Sugar Baby

In the morning I woke to Annie blowing on my face, "What the heck?" I pushed her face away.

"You have mail." Annie used a robot voice before busting into a belly laugh. "Wake up lover girl, you have some friends."

Sitting up in the bed I pulled the computer on to my lap. I clicked the envelope in the corner at Annie's instruction. Her face was inches from mine as the screen loaded the three email responses.

The first email was from a 47 year old man. He was a nice looking man with dark hair that had some hints of greying and vibrant blue eyes. Annie and I looked at each other, "He's cute."

I smiled, "He's got grey hair!" I rolled my eyes.

"He's got salt and pepper hair." Annie corrected me.

His profile indicated that he was an established professional who was looking for someone to share fun times with while he's in town. His interests included romantic dinners, dancing, movies and spoiling his special friend.

I raised my eyebrow at Annie after reading the last part.

"Open the next one!" Annie leaned over dragging the mouse to the next email and clicked.

When the picture appeared my jaw dropped. When I looked at Annie she was smiling like on the verge of laughter, "Now that is old!"

The man in the picture was had very little hair at all and what he had was silver; liver spots dotted his balding head and skin hung from his neck. His profile indicated he was 68 years old, retired, widowed and looking for a companion to spoil. He enjoyed travel and was looking for someone to share his adventures with him.

I opened the last email.

This man had a receding blonde hairline and wore an expensive looking suit. His profile indicated that he had too much money and not enough time for a relationship. I couldn't help but give him points for his honesty as I read that he was looking for a sexually adventurous woman.

Sitting back on the bed I closed the laptop, "That was fun."

"What? Aren't you going to email that 1st one at least?" Annie nudged me.

"I don't know yet." I shrugged.

Annie mimicked my shrug, "Whatev!" then she busted in to a laugh. "Suit yourself."

The next day I logged in and re-read the first email.

Hi Lynn4U,

My name is Tim. I couldn't help but send you message when I saw your profile picture. I'm a fool for a petite green eyed redhead. Hoping you are interested in getting to know each other and seeing if we are a fit.

Tim.

When I finally decided to respond I told myself that nothing was going to happen that I didn't want to happen; I'm in control!

Hi Tim,

Thank you for replying. I'm new to this, so I don't really know how it all works or what to expect. I signed up out of curiosity mostly and am flattered by his response. You are a very handsome man.

What happens next?

Lynn.

When I got home from work I completed the ritual of dinner by slicing and poking the microwavable meal before setting the prescribed time. I couldn't resist, so I grabbed my laptop and logged in. I surprised myself with the excitement I felt seeing a new email. As I waited for the page to load I held my breath hoping it was Tim and not a new guy.

My excitement grew when I saw Tim's handle: Airman1260.

Lynn,

I am so glad you replied. I fully understand not knowing what to expect on a site like this. Hopefully I can help clarify (although I'm no expert). We meet for a coffee or meal like any other date. If we hit it off, we see each other again. We will talk about our dreams, hopes and needs and I will offer to assist you with yours if and where I can. If we don't hit it off, I've made a new friend and we go our separate ways.

What do you think?

Tim

P.S. Feel free to text or call if you prefer.

His email reaffirmed that I was in control and I had nothing to lose by meeting him. I called Annie and told her I replied; she sounded like she would explode with excitement.

"Lynn!! You have to call him!" Annie demanded.

I laughed, "Easy killer. I was going to."

We both laughed.

An awkward call turned pleasant quickly. Tim put me at ease with his smooth deep voice. He told me he lived in Texas which surprised me. He flew planes for United Airlines and was in Toronto two or three times a month. When I asked why not find someone closer, he casually explained that he wasn't looking for a wife. He has a busy career and not looking to settle down.

"I will be in town Wednesday." Tim explained, "We could go for a nice dinner if you're free?"

I began to get nervous, "Sure, it sounds fun." I proceeded to give him my cell number so he could stay in touch as we planned our first date.

It was Tuesday and I was surprised that I hadn't seen or heard from Desmond since our date. It was later in the day that usual but Desmond rolled in with his co-workers. I began making his coffee as he walked in.

When Desmond made his way to the counter he smiled knowingly at me, "How are you today beautiful?"

"I'm great. You?" I slid his coffee to him.

"Plans this weekend?" His question was transparently obvious.

I flashed a devilish smile, "Not sure yet. Ask me when it gets closer."

I spent the rest of my shift re-playing the pleasure he gave me in his truck. The intense orgasm had released the monster and found myself perpetually horny. I played with my pussy on both Sunday and Monday fantasizing that Desmond was my sugar daddy. For some reason my mind couldn't comprehend a relationship with a 47 year old man.

It was time to meet Tim. He had texted this morning confirming the address of the Keg restaurant we would be meeting at. After a long hot shower I began to prepare for my date. One of my preparations was calling Annie to calm my nerves and help me make decisions about what to wear. Happy with the gentle curls in my hair I looked myself over in the mirror one last time. My dark blue evening dress fit me well giving me that classy but not slutty look that Annie implied was the look I wanted.

I called Annie from the taxi, "I'm so freaking nervous."

"Just have fun." Annie was so cheery. "If you don't hit it off, you got a nice meal right?"

I agreed with her logic and was about to hang up the phone when she spoke again, "Don't have sex with him tonight! Not even a blowjob. You need to make him wait."

I hung up the phone as the taxi pulled in to the restaurant.

Tim made his way to the taxi quickly when he saw me climbing out, "Lynn!" He hugged me. "I'm so glad you are here. You look stunning."

After the formalities we made our way in to the dimly lit restaurant and sat at a table for two in a quiet corner.

Tim took the liberty of ordering an expensive bottle of red wine. My nerves calmed as we talked about ourselves. My concerns about people staring or his age were unwarranted. His demeanor was relaxed and inviting. I watched as his blue eyes sparkled when he explained his love of flying from a young age.

Dinner was delicious and I had no room for dessert. We sat sipping coffee as our dinner date came to a close. We talked like old friends and I knew that I would happily go out with him again if he wanted.

"Lynn, this was really nice." He smiled showing immaculate teeth. "You are even more beautiful in person."

"Thank you." I blushed. "I had a really good time."

Tim motioned for the waiter and asked him to call a taxi; it took about 15 minutes and the waiter returned to let us know it had arrived. He opened the front passenger door and handed the driver some money, "That should cover getting this beautiful little lady home."

I stood there as he opened the rear door of the taxi, "I hope I can see you again Lynn?"

"I would really like that." I gave him a hug.

Tim pulled an envelope from his jacket and handed it to me, "This is for you."

"Thank you Tim."

On the ride home I opened the envelope and counted two hundred dollars in twenties. My mind raced and challenged the morality of the situation. At home I called Annie and gave her all the details before texting Tim to thank him again for the great night.

Sitting alone on my couch I found myself wondering if Tim's age brought sexual experience that I could not conceive. I felt the warm glow of sexual sensation building and realized I had unconsciously been touching myself. My hand was not going to give me what I needed.

I looked at my phone contemplating calling Tim but Annie's words rang in my ear. I was supposed to be hard to get to lure him in for a longer term relationship. My mind then went to Desmond.

"Hey Des, it's Lynn." I tried to act casual.

Desmond immediately asked, "Do you need some company baby?" He clearly saw right through my casual call.

"Yes," my voice softened

Desmond never lost his casual voice, "Cool, I'll be there shortly."

I spent the thirty minutes playing with my pussy. My panties were off but I was still wearing my blue dress. The knock on my door was startling and I pulled my dress down as I stood. When I opened the door Desmond stood holding a box, "Someone order pizza?"

I laughed and pulled him in the door closing it behind him, "Go have a seat on the couch."

Grabbing a couple plates and headed back in to the living room placing them on the coffee table.

Desmond was sitting back on the couch smiling. I stepped between in front of him and pulled my dress up over my head, "I have something else that needs eating." As he pulled me closer with a hand on each ass cheek, I removed my bra.

"Mmm, this is gonna be way better than pizza." Desmond lifted my left leg and pressed his face between my legs putting his tongue against my bean.

I grasped his hair in my hands, "Mmm, eat my little pussy."

"Kneel on the couch!" His voice was excitingly dominant.

Desmond pushed me over the back of the couch exposing my pussy to him, "This is much better." He pressed his face deep in to me as he probed my pre-soaked pussy with his tongue.

"I don't think this pussy needs eating baby. It needs to get fucked." I watched over my shoulder as he ripped a condom wrapper open.

Seconds later his hard cock was toying at my opening, I pushed my hips back eagerly awaiting him to penetrate me. Desmond slowly worked his cock in to me until he was fully in me; holding himself still he squeezed my breasts and began to slowly work himself in and out of me.

As his thrusts began harder and faster his hands moved to my hips. I gasped out each time he buried himself in me. My pussy loved every minute of it, especially when his balls slapped against my clit.

It felt amazing but I couldn't cum so I pushed him down on the couch and straddled him. Lowering myself slowly on his cock I sat up tall and ground myself off his pubic bone. The feeling of a building orgasm told me this was what I needed. Our eyes locked on each other as I continued my slow grind.

Desmond squeezed my breasts firmly, "Yeah baby! Ride my fucking cock."

I sucked my bottom lip between my teeth as my orgasm neared, "I'm gonna cum."

"Yeah baby, cum all over that cock." He released one of my breasts and grabbed a handful of hair pulling my lips to his.

I sucked Desmond's tongue in to my mouth working it like a cock. Desmond began thrusting in to me and panting in my mouth, "cum with me baby." We were both panting and grinding wildly as our bodies worked out the perfect rhythm.

"I'm cumming." My body convulsed as wave over wave washed over me.

Desmond thrusted up wildly as his cock exploded, "Oh fuck baby, milk that fucking cock."

I rode him wildly until his thrusting stopped. Keeping his cock in me I kissed him as he played with my breasts, "How was that?"

"That was fucking amazing!" He squeezed my breasts tugging on my nipples.

We sat naked on the couch eating pizza and drinking Pepsi's for an hour before Desmond had to head out. We kissed and I was alone with my sated pussy.

I awoke to the chime of a text message from Tim.

Tim:I really enjoyed our time. I will be back in a week; I would love to see you again.

Lynn:I can't wait to see you.

Tim:Great, we will talk soon.