. It's free."
"Oh my dad said you probably would expect a tip. How much should I give you?"
"Forget it, Charlie. You made me very happy in bed tonight. You will make some woman a very good lover. By the way, I'm curious. When was the last time you jacked off?"
Embarrassed he said, "Last week, my dad said to save it for tonight."
"You did well, Charlie. Not many men can cum like you did."
He took the video and I sent him on his way with a six pack of condoms. The maid was on her way to the apartment as I was leaving and I hoped she had brought along an air freshener. The place reeked of sex. I stopped at the pharmacy to pick up the morning after pill since my birth control prescription ran out last month and I never got around to getting a refill. I was soon home fantasizing about another night with my young knight.
I never saw Charlie again but his dad left a nice tip on the credit card.
The following month I earned over $10,000 and Tommy gave me the apartment. In addition, my hourly rate increased to $750 due to my growing popularity. Barbara also required clients to pay for a two-hour minimum per engagement. For the agency, I had become a cash cow.
Barbara and Tommy bought a fifth condo shortly after my second month and it occurred to me that their business plan was to build a real estate empire on the backs of us girls. Eventually, it seemed, they would sell the escort service and rent out the apartments. Brilliant!
My bank balance was also prospering growing like kudzu on a telephone pole. I even opened an account at Fidelity to invest in a few mutual funds. Things were going really well for all of us but as we all know, for every action there is an equal and opposite reaction. There are consequences.
Dressing in different costumes made me feel sexy and like a real actress. When not in costume, I would greet the customer braless with my tits bursting out of an undersized tank top. Guys liked the look and enjoyed unwrapping my package. Sometimes, anticipating the delights of a woman is as good as actually experiencing it. Men liked what they saw by the time they removed the last ribbon, usually a thong or g-string.
One guy wanted me in panties so he could take a scissors to cut an opening in front of my pussy. Then he'd fuck me through that hole without removing the panties. Different strokes for different folks. There are so many fantasies to be satisfied and that's why this job was never boring.
I enjoyed posing nude and to increase the sexual heat, I'd shake and play with my tits. It was always met with overwhelming approval. In the bedroom, the basics are net stockings, teddies, garters and garter belts. Among the most effective was sexy lingerie that would even make Victoria's Secret blush. They always did the job for which they were intended.
Baby doll lingerie was particularly popular and there was one that drove most guys absolutely wild. It was a see-through baby doll that accentuated my already ample breasts. When my nipples got hard, a man was treated to seeing them poke through tiny holes in the fabric. The g-string left nothing to a man's imagination. There was never a guy that didn't get an instant hard-on seeing me in it. This, of course, made my job a lot easier. These costumes were what primed the pump!
Our Mayor made several more visits. He loved the tantalizing French maid outfit. Once I dressed as a fraulein in native Bavarian dress. Actually, I got some good ideas from a video, Fraulein in Uniforme. Well, sometimes the frauleins were in uniform but not often.
Another time, I told the Mayor how Nazi soldiers had tortured and raped me and I needed a strong American man to protect me. He fell for it hook line and sinker.
The Mayor booked me during the Christmas holidays. I was a girl dressed in Swedish holiday clothes. My blond hair worked well in this role play. I was Lucia, the Swedish girl that was martyred and killed for her faith. However, I altered the story somewhat. Instead of bringing food to the persecuted Christians, Lucia provided sexual favors. The Mayor was not familiar with the St. Lucia story but believe me, by the end of our session, he had a pretty good idea what it was about.
He was delighted with the Swedish girl and gave me the biggest tip so far in my fledgling career. The most interesting part was that each encounter with the Mayor was billed to a different city department. This was a clever way to cover his tracks.
"Jaws" rang on my phone one afternoon when business was slow. It was the time of year when the rich and famous were away on vacation: in Switzerland, The Hamptons, or Hawaii. However, the following month was the beginning of convention season. That's when I easily made up for lost revenue when conventioneers hit town.
The ringtone played on and I finally answered. "Hello?"
"Hi, this is a friend that saved you from the Nazis," the voice whispered on the other end.
"Oh, hi." I recognized the Mayor's voice. "Shouldn't you be contacting me through the website?"
"No, I'm not scheduling another appointment but would like to speak with you about a business proposition."
"Really?" I was truly surprised.
"Yes. Can you meet me for dinner at the Como?"
"What's this about?"
"I'll tell you at dinner. You won't be disappointed"
I thought a minute and wondered if this was within company policy. Well, Barbara said it was okay to have dinner with clients but she didn't say if it would be fine without entertaining them for a price.
"I think it's alright. What time?"
"I'll have a limo pick you up in front of the same place we met last week. Make it 6:30."
"Okay, I'll be there." This was an ideal arrangement because that condo was where I lived.
I was escorted to a private room in the Como. I knew there was a VIP room but never worked the room when employed as a waitress at the Como. The Mayor had already arrived and stood to greet me.
"Welcome Eve. Please sit down."
"How did he know my real name?" I wondered. The maitre d' helped me be seated. This was the same man that fired me for not giving him blow jobs and must have been curious why I was there with the Mayor. Neither of us let on that we knew each other.
"Eve, I'm sure you know who I am. Being rather well known, I appreciate your discretion regarding our association. I know I can trust you."
"Thank you, Mayor Johnson," I replied in a soft tone.
"Let's enjoy some Champagne and we'll talk business over dinner. I've ordered baked flounder for the entrée. It's freshly caught and the chef has a fantastic recipe. The Como has the best seafood in the city. I hope you will like it."
"I'm sure I will, Mayor." That part was genuine because when I worked at the Como, it was among the most popular dishes. It's just that I could never afford it.
We sipped our chilled Champagne and munched on a delightful shrimp cocktail. Most of our conversation centered around the Mayor's work and his upcoming reelection campaign. I was still curious why we were dining together without a reservation through And how did he know my name? Somebody squealed but then mayors have their ways and lots of clout. Midway through the succulent flounder, Mayor Johnson began telling me how difficult it was finding a private secretary with just the right qualifications. Finally getting to the point, he said, "I'd like you to fill that position for me."
The Mayor was offering me a job. Wow! I never would have guessed as much. So that was one of the consequences of success it seemed.
He went on, "The office part is rather easy. You would answer my private calls and do some filing. It really doesn't amount to much. Mostly you would dress well wearing fine but understated jewelry while welcoming visitors. If you need help with that, I have a rather generous expense account. There would be some travel because you will always be at my side during trips. I need someone to make me look good and keep me company." He smiled.
"Perhaps the most important part of the job is to host an occasional private party for dignitaries and colleagues. That's very important in politics. The pay is good. The starting salary is $125,000."
I said nothing and listened when he mentioned that I would have to leave my current employment and work only for him. The city would lease an apartment for me and all entertaining would take place there. The expense is within the Political Functions/Entertainment budget. "Holy buggers," I thought. He wants his own private fuck girl, a mistress.
We ordered dessert but I only picked at it.
When we got up to leave I said, "Mayor, I really appreciate your offer but I need time to think it over."
"That's fine, Eve. I figured you would need some time on this. Call me when you make a decision. Here is my card with my private number. I need to know by Thursday. The limo driver will take you back to your condo."
That gave me two days to decide. I was back home at nine that evening doing my homework. It wasn't a simple decision but one thing kept creeping into the back of my mind, "What if he isn't reelected?" The other consideration was the money. I already lived in a very nice apartment and I was now averaging $12,000 a month. That's something like a hundred forty grand a year, tax free! So, I thought I'd run this by Jan. I called her that night and heard, "Hi, this is Jan. I'm out. Leave your name and number and I'll return your call." I left my name.
She called back the next morning and apologized for the delay. Jan had been performing a much needed service to one of our top military generals and it ran later than usual. "So Eve, what's up?"
I explained the deal. She was a great help by reinforcing my thoughts about the election and money. In the end, we both decided it was best to turn down the offer. The one concern we both had was the Mayor might turn vindictive and close down the agency.
I called Tommy to explain what had happened and told him I had not taken the Mayor's offer. He said not to worry about the Mayor. Mayor Johnson is a good man. If he decides to apply some heat, we have his record on file.
"Oh, and Eve, something's came up and I need to speak with you right away. This is an out of agency situation and maybe we can talk about it at your apartment."
"Why not tell me now?" I inquired.
"Well, it's a delicate matter. I'll be there in an hour," he said and hung up.
Oh boy, another mystery for me to ponder. For Tommy to come to my place and on such short notice, it must be important. He said it wasn't about the agency so what could be so pressing?
See what's in store for Eve in Part Five
Kaylin
- 15.09.2020
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- Category:
- Straight Sex
Changing Professions Part Five
- 4 years ago
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Changing Professions Part Four
- 2 years ago
- 27
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