Charity Comes on the Road

Kevin's Story

As I sat in the lobby of my downtown St. Louis hotel waiting for her to arrive, I was sure that she would not. After all, we have never met in person; never even spoke to one another, until making these arrangements. I met Charity by sending an e-mail in response to her photo on her Literotica profile. It was a really artistic and beautiful black and white photo, I learned she took of herself, that gave her a very ghostly appearance, hence her Lit name ghost921. She responded and there began a yearlong exchange of e-mails about our individual sexual likes and dislikes. Today, we were scheduled to meet for the first time and I was nervous that she wouldn't show, that she would show and not be pleased, that she would show and I would not be pleased. I have never done anything like this and other then the rush of trying something new, the nerves were rattling.

I knew that Charity was tall at 5'10 with long red hair. I also knew she loved to wear high heels and that leather and vinyl were among her fetishes. She had also confided in me that cuming was not something that came easy to her. Yes, I knew a good deal about her looks and her sexuality but I had to admit I did not know her and likewise she did not know me. However, with all of that I was as excited as a teenager losing his virginity.

Charity's Story

Her I am sitting in my car in the garage of this downtown St Louis hotel, almost too paralyzed to get out and go meet Kevin. He was a man I knew little about other then he wrote very sexy e-mails and was willing to try most anything during sex, thought he admitted he was not a fan of things like asphyxiation, something I had told him I had tried and enjoyed. He also likes a bit of BDSM as I do and he floored me when he mentioned he would not mind being tied up by me. I had never before thought about being the "top" before and the idea took hold and for the next year or so we had continued to exchange e-mails titillating each other. Now he was in St Louis for business and he had mentioned he would like to get together and "see what happens". I agreed though now, I am obviously having additional thoughts. I am not prepared to go in there and see a look that says, "Oh your not what I thought you were, I wonder how long till I can dump you" or perhaps I might have the same thought. Oh well, you know what they say; "tis better to love and lose then never to love at all". And even though love is not a part of this you get me meaning. So I ambled out of the car and strolled into the lobby of the hotel.

Kevin's Story

"Charity, my god you're even better looking then I imagined."

Kevin said as Charity sauntered into the lobby, easily recognizable at her height, her black five-inch heels and her red hair. "Kevin, its great to finally meet you in person and you too are better then imagined, I'm glad we decided to meet."

Charity responded.

"Charity, lets go into the restaurant and enjoy a meal or a drink or both and catch up and chat for a while, is that ok with you?"

Charity nodded and they headed into the dinning room of the hotel. Once seated in a corner table Kevin began to admire the woman in front of him. She was elegant that was for sure, and in those heels and that black summer dress, it was hard not to begin to wonder what treats lay in store beneath the fabric. The neckline was scooped enough to give a hint to a delightful chest and her dress was short enough to allow her legs to mesmerize him. She was enchanting and very, very alluring, he would have to work on controlling himself or he might not be able to stand later.

"So Charity thanks for coming out to see me. I hope you drive wasn't too long or hard."

"Actually Kevin, I spent so much time thinking about this moment, what to say and wondering if we would like one another that the drive felt like a quick run to the corner store."

"Well that's good, lets order something so we can concentrate on getting to know one another."

They ordered dinner and while eating exchanged stories of their individual lives and other small talk. After dinner Kevin turned up the heat of the discussion by talking about the subject of some of their e-mails.

"Charity, you told me long ago that having orgasms or cuming was not something that came easy for you. Has that gotten any better or is it still a hit or miss kind of thing."

Charity was not prepared for this kind of open discussion, after all writing these thing on an e-mail to someone you really do not know is one thing, talking face to face with a man about sex was not something she had really ever did before.

"Well.... a....a...I have to admit I am not sure I can have this discussion, I mean I never have...I mean other then in an e-mail...give me a moment, Kevin, Okay?"

"Charity, I'm sorry. I did not mean to put you on the spot..."

"No, no, no don't apologize. I always knew that if we'd meet that we would most likely talk about those things we always wrote about and I came her knowing that...its not that I do not want to respond, I just need a moment to get "in the mood" if you will?"

"Well the reason I asked if purely self satisfying, I think I can get you to cum a bit easier, perhaps even more then once while having sex. So I thought I would see where you were and..."

"Kevin, yes, I still have a hard time reaching orgasm. We have tried a number of things, as you are aware, yet they remain a rare occurrence for me. As to weather I want to try with you is still under review, lets see how the night goes! OK?"

Kevin and Charity continued their conversation talking about their sex lives and fantasies thru desert and then some. They seemed to be clicking on all cylinders when while paying the tab, Kevin handed Charity a room key.

"That's the key to my room. I know you are thinking about what you might want to do and if you don't want to go up, we will still be friends and I would continue to want to exchange e-mails with you. However, we need to use our night well, so I said I could help you with your orgasm, and if you would like to do that I will tell you that you would have to do what I say when I say it."

"So, you'd want me to play the roll of a slave or sub?"

"Yes, in essence but not completely, in fact you could be the Dom, but you would still have to honor the rules in that scenario as well."

'What rules?"

"If you elect to go to my room, you will find a package on the bed -- the clothing inside will work just as well in a sub or Dom role. If you elect to stay and play it out you need to put on the clothing and if you are to be the sub, throw the security bar across the door so it stands a bit ajar, and I can enter without using my key. Then sit in the chair facing the door and wait for me. If you chose to be a Dom, and make me the sub, then put the "Do Not Disturb" sign on the door and close it. This way I will knock and ask permission to enter and you will then be in control of the night. There are some toys included that you might want to use as a Dom, and if you are the sub, I might use!"

"Sounds fair. I especially like the fact that it's my choice. I don't understand how acting as a Dom will help my orgasm, but if I do this then I guess I will have to wait and see, right?"

"Yes, I am going to go out on the back porch of the hotel and wait for thirty minutes. You can chose to go to the room and take the outfit and leave, select a role and follow the appropriate instructions, or come out to the back porch and join me and we will continue with our talks and enjoy the night air! It's all up to you, I wrote my room number on the back of the key for you."

"Kevin, I appreciate the options and I truly wonder which I will select."

"At any rate I will leave you now."

Kevin embraces Charity and kisses her on the lips as he hugs her.

"If I don't see you again at least I wanted to taste your lips and feel your body, I will go now."

And with that Kevin went off to the back porch of the hotel.

Charity spent several minutes in the lobby going over her options... She could tell be the creeping wetness between her legs and the hardness of her nipples that her body was interested in Kevin.

She was pretty sure her mind wanted to be with him as well. So after five minutes she headed in to the elevator and rode to the tenth floor and went to Kevin's room.

She spent a few minutes appreciating the view of the river from the window before picking up the package on the bed. Kevin had turned her on, of that there was less and less doubt as the moisture between her legs increased. She slipped her hand under the hem of her dress and sought out her opening and stroked her pussy lips though her panties seeking some relief. She had picked up the package. The "rules" instructed her to strip naked and put on the clothes in the package and to sit in the chair facing the door and wait for Kevin to return. In the package was a black leather garter belt, a pair of silk stockings, a black leather bra that would support her breasts but expose her nipples and a very short black leather skirt. She was instructed to keep her high heels on. She took her time changing, wanting to savor the moment and prolong the anticipation of Kevin's return. When she was done, she looked at herself in the full-length mirror in the bathroom. She looked very sexy, the skirt was so short it did not cover the bottom of her ass cheeks, and when she sat down, her pussy would be exposed. Later as she sat in the chair facing the door, she could not help but wonder what was in store for her but she was excited, her pussy was wet and it was all she could do to keep form touching herself again. She remembered the toys in the package and wondered which if any he might use, or if he would use them all. She looked down and saw that her nipples were as hard as ever and were beginning to ache, increasing her awareness of her sex and her growing desire.

She heard the door open and turned back in time to see Kevin step into the room with a smile on his face.

"Charity, thanks for staying, I see you chose to be the sub, very good. Should this time we spend together allow, perhaps you might try the Dom scene tomorrow?"

"Kevin, or should I say Master?"

"Lets stay with Kevin or Sir, I am not a serious Master type and that seems over the top to me. However, I do want you to have an "out" word, I've read about in and it is used in case I go too fast or am doing something you do not want, Okay?"

"I'd like that, what do we use?"

"Lets just say something we would not normally say like. I know let's use Missouri! Its not a word used during sex, its where we are and its easy to remember after all you live here."

"Yes, I am at your service, Kevin."

Looking her in the eyes, Kevin commanded that Charity spread her legs and expose her pussy to him. She hesitated and Kevin said.

" What I say when I say it or we will have to show you some discipline, young lady now spread your legs!"

She spread her legs, and when Kevin commanded her to open them further she did without pause. Kevin then sat down on the floor and stared into her pussy. Charity watched Kevin staring and felt her pussy begin to open and get wetter and wetter, and the longer Kevin stared the wetter she got till she felt it begin to leak out and cover her ass and drip down her legs. Still Kevin just stared. After another ten minutes Kevin said.

"I want you to begin to masturbate yourself with the fingers of you left hand, and don't hesitate or I will have to spank that wonderful ass of your."

Charity hesitated too long, after all she had never done that in front of a man or a woman before, it was a very private thing for her.

Kevin stood up and reached for her hands pulling her up from the chair then sitting down on the edge of the bed, pulling her over his knee.

"Kevin, I am sorry please don't spank me, please!"

"You had fair warning, I know this is hard but its best, if we are to make progress tonight. Now lay still and accept your punishment."

With those words Kevin pushed the edge of the skirt up and began to spank her ass. Using his left hand Kevin brought it down upon her left cheek and then her right in rapid succession, Red handprints began to emerge on Charity's white ass, and she began to squirm on Kevin lap as the blows fell one after the other. After ten on each cheek, Kevin rested and used his hand to massage her ass cheeks. She began to moan softly while continuing to squirm, seemingly trying to find Kevin's cock and impale herself upon it.

"Kevin, I need you. God I am so horny, I need you to make love to me! Please?"

Kevin stopped massaging her cheeks and slid his hand between her legs and felt the heat and wetness of her pussy. He knew that the spanking had turned her on and that more spanking would just excite her even more. He knew that if he was to help her get off more then once he had to not give in to her yet.

"I felt your heat, I judged how wet your pussy was and you are not ready. When you're ready you will let me know by how you beg me."

With that Kevin resumed spanking her, giving each cheek another ten slaps. When he was done he pushed her up and sat her back in the chair, again telling her to spread her legs. Charity obeyed immediately and continued to moan and move her body; she was as turned on as she had ever been. She hadn't been this wet, been this hot in a long time and she needed to have Kevin inside of her. Once again she asked Kevin to make love to her, and he refused saying.

"You still have not learned to beg."

Kevin went into the package and removed a long leather belt with buckles on each end. He came to her and placed the belt around her neck with a buckle and about two feet of leather to either side of her head.

"I want you to put your hands behind you head, with your elbows sticking out to the side."

She did as she was told and he fastened the ends of the belt around her wrists.

"I am not real fond of 'asphyxiation' but with this belt if you try to move your hands away for any reason, the belt will tighten around your neck until you return your hands where I put them. Do you understand? Are you ok with this?"

Charity was a bit frightened but at the same time excited. She knew he was stretching his own likes to include something she liked and was pleased to allow it.

"Please, Sir, just keep an eye on me, just to be safe! OK?"

Kevin nodded. He then took a pair of nipple clips and after sucking and pulling on her right nipple, placed the clamp on the swollen nub and tightened it down. Working quickly he repeated the process on her other tit and she was enveloped in a delicious pain that forced her hands away from her head, choking her, the excitement was wonderful and she felt as if she could cum just sitting there, but she eased her hands back relieving the pressure on her throat and thanked Kevin for his gifts.

Then Kevin crawled between her legs and brought his face square to her pussy. She felt his breath caressing her and she gasped as another level of pleasure coursed through her body, mixing with the pain from her pinched nipples and mounting ever higher. Kevin then began to "eat" her, she knew how much Kevin liked this, and he had spoken of his love for eating women many times in her e-mails. Good god he knew what he was doing, it was wonderful. He had sucked the left lip of her pussy into his mouth and took it between his teeth and pulled gently on it, then repeated this with the other lip. By now her pussy was on fire and she again said.

"Please, Kevin, Please. I need to have you inside me, please put it inside me, I need to cum, Sir, I am going to cum, I can not hold it back."

Kevin ignored her and continued his assault on her pussy. He grabbed the calves of her legs and moved her legs over his shoulders, enjoying the feeling of her shoe heels digging into his back, taking his tongue he licked the outline of her pussy and them began to pump his tongue in and out or her, like a small cock. The effect was immediate and she felt her orgasm coming, and she could not stop it, it was powerful almost causing her to black out. She was writhing in ecstasy as Kevin's tongue found her clit and his lips surrounded it and sucked in hard into his mouth -- that was it, she exploded again and again cuming into Kevin's mouth so hard that he had trouble swallowing it all down. As she felt her orgasm dying Kevin stopped his assault and again stood and reached for chain between her breasts, attached to the nipple clips pulling her up while he sat down on the bed and tossed her over his knees.

"I never said you were allowed to cum, did I not tell you that you were to do what I said?"

"God Kevin you were so good, your tongue was everywhere, I had to cum, and it was impossible to stop myself."

Charity whispered in her post orgasmic state. Her tits ached from the rough way he pulled her up but that fire only increased the power of her orgasm. Kevin then said.

"As my slave you are to do only what you are told, you are to be punished, hopefully it will help you learn."

With that Kevin again began to spank her ass, this time with his right hand. As he was administering the spanking he used his left hand to penetrate her pussy and finger fuck her. Charity was once again on the trail to orgasm, a trail she had never been on this soon after orgasming. She felt his hand stinging her ass cheeks and his fingers plowing in and out of her hot wet pussy and knew she would come again soon.

"Do not compound this by cuming again, I do not allow you to do so."

"Kevin I ....aahhh. do... know...if I ....cccccan ssstop ittt...iiiiit fffeels sooooooo good."

"You will obey me or suffer the consequences."

She fought the urge to cum, wanting so much to please this man who had brought her to such heights. She had never felt this good, so she did her best to hold back the rising tide and found some success. However, when Kevin slipped his thumb into her anus, she almost lost it. Thankfully she was strong enough to control it and was able to stop the orgasm long enough for Kevin to finish with the spanking.

Kevin removed his shirt and pants and he sat down to remove his socks and shoes, then had Christy kneel in from of him, her hands still around her neck, her tits still imprisoned by the clamps and told her.

"Use your mouth and teeth and remove my shorts."

Charity complied and as she struggled to pull them down and somehow get the waistband over his hard cock, she could not help but smell his arousal. Having finally succeeded, she knelt on the floor and looked straight at his cock. It was beautiful to her, about six or seven inches, circumcised and hard. She could she some precut leaking form the tip and started to lick it off with her tongue, when she stopped immediately remembering her need to be instructed. She looked up at Kevin and said.

"Sir, may I take your penis in my mouth and suck it for you?"

Kevin responded.

"It's my cock, a penis is a name for a male organ, and my cock is a tool to fuck you."

"May I suck your cccock, Kevin?"

Kevin nodded and Charity engulfed his cock in on move. She took all of him, right down to his balls, and then she rose up and began to slide up and down using her tongue to caress his tool as she did so. She was lost in pleasure when his hands came down and pulled her face away from his cock.

Kevin took her and laid her on her back on the bed so that her head rested on the pillow. None of this was any easier for Kevin; his cock was rock hard and having to hold himself back while she administered a very good blowjob. Each time he looked at her he felt as though his cock grew larger and harder, it was almost painful for him, he knew it all had to end soon. As soon as she was ready, she would let him know. He let her rest for a few moments before he began. He remembered how much she indicated that she liked her tits played with so he bent over and removed the clamps for her nipples, taking her left nipple between his teeth and gently bit down on it before sucking it hard into his mouth. Christy never thought she could reach this level of excitement, but as Kevin continued his assault on her tits, still reeling from the pain of the blood flowing back into her nipples she whimpered over and over again, as mini orgasms continued to crash through her. She stopped caring about permission, did not worry about her ass being spanked, only her orgasms mattered. With only the top half of her tits available with the leather bra still encasing her globes, so he took a moment and undid the front clasp and moved the cups to the side. His hand had found her right tit and was grabbing it with his hands and kneading it like a tub of putty. Her tits were not large, more a B cup then a C, and definitely not an A, they were exactly the kind that Kevin liked. Her nipples, when stimulated were over a quarter inch long and as hard as his cock. He spent a good deal of time on her tits, switching back and forth with his mouth and hand, balancing his ministrations. Her tits were swelling and turning red and Charity was once again closing in on a major orgasm. This time she said.