Chapter 5: Molly the whore

Molly’s role as whore; but, is it enough?

I drove to the street where we had arranged to meet. There, under a lamppost, I saw a woman standing with one leg bent and her back leaning against the lamppost. Fortunately, this time there didn’t seem to be any risk of confusing me, I thought. There was no one on the street, although I noticed some isolated lights in an office in the area, possibly some maintenance or IT team doing work they couldn’t do on a daily basis.

I slowly drove up to her, taking in her appearance. Although she had disguised herself as Molly, as before, with red hair and green contact lenses, her make-up was much more exaggerated, more ‘whorish’; she had also put on long false eyelashes.

As for her clothes, she was wearing a very short, tight leather skirt, which came barely to mid-thigh, black stockings, and black high-heeled shoes. On top, she wore a semi-transparent blouse that had been tied in a knot at her navel, with a deep neckline that showed she wasn’t wearing a bra. She carried a small handbag slung over her shoulder.

As always, she was very attractive, though in a totally different and more vulgar style than on our hotel dates.

I pulled up in front of her, rolled down the window, and addressed her, “Hi.”

She walked over, leaned over, and stuck her head through the window, showing me more of her breasts through the cleavage, “Hey, handsome boy, want anything?”

An intense smell of cheap, violet-scented perfume wafted in through the car window as she stuck her head in.

“I was looking for a little company tonight,” I answered.

“Perfect; I can provide all the fun and companionship you need. Do you want anything special?”

“No, I wasn’t thinking of anything in particular. Just the company of someone pretty like you.”

“I charge 50 for a blowjob, 100 for a ‘full’, and 400 for the whole night. If you want it without a condom, it’s 50% more, except for the night, which is only 100 more. You pay for the room. And I warn you, I charge in advance.”

“I’d like to spend the whole night with you.”

“Then go ahead,” he said, opening the door and sitting in the passenger seat, “There’s a motel nearby. I’ll guide you. My name is Molly.”

“I’m Buck.”

I drove to the nearby motel, guided by her instructions. Once there, I parked the car, went to the reception while she stayed in the car, and booked a room.

We went to the room. As soon as I closed and locked the door, she turned to me and said, “400 in advance.”

Although I didn’t know what it would cost, I had prepared money for the night, and I gave her what she asked for. She pocketed the money, and then she took a packet of condoms out of her purse and put it on the bedside table next to the bed.

When I saw it, I got stuck and said, “I was thinking of doing it without a condom.”

“Well, that’s 100 more.”

I didn’t have that much money on me. I wondered if Moly would be able to demand that I wear a condom. I was amazed at her ability to get into the role and also at her ability to play with me and tease me.

I mumbled, “I’m sorry, I don’t have that kind of money on me. Couldn’t you make an exception?”

“I don’t like to make exceptions. Everyone wants discounts and exceptions. And I take a risk of catching a disease.”

I didn’t know how to get out of the jam. I could see how Mary’s eyes reflected her amusement with the game and how she made me “sweat it out” to be with her.

Suddenly, I remembered a general medical check-up that had been given to all the employees of our company.

I said to Mary, “Molly, I have a recent medical examination that I can show you. You’ll be able to see that I don’t have any diseases. Would you let me do it without a condom?”

“Well, I like you; you seem like a nice person, Buck. Show me that report, and we’ll do it without a condom.”

I breathed a sigh of relief. I showed her on the cell phone the report, and she, after reviewing it, put the condom packet in her purse, walked over to me, and said, “Now, get ready to have a good time.”

She kneeled down in front of me, unfastened my belt, and pulled down my trousers and pants.

She took my cock in her hand and said, “You have a nice big cock, Buck. I think we can have a good time tonight.”

She moved her head closer and took the tip of my cock into her mouth. Her lips, painted a shuddering red, stood out, enveloping my cock.

Slowly, she lowered her head and leisurely slipped my cock into her mouth.

It was a delicious feeling, but after having my cock locked in the cock cage for a week, it was even better.

Gradually, she began to bob her head up and down, taking more and more of my cock in, until it was touching the entrance to her throat. At the same time, she fiddled with her tongue along the underside of my cock and along the frenulum, giving me untold pleasure.

She continued to suck my cock, running her lips up and down the length, sometimes quickly, sometimes slowly, while keeping her hand on the base, preventing me from taking it further into her mouth or varying the speed. My cock was covered in saliva, shiny, red, and fully erect, almost to the point of aching.

My excitement was growing more and more. I had closed my eyes and let myself be carried away by the sensations and the pleasure Mary’s mouth was giving me, until finally I couldn’t hold on any longer.

I felt my testicles contracting, my cock throbbing, and a stream of semen began to run down my urethra and gush, like a volcanic eruption, into Mary’s mouth, who, noticing the beginning of my ejaculation, held still, letting her mouth fill with my semen. I almost lost my balance and had to rest my hands on Mary’s shoulders.

Although it must have been seconds, it felt like many minutes passed without the flow of semen letting up. All the cum that had accumulated in my testicles during a week of excitement and desire was gushing out uncontrollably.

As I finished, I looked down at Mary, who swallowed the remaining cum in her mouth, looked up at me, and said, “Wow, tiger, what a release. Has it been a long time since you’ve been with a woman?”

“Only a week, but it seemed like a long time to me.”

“Well, we’ll have to make up for lost time, Buck. You paid me for one night, and I’ll make sure you get your money’s worth.”

She kicked off my shoes and removed my trousers and briefs. Then, standing up, she unbuttoned and removed my shirt.

She began stroking my torso and fiddling with my nipples, “You have a pretty nice body, tiger. Come to bed.”

She led me by the hand to the bed, where I lay down. She began to undress, taking off her blouse, for which she only had to undo the knot, and revealing her lovely breasts; then unzipping her skirt and removing the skirt and thong she was wearing; finally, she took off her shoes and climbed onto the bed.

Kneeling between my legs, she continued to stroke me all over my body, caressing the areas she knew turned me on the most, until my cock started to get erect again.

She took it into her mouth, sucked it until it was fully erect, moved forward until she was on her knees at the level of my cock, guided it until the tip was at the opening of her pussy, and, excruciatingly slowly, moved down, inserting my cock into her hot, wet sex.

Once she had descended until she was fully impaled on my cock, our pubes in contact, she began to move up and down, equally unbearably slowly. My hands went to caress her hips and her thighs until they went to her breasts, which were in front of me, swaying with her movement and, above all, with her increasingly agitated breathing.

I fondled her breasts with relish, enjoying their touch and softness, and at one point I grasped her erect nipples with the index finger and thumb of my hands. I kept my hands fixed on her nipples, so that as she moved up and down on my cock, she stretched her own breasts up and down, increasing her arousal. She responded by pinching my nipples hard, already lost in her pleasure and arousal.

Her pace quickened, and the excitement quickened as both our breaths quickened. We gasped and moaned louder and louder.

Finally, we both reached orgasm simultaneously, something that doesn’t happen very often, despite what the ‘urban legends’ say.

I was exhausted, but she kept moving on me, linking the first orgasm with several others, squeezing out her pleasure until she fell exhausted on top of me.

After a while of catching her breath, she lay down next to me, saying, “Wow, Buck, it’s been so long since I’ve had an orgasm with any of my clients; you’re fantastic.”

We lay there cuddling, and I wasn’t even aware of when I fell asleep. The next morning, I woke up to her sucking my cock, which had the usual morning erection.

That totally woke me up. When she saw that I was awake, she got on all fours, with her ass towards me. I needed no further invitation. I kneeled behind her, caressed her vagina, checking that it was wet, placed my cock at the opening of her sex, and slowly pushed myself into her vagina. I grabbed her hips and moved my hips back and forth, fucking her hard, sliding my cock into her soft opening.

I had before me the wonderful sight of her beautiful back and her shapely buttocks.

Before long, I felt my orgasm approaching. I pushed all the way in, held still, and felt the semen run down my cock and be expelled, adding more fluids to Mary’s already soaking wet pussy.

I kept pumping some more until Mary climaxed as well. Then I rested my torso on her back, brought one hand to her clit and the other to her breasts, and caressed and stimulated her until she came again.

Exhausted and sweaty, we collapsed on the bed, still joined, with my cock in her vagina.

I kissed the back of her neck and her ears, telling her, “You’re wonderful.”

After showering and soaping each other, I drove Mary to where we had met the night before to pick up her car.

As she got out of my car to go to hers, she said, winking at me, “That was great, Buck. If I’m free next Saturday, I can book it for you, and I won’t charge you extra for doing it without a condom.”

As I drove home, I thought about Mary’s extraordinary ability to put herself into a role. I remembered that when she was at university, she was in a theatre group formed by the students, and she was really good at it. Not only did she prepare and study the roles conscientiously, but she immersed herself in them, almost becoming the characters.

At home, while we were having breakfast, we talked about how we had spent the night. We both had a lot of fun and enjoyed ourselves enormously. We decided to do it again.

We continued with the rhythm as in the previous weeks: me locked in the cock cage, continually teased and denied, while providing her with daily orgasms, and on Friday nights, playing our roles, in this case not a couple of strangers but a client and a prostitute, and having extraordinary sex.

As in previous weeks, Mary occasionally took pity on me and allowed me to orgasm when she saw that I was too desperate, so that I wouldn’t have to wait until the weekend, and also because she felt like it, she told me.

One afternoon, as we were talking about plans for the following weekend, I noticed that she was not as enthusiastic as she had been at other times, so I asked her, “What’s the matter with you? You don’t feel like going on, do you? Are you tired?”

“Not exactly. I’m enjoying it a lot, but, I don’t know, maybe it’s that we people put a lot of enthusiasm into our fantasies, and then, when we try to put them into practice, it’s never the same as we had imagined. Maybe that enthusiasm makes the result, even if it’s very good, a bit disappointing.”.

“Well, don’t worry; I understand you; it’s been a bit like that for me. You think of a fantasy, but then it can’t be the same in real life.”

“Yes? What went wrong with your fantasy? I thought the teasing and waiting game locked in the cock cage was exactly what you were hoping for.”

“Well, oddly enough, in my fantasy, I saw myself as desperate to cum, on the verge of coming, and not getting it for a long time. When you let me cum during the week, on the one hand, I was so desperate that I wanted it with all my heart, but on the other hand, in my fantasy, you were inflexible and never let me cum, even going more than a week without being able to do it.”

“I’m sorry,” said Mary contritely, “I thought I was doing well, but I thought you suffered too much when I teased you and you couldn’t come. I was incapable of seeing you suffer. I became afraid you would have a heart attack because you were so excited. But I promise, I will do my best to make your fantasy as good as possible. I will be strict. I’m thinking there are these little safe deposit boxes that have a timer that can be programmed to open only after a certain amount of time. We can buy one to hold the key to your cock cage, and that way, even if I want to, I can’t release you.”

“Thank you. You are wonderful. I can’t think of a better wife than you. And what could we do to enhance your fantasy?”

“Well, I don’t know,” Mary replied reluctantly.

“Tell me anything; I swear I’ll do anything. I want you to be happy.”

“I don’t dare tell you. I think it’s something I’ve got in there. I can’t ask you...”

“Ask me for anything; in advance, I promise I will. Tell me what you feel.”

“Now that you’ve promised, it’s harder for me to say it...”

“Please, Mary. Share it with me.”

“You see, when we play at being two strangers and we’re in bed, I can’t help but know it’s you. Despite the disguises, I see your face and your body. Not only that, we know each other very well. I know what turns you on, where to touch you, and how you’ll react. You caress me where you know I like it; you try your best to make me enjoy it as much as possible; you have your way with me, loving, caring, and concerned about me. That’s all great, and I enjoy it very much, but it’s not my fantasy of making love to a stranger, not knowing how the other person will react, exploring unfamiliar territory, with someone who treats you differently than you treat me, Charley.”