The Sugar Daddy

Why does wanting to be a cuckold such a bad thing? I've written about it and posted such stories on Literotica only to be told I'm a moron and pile of dog shit. What are people so afraid of that they can't handle themselves cordially when one man wants to explore an open-marriage where primarily the wife is pleasured by another man? I don't get it and probably never will.

My first wife didn't get it either. No matter how hard I tried to persuade her she wouldn't give in to my fantasy. So, I divorced her about five years ago. She's happily married to a retired professional athlete and they have a couple kids. They look like the poster marriage of an all-American family. I'm glad for her.

That divorce cost me a bundle though. I lost 25% of my family inheritance in cash and stocks as well as our house. We were 35 and 33 at the time. I'm 40 now so you do the math. Yes, moron she was younger.

I am married now to a 50-year old Dominant Latina. She is unusually beautiful for her age and standing only 5'2" to my 6'4" we look ridiculous together. More so when I am collared, leashed and on my hands and knees. When I'm kneeling upright and she's standing, we can see eye to eye. Besides the physical and racial differences, we have so much in common its funny.

We met through paid phone sex. She had a sexy ad featuring a teen age Latina skilled at manipulating older men for their money. The first time I called her she was just waking up and I just wanted to introduce myself and then call back later when I had more time. Also, I had about $10 in my account balance and thought that to be sufficient for making an assessment of her skill.

My plan was out the window along with my good judgment the moment I heard her voice. She spoke with confidence bordering on arrogance and sent me several pictures of herself by the pool. After the $10 was used up, she suggested that I refresh my account with $150 so we could get to know each other better. I liked her suggestion and off we went.

We talked almost daily after that and to those in the phone sex domination business I was referred to as a rainbow with the pot of gold. We had a lot of fun. Each day there was a different topic to discuss and then we got into the phone sex and masturbation part. She often played along with me so between us there were several orgasms per call. Her business angle was to keep me on the phone and so she told me the one thing I wanted to know anyway was the more money I gave her the wetter she got.

One day she told me she went shopping and bought lingerie, hair and nail salon treatments and a Brazilian using all the money I had given her. Then she paused while I felt my dick harden. "Baby, I over did it and I need more to pay my bills" she said and then my inbox received a payment request email. "Rub your cock for me Bob" she said "and click that pay button for me when you're ready." Again she paused as I stroked my dick. The pleasure intensity was climbing and made me more than ready to click. And even when I saw the amount and knew it was too much, I clicked it anyway and said "I can't help it I think I love you."

"I know you do Bob and I appreciate your honesty. I love you too and I'm going to keep taking from you until you have nothing left to give. Now stroke your cock and make it cum. I have things to do."

I know it sounds harsh as you read this but if you could have heard the softness in her voice you would be closer to understanding why I gave her so much money. It was my method of surrender and her method of domination and it worked for us for a long time. After my divorce was final, I called my phone sex Mistress to tell her the good news. I had kept it from her primarily because our sessions were an escape from all the bad shit my wife and her lawyer pulled. The news took her by surprise and she asked if I did it because I wanted to meet my Mistress and serve her in person.

Her question surprised me and I said "Not exactly, but the thought has crossed my mind."

"Mine too" she responded. "I would love to meet you Bob and engage in all the fantasies we have shared."

"That would be so hot Mistress."

I stroked my hard dick. Things were going way better than expected. We were headed in a new direction and I felt free to go there with her. "It's exciting because I can call you anytime you want now. I don't have to sneak away Mistress."

"You're really serious aren't you? You divorced that cunt of a wife and you want to surrender at my feet real time."

"Yes." I didn't hate my ex-wife. I just didn't want to be with someone who was so unwilling to dominate me.

"As long as we're sharing news, I've got some for you too" she said.

"Please don't tell me you're dumping me."

"No nothing like that. I care about you Bob. I know I take from you but I think we have great chemistry and you need to know the truth about me before we go any further."

"You're married and have kids?"

"No. I'm divorced and there are no kids."

"So you're not 19 then either?" I asked half serious.

"No. I'm 48."

"Jesus, you're older than my ex wife" I said. "But your voice makes you sound so young. What do you look like then?"

"I'm still attractive" she said. "Here's an email with my picture in it."

While I waited for the email I said "What's your real name?"

"Mary" she said.

The picture made her look stunning. She had all the attributes that a man desires when he looks at her: a healthy face and smile, wavy hair and a billowing chest underneath a black stretchy tee and an open, unbuttoned white top to start. Down below that was equally impressive with: small hips, the promise of a tight butt underneath a mini skirt, shapely legs and black open toed high heels. She was a real sexy looker.

"How old are you in this picture Mary?"

"48, it was taken a few weeks ago."

"You look exceptional. Is this how you dress normally?"

"Sometimes I wear jeans and a wife beater."

My jaw dropped and my dick was rock hard and ready for action. We could both get into action with Mary. She was HOT!!!

"Do you have any other pictures of you in other outfits? Nothing nude, just everyday wear so I can get a better feel of who you might be."

"Not so fast Mister" she said playfully. "First I want to see one of you too. I want to know I'm not falling for some fat slob with ugly written all over his forehead."

I laughed hard. It never occurred to me that the opposite sex would think like I do. We were building trust in one another and it felt good to start with real pictures. "I have some on a camera that I can send you. I think my ex-wife took them so they're this year but a few months ago. Don't worry I look the same."

She laughed too. "Do you have a cam?"

"Yes, but its not hooked up and I'm not dressed either."

"Go get it. I want to inspect my property." She was moving into character, but now mixing our fantasy with reality. I wanted to stop and ask if she was playing or serious about giving me an examination and whether or not I should worry about passing. My palms felt moist and my dick softened slightly as nervousness kicked in.

"Okay. You win. I will show you what I look like on cam. Can I call you back once I have it set up?"

"No baby, I want to rape your wallet. Put the phone down and set up your cam. Then come back and stroke your cock for me while I check you out."

I setup cam in record time and sent her the instant message ID for the cam service I use.

"What does FBsucks8+ stand for?"

"Fluffer boy sucks 8 inch cocks or better."

"I like that. When you become my husband I think we'll change that to fluffer boy sucks black cock only."

Again Mary's comments struck a chord with me. If only I knew she were serious, I'd become her's in a heart beat. Regardless, my heart beat faster than ever as she acknowledged receipt of the cam invite. About the same time the status on my screen showed one viewer, I heard her gasp.

"You're really handsome" she began. "I was expecting you to be fat, but oh my..." her voice trailed off.

I moved the cam to show her the rest of my body: firm chest with good pecs, and flat stomach. I skipped over my crotch and showed her my small ass then back around to show her my muscular quads and then the back side of my legs again so she could see my calves. "You really do work out" she said with interest.

"Yes. I do."

"Can I see your cock please?" she asked.

"I have it bound right now."

"Show me" she whispered.

I moved the cam so she could see my bound cock and balls. "I like what you've done. It's home-made and shows creativity" she said. "Are those leather strips?"

"Yes. I removed them from an old pair of boat shoes. There are four strands, each approximately 18 inches in length. I have two coiled at the neck of my ball sac and wrapping downward to compress the balls into a confined space. The other two strands are coiled on the length of my shaft from crown to base. They keep it hard."

"Does it hurt?"

"The leather is firm and oiled but still invokes some discomfort."

"Can you stroke it like that?"

"Yes, but not the same way as if I were just lubed. It's more of a fist pumping and head stretching activity with slow build up. It takes a while and if I tied it right, the leather bites into my flesh as the head expands just before orgasm."

"Show me. I want to see that."

Just then the operator interrupted us with her 1 minute cutoff warning.

"Do you have a pencil?" asked Mary.

"Yes."

"Here's my personal phone number" she began and then told me the digits. I repeated the numbers back to her as my heart fluttered. This was a definite 'no-no' in the phone sex biz, but I felt complimented just the same. Just because she gave it to me didn't mean I had to call her with it. I could still protect my identity by not calling on my cell phone.

The operator came on again and requested more money to continue the call. That was way to fast for a minute and I made a mental note to watch the clock next time. While the operator recited my options I looked at the number Mary had given me, hung up the phone and dialed her number instead.

After four rings, she answered "Hello"

"Hi, this is Bob."

"Hi."

"Why did you give me your phone number?"

"I like you and I want to get to know you better" she said.

"I never anticipated that. Thank you Mary. How often can I call you?"

"Call me anytime. Leave a message if I don't answer."

"I get horny a lot you may regret this."

"I expect to be pampered too Bob. That will never change. This is not a free sex number. I put some faith in you by trusting you with it. Now it's your turn to reciprocate. Impress me with $3000 by pay pal."

"What?"

"Do you have an account there?"

"Yes"

"Then you know how it works. Log in and enter my email address. Then make me wet my panties for you."

"That's too much Mary. I won't do that."

"Yes you will. You will do it now and every month you will send another of the same amount. It's my allowance from my sugar daddy."

"But you're older than me."

A web cam invite popped onto my screen. The user ID was Mary's and I clicked accept. A view of her sitting at her computer desk filled my screen and I could clearly see her looking at me and smiling. She was fully dressed in a red sweater. Her eyes sparkled and her carmel skin was beautiful even on web cam. I knew we were real now and we were going to cross the chasm in a spectacular way.

"I'm older and wiser than you'll find out there in the real world. I'm also attractive and open-minded enough to take care of all your fantasies as long as you take care of me" she said.

"I'll give you $1000" I said.

"This is not a negotiation Bob. The base is $3000 a month plus all expenses for travel and clothes, dining etc. when we're together."

"You're serious."

"Yes. Now throw in another thou just to say you're sorry for hurting my feelings."

I looked down at my dick and we communicated telepathically. He said 'pay her dumbshit!' and I said 'you better be right!'

Then I looked at the web cam and said "okay."

"Point the cam at your screen and show me you're going in. I want to watch."

"You'll see my last name and where I live."

"I know. Show me. I think you want to. It's a rush to reveal yourself to me isn't it?"

"Yes" I said and nodded at the back of the camera. I had already pointed it to my screen and then I found my bookmark for pay pal and clicked on it. Fortunately my keyboard was behind the cam. I didn't need for her to know my password.

Mary put her feet on her desk and her calf suddenly blocked my view of her. "Your leg just covered up my view." I said "Will you move the cam so I can see what you're doing?"

"I'm going to masturbate" she said. "It's been a long time since I had a sugar daddy. It's a celebration for me darling."

"You've done this before?" I asked and paused at the confirmation prompt.

"Don't get jealous on me darling. I do what I have to and now you're going to do what you have to. You do want me don't you? Look at my leg and think about licking all the way up to my creamy pussy."

"Jesus. You're going to kill me."

"Yes baby. I'm going to give you so much sex you will die of a heart attack."

"That's all I ever wanted."

"I know" she whispered. Her leg remained where it was, blocking my view but looking sexy none the less. It was definitely a leg I wanted to feel on the side of my face and so without further delay I turned my focus to the pay pal screen and looked at the input fields. Her email address was correct and there below it in the dollar field was 4000. If I was going to be a sugar daddy, then five grand suddenly seemed much more impressive. So I changed the number, whispered 'here goes nothing' and then clicked send.

The screen refreshed with a message confirming the payment was sent.

"Wow. Baby you have been so good to me" she said in the sweetest tone imaginable. "Now I want you to stroke that cock for me while I accept your funds into my account."

I stroked and asked "do you want to watch my cock erupt on cam for you?"

"Absolutely darling."

After I moved the camera to face me again she said "I think you deserve to take the leather strips off don't you baby?"

"Thank you Mistress."

"You're welcome" she said.