Summer Sugar

"It's okay baby, just relax and enjoy the afterglow. I didn't hurt you, did I?" Shelly asked.

Since the first moments this was the first time I again thought of any pain or discomfort something that I'd been warned by so many would come from losing one's virginity. But I didn't feel anything uncomfortable at all up to that point. Now it was simply the unyielding firmness that was still inside me, that was starting to annoy me a little, and I let Shelly know.

"I understand," she said as she sat up and began to slowly withdraw it from me. "A man eventually goes soft after he cums" she replied, "So you shouldn't experience anything like this in the future. Unless, of course, you use a toy," she said with a smile, all the while removing the strap on from her body.

"So, no pain or discomfort at all?" she asked again.

"Mmmm, just some light tingling and a strange, almost empty feeling," I told her.

"Good," she said as she began examining the glistening cock, first with her eyes and then with her tongue.

The sight of her lightly licking around the toy's shaft stirred more sensual feelings in me, especially as she looked at me while doing it. I sat up, pulling myself closer to her face and placed my mouth on the opposite side of the cock from her. She made an "mmmm" sound as we both slowly slid our lips up and down the cock in unison, looking at one another lovingly. She then backed away and turned the cockhead to me, pressing it against my lips. I could smell myself on the toy.

I opened my mouth as she slid the cock across my tongue, gently moving it in and out of my mouth before removing it and placing it in her own, again simulating a blowjob. I placed my hand between her legs and felt her very wet pussy, and felt a cool damp puddle underneath her, on the back of my hand. I placed two fingers at her opening as she leaned back just a little. My fingers slid in easily, the pad of my hand against her clit. She then placed the cock to the side and leaned forward for more kisses where I could taste myself while softly moving my fingers inside her, as well as in and out.

"Let's get comfortable," Shelly said.

I placed one hand on her shoulder while removing my fingers from her pussy. I brought them up and lightly ran them across her lips before pressing the digits into her mouth, where she sensually sucked her juices from them. I immediately, though passionately, attacked her mouth with mine, licking her flavor from her lips and mouth. As always, Shelly tasted so sweet. The force of my "attack" had caused her to fall back as I stayed attached. Our breasts pressed together and I felt both their warmth and her aroused nipples. One of my thighs was between her legs, laying against her warm, wet pussy as I made little movements to rub mine on the top of her thigh.

Breaking our kiss and catching our respective breaths, Shelly then said almost in a whisper, "I've never encountered anyone quite like you Monica. I love you baby. You're going to make someone very happy one day."

Again, I won't bore you with the details when Jason and I got together a few weeks later, but it's safe to say, with tongue firmly planted in cheek, but it was anticlimactic given what Shelly and I experienced together. And while I was fond of Jason, I realized immediately afterwards I wasn't in love with him, and that made all the difference in the world. Not that it was unpleasant, there was the usual fumbling and inadvertent collisions as two unfamiliar people seeking intimacy together for the first time are bound to have, but I can honestly say it was satisfying. For both of us. And I strongly believe that was only possible through Shelly's loving guidance.

And Jason and I continued to date, and occasionally had sex. He got better at pleasing me over time, and I'd like to think I began to understand what men, in general, liked while realizing everyone has their differences. It was a learning experience, and I came away from that period in my life understanding one could have sex simply for pleasure, without becoming a slut.

Moving forward several years I'm ready to implement my plan. After reviewing a number of the better known and, from research, the more reputable sites, I decided to lay out a few rules and guidelines. First, I needed to establish an exit strategy. I was going to use my personal assets to pay for my degree. I wasn't interested in material things, other than cash, so compensation should not be in the form of clothes, jewelry, fashion accessories, etc.,. I had reliable transportation so I didn't need a new car. Once I had covered my graduate expenses or graduated, whichever occurred first, I would no longer make myself available - as a sugar baby that is. I still have a reasonably high (I think) sex drive, and I'd want to pursue a normal relationship with others - whatever that means right?

But back to my new project. I signed up on what appeared to be the best site for seeking such an arrangement (hint, hint) using my middle name (Leigh), uploaded several tasteful photos, and a little narrative about myself and my expectations. I even included I was bisexual, in case there were some sugar mommas out there. The respondents would know there would be no sexual contact on the first "date." We'd meet at a location of my choosing, typically a restaurant where we'd begin our conversation over coffee or drinks. Depending on how the first thirty minutes or so went, if mutually agreed to we'd order dinner and continue getting to know one another. However, I would insist on being compensated for my time in the amount of $200 for the evening before ordering, or I'd leave - this did happen on more than one occasion. A couple gentleman hesitated at first, but as I rose from the table, they quickly laid an envelope on the table, typically wrapped in a dinner napkin. During a number of encounters the "no sex on the first date" rule was difficult to adhere to because the guy was so damn attractive and sexy, but I can report that I held firm in my convictions. But what followed those dates was some of the best "solo sex" I ever gave myself.

I had multiple responses from males in the first hour, and only a few were serious enough to warrant a reply. Most had no picture in their profiles and only one of those was interesting enough that I replied back requesting a recent picture or I was going to block him. First dates always occurred on Tuesdays or Wednesdays, and second dates where we became intimate were reserved for Friday thru Sunday. And of course, any travel could occur any time afterwards once we became comfortable with each other.

Any follow on dates were $1500.00 each occasion, and there were several gentlemen who were interested in continuing a longterm monogamous relationship with a monthly allowance. I understood the financial reasoning behind each offer, and was naturally flattered they wanted a continuing liaison. It meant they enjoyed what they saw, felt and tasted, and for the most part I enjoyed the same. And while each one I fucked were fun in their own way, they just didn't have the "it" that would cause me to forego all others who seemed interesting. The good news? My savings account was growing exponentially with the fun and experience I was getting.

My favorite had to be a response I received back almost immediately from an attractive guy, and after a few brief messages back and forth, we took our discussion offline. First it was via email, and once comfortable a few weeks later we exchanged phone numbers and began texting, until I eventually asked him to please call.

During our first date I learned "Steve" worked in mid-level management with an upper six-figure salary for one of the smaller US oil companies (imagine a three-leaf clover as their company logo) before it was bought by one of today's up and coming energy companies. He was in his mid-forties, divorced over a year, and not seeing anyone on a regular basis. He wasn't interested in a long-term relationship having just left one, but still had business obligations to events where arm candy was almost mandatory. He also enjoyed attending the theater, as well as the symphony, but also had a fondness for indie-type music. To say I found him to be interestingly complicated would be an understatement. I also found him to be very intelligent, and could imagine him in a top management position one day if someone above him retired and/or died.

In his early forties, Steve was around six-one, and was a solid one hundred - ninety pounds with dark brown hair, and a tinge of gray at the temples. I knew he worked out despite the suit he was wearing when we first got together, and was even more impressed with his chest and abdomen when I finally say him shirtless. And damn, the man had stamina and staying power! It's almost as if he could cum on demand, which I'll get into later.

At the end of our first date, I couldn't wait until the second! Steve was the perfect gentleman who displayed manners in such an unforced way you just knew this was his everyday behavior. We each honestly told the other why we were there. I wanted my master's degree and learn from successful people along the way, he wanted a friend for social events, with benefits. I asked why a successful man needed to pay to have a woman on his arm, and in his bed, and he said even if he was still with his ex-wife, he would be paying for her company and sex. I totally got it.

Of course, my next question was why the ex? What happened? His reply was simply, "She ceased being a friend." Discussions were always about how badly her day went, how her friends seemed to have so much more fun, etc.,. Communication with her was a one-way street. Her attitude was affecting his job performance and career possibilities, and her mini eruptions at public events were embarrassing to him and the company he represented. So, as amicably as possible they divorced. He didn't want to reenter the dating scene and go through all the courtship motions again, so he opted to go where both parties knew what they wanted, seeking an arrangement where each ended up happy.

As dinner concluded he asked if I was available Saturday evening to attend a political fundraiser. I tried my best to hide my enthusiasm by asking what his job had to do with politics.

"In Texas, oil is political," Steve replied. "You could say oil money is the lubricant in the political machine."

I nodded and then asked what I should wear.

"In addition to to the $200.00 in the envelope is an extra $500.00. My executive assistant will call you in the morning to discuss what type of dress you should purchase. This is a formal event."

"You're having your secretary call me about a dress?"

"She's my executive assistant, and she has a secretary. She can advise you on what you'll need to wear. Please use her resources, Ashley has your best interests in mind, and by extension, mine as well."

"Certainly," I replied with an authentic smile. "But what if I'd decided we wouldn't see each other after tonight, what would you have done about the extra $500?"

"You're a smart and lovely young woman, and tonight was more fun than I've had in a while. While I would never imply you're predictable, I think I learned enough about you through our communications prior to tonight that if we would just be ourselves, we'd get together again."

"Saturday sounds like it'll be fun, where do I need to be and at what time?"

"Ashley will give you the details, and a car will pick you up."

"Then I should probably give you my address," I replied.

"I know where you live," Steve said as I welcomed him stepping closer into what I would normally consider my personal space. "I wouldn't be doing my due diligence if I didn't, I hope that doesn't offend you."

"Oh no, not at all. It suggests an attention to detail, foretelling a thoroughness in other areas as well," I said with a wide smile.

"Good night Leigh," Steve said laughingly before kissing me on the cheek. "It is Leigh, isn't it," he asked, smiling.

Reaching up, I placed a five second kiss on his lips before saying, "Good night Steve. And yes, Leigh is one name. But you knew that, correct?"

With that, I literally turned on my heels and walked towards my car, thinking 'damn, he smelled good!' As I mentioned earlier, once I was home and in bed I had one of my better self-pleasure episodes thinking about all the ways I wanted to use his body, and how he might use mine. Mmmm...

Ashley called at 10 am the next morning, a pleasant conversation where she recommended a flattering dress style and color for the event, and a couple of stores that would be very helpful. The last thing she said to me before the call was concluded was to be sure to bring an overnight bag when the car arrived at 6:30 pm Saturday evening. A year or two ago I would have been embarrassed at such a suggestion, but I sincerely thanked her for the kind reminder.

I ended up purchasing a very nice cream-colored corset-style formal, with a light blue waist band, which seemed to match my eyes. With one hundred eighty dollars left over I made an appointment with my stylist and hair magician Rachel to have my hair done Saturday late morning. Once in the seat she insisted I wear my hair up and expose my neck. She said my slender neck and shoulders would set off the dress, and people would certainly notice me. Later that afternoon, after I'd dressed, I was quite happy with my appearance and thought Steve would be pleased.

At exactly six-thirty there was a light knock on their door. Opening it I saw a handsome young man who introduced himself as Sean, saying he was our transportation for the evening. I introduced myself as well, reached for my leather travel bag I'd prepared earlier and had set by the door.

Sean immediately picked it up before I could, saying, "I'll make sure this is delivered to it's proper location."

I assumed he meant where Steve and I would be spending the night together. I thanked him as he held the car door open for me, and we started off for downtown. Arriving at the Belo Mansion promptly at 7 pm, I noticed four men standing out front in tuxedos seemingly engaged in conversation. I immediately recognized Steve, who turned to the car as it stopped, opened the door and reached for my hand.

Smiling to me as I emerged from the vehicle he said, "Good evening Miss Collins, you look so beautifully elegant."

I smiled as my mind immediately flashed back to my college English professor, who may have had a problem with the whole adverb-adjective combination, but I felt myself blushing nonetheless.

"Thank you, sir. My only hope is I don't embarrass such a handsome and well-dressed gentleman."

"You'll be more than fine, no doubt the envy of the other ladies when they see you in that dress. And the men will adore you. You look absolutely magnificent and glowing," he replied.

He also received a couple of comments from his friends as we started to walk in to the event, one of which was wearing a bolo tie with his tux. I was almost surprised he wasn't wearing jeans, as I looked back towards him to confirm he wasn't. This is Texas after all.

Soon we were inside, arm in arm as we moved through the crowd, a virtual who's who in Texas business and politics, stopping as we encountered the next small group of people as Steve introduced me and said hello to those he knew from his business dealings.

Less than an hour into the event Steve leaned over and spoke. "I have a little business to tend to with some clients and the Senator we'd met earlier," he whispered into my ear, "but first I'll introduce you to your guide through the tiger's den. She'll take care of you for the next thirty minutes or so."

I nodded as we approached another group of couples which included bolo tie-guy, and his date for the evening. Honestly, she looked like she would be dancing at a club down on the strip later that evening, where her double-D boobs would be rubbing on multiple customers' faces. I had to concentrate to ensure my smile didn't break out into a laugh every time I looked in both their directions - his and hers, not her boobs.

"Leigh, this is Ashley and her husband Christopher," Steve said as he introduced us.

"Chris," Christopher said as he gently took my hand in his. "No need to be any more formal than we have to," he joked.

"Hello Leigh," Ashley spoke as I turned more towards her, "It's a pleasure to meet you," she said with what appeared to be a sincere smile.

She was a beautiful woman, and could easily pass as a Hollywood stand-in for Jessica Chastain.

"And you as well," I said to her. "Also, thank you so much for all the advice. It was very helpful, not to mention a time saver."

"Yes, Cynthia certainly knows her fashion and what works well with each client. I must say," Ashley continued, "her work was easy in your case. You're positively stunning in that dress. It really compliments your skin tone and eyes."

Again, I could feel myself blushing and started to thank Ashley, but was interrupted by boob - girl.

"Hi," she practically yelled, "I'm Missy."

"Of course," I replied sarcastically, safe in knowing she'd never detect it. Ashley put the back of her closed hand to her lips trying not to laugh, as Chris simply turned his head up to the ceiling as I saw him grip his wife more firmly.

One of the servers came by and we each took a champagne flute from him.

"And who was the lucky man who accompanied you this evening," I asked as I looked directly at bolo tie-guy, taking a sip from the glass.

"Simpson Hornquist, ma'am. Pleased to meet you," he said as I almost spit my champagne at him upon hearing him pronounce his name. "And how do you know Steve?"

What a nosey-assed trouble maker I thought before replying, "He's my daddy."

This time it was Ashley who turned away, again subduing a smile and a laugh, no doubt.

"Really," replied bolo tie-guy, "I never knew Steve had a daughter your age."

"Oh, no. My father lives in Austin. I just call Steve daddy."

"Honey," Chris said to Ashley as he looked in all directions, "I thought I saw Rick and Gail over there."

"They'll be okay, I want to learn more about Leigh," Ashley told Chris. "She's an important part of Steve's life, as you know."

I knew Ashley was enjoying the word games as she winked at me. Of course, everything was going right over the head of boob-girl, but that wasn't going to stop her from staying engaged.

"So, Leigh is it? (I rolled my eyes) What do you do for fun when not at one of these affairs?" Missy asked.

I couldn't help smiling at her indelicate choice of words.

"I mean," she continued, "what exciting thing has happened to you in the last month or so?"

I could see she was trying her best to be part of the crowd, and I almost started to feel sympathy for her. Almost.

"Well, let's see. Hmmm, oh. Two weeks ago I had a tint job," I stated matter of factly before taking another sip of champagne and peering over the glass.

A collective gasp could be heard from each in the group, and I thought Chris would have a heart attack while Missy simply brought a hand up to her cleavage, mouth partially open in shock.

"My car," I then said. "I had the windows tinted while I went shopping. Lord knows, I do love to shop."

"You had your car windows tinted?" bolo tie-guy asked. "That was your excitement?"

"Oh yeah, the sun can be brutal here, as I'm sure you know," I answered. "But it was the shopping that was exciting, you know how us girls can be."

I think Chris was hyperventilating just as Steve returned. "Everyone doing okay?"

"We're all doing fine, right honey," Ashley said, turning to Chris.

"Absolutely," he replied. "Leigh has kept us all entertained. She's a charming young lady," he said trying not to laugh.

"Yes, yes she is," Steve said as he turned and lightly kissed the top of my head, as I just smiled at Ashley.