The Traveling Worker Ch. 10

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Final--Diamond invites Tim for a nightcap.
3.2k words
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Part 10 of the 12 part series

Updated 09/22/2022
Created 09/24/2008
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TimWLy
TimWLy
7 Followers

By the end of the second day, I was feeling much better, but just ready to get the trip over with, but there was more work to be done, and workshops to be attended and staffed.

I assisted with registrations, and also with note taking, but ultimately the third day was rather uneventful. That is until Diamond and I ended up having Dinner that night which lead to very interesting conversation.

Diamond and I really were like close friends, and could talk about anything, but I never considered her for the type to want a massage, or to even be someone I would hit on, but after seeing that she would rush to my aid and make sure that I was ok, and also keep secrets for me, I had a whole new level of respect for her.

I also found that I would end up having to pay back some form of debt before that night was over as well.

Diamond and I went to one of the hotels restaurants after the final session was over, and just had a quick dinner with a few other patrons, and essentially were just shooting the breeze, about work, kids, about being ready to head home, and making sure that the rest of the conference goes well, but then the conversation turned when she asked if I would like to meet her in her hotel room for a night cap.

This was a surprise to me, just because we had never approached this level before, and we had always been respectable, and to some degree, she even knows some of my dirty laundry.

I gladly accepted, and just figured I would try to keep it friendly, because I didn't want to lose a good friend, or the level of respect which we had for each other.

Considering that her and I have worked together, and we talk everyday, I know my mind has wandered on a few things before, but now that it was right there in front of me, I wasn't exactly sure what was going to happen, I just knew that I couldn't let the other things that have happened on this trip get in the way of spending time with her, because she is something special, and different from the rest of the group. Besides being the oldest, she is also the easiest one to share and communicate with on a different level, and that is one of those things I cherish about her.

After walking around and speaking with some of the participants, and staff members, I stop by my room, and by this time it's about 8:30 pm in the evening, and I rang Diamond to see what she had in mind.

"Hey Diamond, It's Tim"

"I wanted to find out what time you wanted me to stop by, because that wasn't something we discussed earlier."

"Well, Give me about 30 minutes, and you and I can meet up, so we can hang out some more, is that cool?" Was the response I received from Diamond on the other end of the phone.

"That's fine with me, and I will see you then."

With that we hung up the phone, and I went about preparing to hang out with her, and not being sure what to expect, I grabbed a quick shower and just put on some slacks and a polo shirt, to ensure that I was comfortable, but presentable.

Next thing I knew Diamond was there at my door ready to go for a stroll, and we decided to head back to her room, and since we were on the same floor, she went the short route, so that we couldn't be seen by others.

Arriving back to her room, she brought me in, and we went out to the balcony area, where there was a table and chairs for us to relax, and sit and talk, and although all of the rooms have the balcony area, she had a corner room, which gave her balcony more space, and also a view of the river down below.

Sitting down to the table, I noticed that there had been fruits spread out on the table, and we began to sample some of them, just listening to the street noise and the river down below, and just enjoying the beautiful night given to us by nature.

Just as I started to really zone out and enjoy the feeling of being there, I was broken out of my own thoughts by the sound of Diamond beginning to speak by her saying:

"Tim, you know you gave us all quite a scare yesterday, and part of me inviting you up here tonight is to make sure you are ok, because the boss wanted to make sure, but also for my own selfish reasons."

"Diamond, I am fine, and you know I was pretty scared there myself for a while, and I really appreciate you and Yvette looking in on me, without you two, I wouldn't have gotten through yesterday." Was my response back to her.

"So you can let everyone know that yes I am ok, and after getting through the workshops today, I am feeling much stronger." I continued.

"I am glad to hear that, she says, because I have heard rumors from some of the ladies about you giving massages, and now I am going to be selfish and ask for one of my own." She finishes with a low tone and a hint of mischief in her voice.

"Oh, is that what all of this is about?" I say.

"Yes" is her simple response

With that I feel her beginning to run her toes over my calf and I can feel her staring directly into my eyes,, as if burning a hole into my soul, and slowly and surely I take one of the pieces of peach off of the tray, stick it in my mouth, and begin to slide it over my lips and deeper into my mouth, as if sucking the juices out of it.

With this display, her foot stops moving, and I can tell she likes what I have done, and I repeat the display with a piece of pineapple, then a piece of strawberry.

With the last piece of fruit I hear a small gasp escape her lips, and I can now tell that the tide is turning, and I have to quickly capitalize, or else I will show my hand, which is a huge bulge in my slacks.

With that I stand very slowly, move over to where she is seated and begin to touch her softly yet firmly, and ensure that I take my time.

Enjoying the night's coolness, I begin to touch her shoulders and her neck, and her skin is very warm and very smooth, and even without the massage oils that I have used, my fingers glide over her skin effortlessly.

Then adding a twist, I drizzle some of the different juices over her shoulders , just enough to let her feel the drops, and I begin to lick from her left shoulder, to her right, going across the back of her neck, moving her long hair to the top of her head, and nibbling on her ear lobes along the way.

As I only taste the fragrance of her skin, I go back to lightly massaging her shoulders, and slowly I push the straps of her dress down off her shoulders, letting them rest on her biceps.

From what I was able to tell, her dress was a one piece backless number, and because her hair was so long, she didn't have to worry about showing to much skin.

As much as I wanted to continue the massage right there on the balcony, I had something even more special planned for Diamond, and standing her up, I spin her to me, and putting her dress in order, we stood there looking at each other and holding hands, trying to decide if we were really going to make that move.

I pulled her into me, so that we could feel the warmth of each other, and smelling her womanly scent, and feeling her soft body against mine, helped me make up my mind, and I turned her face up to mine and we kissed for the first time, and it was a soft warm kiss, nothing hard about it, just enough to show that the passion was growing and that we were both there in the moment.

Then as if I knew what her room was set up like, and as if she knew what I was asking her for, we both headed right into the living room space, but we weren't going to be watching TV.

We kicked off our shoes, and I took off my shirt, and I stood behind her in front of the full length mirror, and asked her to undress for me.

She looked back as if to ask if I was sure, and I massaged her shoulders to let her know that I was going to be right here with her, and I whispered to her to describe it for me.

She slowly started with confidence in her voice:

"First I am going to reach down under my dress and roll down my panty hose, all the way down to my feet."

As she did this, she bent over right in front of me, and pushed her ass right into my hardening cock, and I gave it a hard shove right into her ass to show her that I wasn't backing away.

"Then, if you could help me, unsnap this one hook on this dress, I can take the straps off my shoulders."

Was the request I saw, but didn't hear, because she was bending her arms behind her to grab at my hands to put them on the hook which I needed to unfasten.

With one quick motion the hook was undone, and slowly I was rubbing my finger tips between her shoulder blades, and it seems her back was a very sensitive area for her, and it was continuing to get her aroused.

I couldn't keep the advantage for long though, because she then, shrugged off the shoulder straps, and let the dress slide to the floor, and oh my goodness did I want to kiss nibble or lick that trail right down to the carpet.

"So, Diamond, what do you see when you look in the mirror right now?"

"I see me in my bra and panties, and you in your slacks, and I feel like you are over dressed."

"Do you like what you see?" I continue with my line of questions, trying to decide how far I should take it.

"Yes."

The whole time we were standing there at the mirror, I was rubbing her shoulders and her back, making sure that she got the massage she asked for, and then as she got down to her bra and panties, she knew she had the advantage, so she pushed herself into me, and wrapped herself into my arms, and began running my hands up and down her belly.

"Mmmm, Diamond that feels nice, you should stop before you cause my cock to get harder and I come all over myself."

With that statement, she begins to grind her ass up and down on my cock, and I begin to run my pointer finger and thumbs over her nipples, and they are like little nubs, which you can feel the sharp points at the end of them to suck on, and she hasn't even gotten out of her bra yet.

I then go ahead and un hook her bra strap, and slide it off her shoulders, and she also lets that puddle at her feet, and then she turns to me and kisses me with a fiery passion, and unfastens my belt and pants, and seeing how hard I am, she begins to stroke me lightly knowing that I can explode at any moment.

Letting me slide out of my pants we both stand there looking over each other, and then she walks away toward the bedroom, and thinking I have the upper hand, I don't follow, because this will give me a chance to calm down as well.

We play the game of cat and mouse for at least 10 minutes, and no one moves, but since my services have been requested, I break first, and go toward the bedroom to see what I can do.

"So Diamond I hear you have requested my services for a massage, what can I do for you?"

"Well, a simple foot rub is all I am good for now, because I just took care of a little problem I was having."

Thinking to myself she can't be serious, I proceed with giving her the slowest and most sensual foot rub I can, trying to rub all the tension away, because with the way this week has gone; I know that she has been under plenty of stress.

Knowing I can give foot rubs for hours, I just continue to alternate from toes to feet, to arches to heels, allowing for her to relax, and I am trying to see if there is any visible reaction.

Besides a couple of moans of pleasure, not much came in the way of visible reaction, so I decide to turn up the heat a little, to see if I can push the envelope.

I begin to massage her legs, and her calves trying to ensure that the relaxation spreads throughout her body, but also trying to get closer to the prize, from my point of view.

"Diamond please let me know if you have had enough, or if you want me to go further, or how you are feeling." Was my response, after the standard hour long massage went past.

"Tim, I can see why the ladies rave about your hands, because it has been hell holding out on you for the last hour, and trying to not give myself an orgasm, just by playing with my nipples." Was Diamonds response back.

"So you have been turned on by what I have been doing, but you didn't want to show it?"

Why not?"

"Well Tim, it kind of hurt my feelings that you had your chance to come in here and go for it with me, but you didn't take it, you waited for me to do something, and then nothing happened, so I kind of lost the urge."

"Then when you touched me, it all came back, but I guess pride got in the way." Was Diamond's answer.

I curled up next to diamond and kissed her softly, and before you knew it the passion was building again, but I just wanted her to know:

"Diamond, you and I have been friends for a long time, and we know a lot about each other, so I have a lot of respect for you, and I wouldn't want to do something to mess that up."

"Tim I agree, but you have to also understand, unlike everyone else, I have had a crush on you for a long time."

With that revelation, I threw caution to the wind, and just made sure that I cherished every moment, and gave every piece of myself to Diamond, so that we could enjoy what we had.

I slid in between her legs, and as she spread herself open, I could smell her arousal, and could feel how fat her clit had gotten, and the fact that she had gotten so wet, and my cock was going to soon be invading that space, had me dripping with pre-cum, and harder than granite it felt to me, and hotter than the sun on an August day in Houston.

I took my time, inching closer, making her practically beg for it, giving her mini orgasms as I inched in deeper and deeper, holding her down on the bed, as I slid all the way home.

Then pinning her hands down on the bed, her legs wrapped around me, slowly we began to grind together and her clit and my pelvic bone would grind together, and she would shiver and whimper with delight.

Then finally it happened, she came it one short spasm, then as I let her arms go, she held on to me with a long spasm which caused her body to clinch down on mine, and to clinch my hard member inside her, and it felt good, that it was tight, wet and warm, and all I could do was rock back and forth in short thrust until she relaxed.

Then after that first big orgasm, she rolled me over, because she was ready to go harder and faster, and we were going to make sure we both went all the way.

"With no mischief, no pain, no remorse in her voice she announced, I am going to ride you hard, and you are going to get the fucking ride of a life time."

There was nothing I could say, nothing I could do, I just held on, and even though she started out slowly, as she found a rhythm, we both began panting, and trying to make sure we didn't pass out from a loss of oxygen.

I could feel her wetness squishing out of her and coating my cock with every downward thrust, and it felt delicious.

"Oh yeah, come on baby, you want this cock deep inside you, ride me harder and faster." Was the only response I could come up with, as I could tell we were both getting tired, but I was no where near coming.

With this Diamond changed her technique, she went slower, not faster, and began to really grind her hips with every stroke.

I then reached up and felt her breast for the first time all night, and all I can say is wow, why didn't I do this earlier, they were perfect, a D cup, hefty but firm, and they seem to do the ticket for her as well, because as I twisted and pinched her nipples, she moaned out another orgasm, and as she came down squeezing my hard shaft inside her and just holding me there, I could feel my come starting to boil up inside me.

She then leaned over and teased me with her nipples, and allowed for me to play with them with my tongue, and that was it, hearing her moans sent me over the edge, and with two thrust upward, and her thrusting back down on me, I came hard, and deep inside her.

With that, she collapsed on top of me, and we kissed a soft yet warm kiss, and it was like we didn't want to let go.

Knowing that this was going to be the last night before we were to fly back home, we enjoyed a late night snack, and also enjoyed each other one more time before I headed back to my room for the night.

The next day was uneventful, with breakout sessions and the closing ceremonies, and smiles and handshakes all around, for what turned out to be a very successful conference, but a flight home for me on the other hand, just means I would end up having to return to my day job, at least now I have people I feel I can always count on.


I hope you have enjoyed the traveling worker in Louisville, and although completely made up, it was still a joy to write.
Please stay tuned for the traveling worker going to Baltimore.

TimWLy
TimWLy
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