College Fund Ch. 05

After dinner, while sipping Creme de Menthe, I placed my hand on his thigh and gently massaged him. I could feel his bulge on the back of my hand. I wondered how long he'd had an erection.

While taking the last gulp of my drink, I boldly grasped his hard cock and squeezed - he nearly leapt off the seat.

"Would you like to go out to my car?" I softly asked him.

He was tongue-tied at first (how cute!), but then said, "I have a room at the motel across the street...would you, uh, like to go there?"

"Why you naughty boy! You ply me with food and liquor so you can have your way with me in a motel room?" I said playfully.

His face turned beet-red as he stammered for words.

"Oh, no, no...it's only, uh, well, my place is being painted and I'm allergic to the fumes...I have the motel room through this coming Friday...I was just wondering if, uh-"

"I would love to see your motel room, Mister" I interrupted his embarrassment with a smile.

I didn't challenge him when the server brought the check. I want him to be the assertive one in our relationship, and promised myself I'd try hard not to do or say anything that may emasculate him.

Outside the restaurant, standing at the corner waiting for the light to turn 'green,' he pleasantly surprised me by taking my hand in his.

We were half-way across the street when a car made a left-turn out of the restaurant parking lot coming close to hitting us.

"GET A ROOM, YOU FAGGOTS!" shouted someone inside the car.

"We already have one," Andy said softly to no one in particular.

I was so pleased to hear him say that I held onto his hand tighter.

I had never paid much attention to the motel, but as we walked to his room I was impressed.

Oh my goodness, I thought, this place is so nice he's got to be paying over two-hundred a night! How can he afford it?

He stopped before a door and ran a card key over the scanner and the lock popped open. I was suddenly consumed with fear. How in the world was I going to explain my new breasts to him?

When I entered the room, I was momentarily confused - I saw a long sofa, but no bed. There was a kitchen off to my right, and further in I saw a door I assumed led to a separate bedroom.

Oh my goodness - this is a suite! Once again I asked myself, how can he afford this?

"Would you like a glass of wine?" he asked.

"I'd love one," I replied.

We sat side-by-side on the sofa. We sipped at the same time then Andy set down his glass, put his arm around me and drew me close, then we kissed. A nice kiss; a long kiss; his tongue pushed at my lips and I allowed it inside my mouth.

When we broke, we both gasped for air.

"Andy, there's something I have to tell you," I said softly.

He squinted at me and saw the concern on my face. He cautiously said, "Uh, okay...what is it?"

"My, uh, body has changed...I've been working on my chest the past week - it's slightly different - it's uh, a little more 'pronounced' than it was before..." I carefully said.

"What does that mean?" he asked with furrowed brows.

I looked away from him and said, "It was mentioned to me at work that my nipples were rather smallish, and men would find me more appealing if they were longer..."

I couldn't say I did it for Mister X; I had to make it sound more general than that.

"How is that even possible?" he asked.

I took a deep breath and explained the process...of bending over while five-ounce steel balls hung from my nipples stretching them...how afterwards I sat on someones lap and he tugged and pulled on my breasts and nipples.

"My God, John, that sounds painful...did it hurt much?" he asked.

I was so relieved he was concerned about the pain I went through and not the fact I had it done at all, I threw my arms around him and hugged him close.

I decided to confront my biggest fear and said to him, "I hope this doesn't change how you feel about me - I hope you don't find me disgusting," I said; then whispered in his ear, "I'd simply die if you thought I was a freak - I don't want to lose you..."

Before he had a chance to respond, I stood up and slowly unbuttoned my dress shirt. When I pulled it off I looked down and sure enough, there were prominent bulges pushing out the tee shirt.

His eyes grew wide as I pulled the tee shirt over my head and stood with my hands clasped behind my back. I couldn't decipher the expression on his face - I had to look away from him.

He sat a few more seconds then stood close to me with his hands on my shoulders.

He asked in barely a whisper, "Do they hurt?"

I said, "They did up until today."

"John, those are the sexiest things I've ever seen - may I touch them?" he asked.

I breathed a sigh of relief and felt tears well in my eyes. I found his hand and slowly raised it to my chest. His touch was soft and gentle. He caressed them for a minute then surprised me by lowering his mouth to a nipple and closing his lips around it. He flicked at it with his tongue and both nipples grew to their full length.

An animal-like groan escaped his mouth. I stroked the back of his head as he alternated taking each nipple into his mouth, gently sucking on them.

I reached down and found the bulge in his slacks and caressed it. He backed away so fast I thought I did something wrong.

With a sheepish grin on his handsome face he said, "You keep doing that and I'll cum in my pants...let's move to the bedroom, okay?"

I threw my arms around him, gave him a soft kiss on the lips and said, "I thought you would never ask."

I was standing outside the parking lot door of my apartment building at 6:20pm. I'd been told Timmy would pick me up at 6:30. I am rather anal when it comes to being on time.

At 6:31, a black Mercedes S65 AMG Coupe stopped in front of me. The only reason I knew the make and model of the SUV was because Tommy, the owner of the fitness centers has one. I was told the cost of the vehicle is well over $200,000.

The drivers side window lowered but it was too dark to see a face.

"Johnny, I'm Timmy, get inside the car!" said a voice in the darkness.

The passenger-side seat was pushed all the way back which gave me more than enough leg room.

"No, sit on the floor!" said the voice.

I hesitated and 'Timmy' repeated "On the floor!"

"Yes, sir," I said to him and scrunched myself on the floor in front of the seat.

He handed me something and said, "Cover your eyes with this!"

Fumbling in the dark car, I figured out I was holding some sort of mask. I adjusted the elastic band on the back of my head then lowered the mask over my eyes.

I then felt something on my arm and heard him say, "Put these headphones over your ears!"

They were big, and when I had them in place, I briefly panicked - I couldn't see or hear anything; it is scary to suddenly lose your vision and hearing. Billy had warned me this would happen, that they didn't want me to know where Mister X lives, but it was still rather unsettling.

The SUV lurched forward and I fell back against the seat. I took deep breaths to calm my agitated nerves, but my pulse was racing hard so I allowed my mind to drift back to the night before with Andy.

His reaction to my new chest delighted me. His previous gentle and submissive demeanor literally changed over night. He became an animal in bed. He was all over me; kissing and licking my face and chest continually making small grunting noises.

When his moans grew louder, he positioned me sitting upright with my back leaning on a pillow. He wasted no time in placing his knees on either side of my shoulders, his hard prick inches from my parted lips.

He stroked my face and said, "Take it in your mouth, sweetie...suck my cock you pretty little boy!"

I sucked him slowly, casually licking at his turgid flesh...until that is, he became impatient and began to forcefully thrust his erection between my greedily clasping lips.

His only interest at this time, like every man, is to rapidly piston his hard penis in-and-out of my mouth...to relieve the unbearable pressure he was feeling in his heavy and swollen balls.

He was beyond what I call 'The Point of No Return' - when a man loses the ability to use his mind for rational thought, instead, he reverts back to his neanderthal-roots feeling only the biological necessity to empty his balls into the nearest warm orifice he can find.

When a man reaches 'The Point of No Return' - it matters not a whit if he is using a mouth - an asshole - or pussy, heck, he could be sliding his dick back-and-forth through a plate of warm spaghetti for all he cares...his singular goal is to shoot his load and relieve the intense pressure in his balls - that's it...period...end of story!

I felt myself smiling as I recalled the difficulty I had trying to gulp down stream-after-stream of his sperm and semen. I was already aware of the enormous quantity of fluids his balls could store, but it took a Herculean-effort on my part to not allow a single drop from escaping my mouth.

The SUV abruptly stopped and I wondered if we had arrived to wherever-it-was we were going. I waited then suddenly the car jumped forward again; it had only been a red light. , I guessed.

Timmy's driving skills left much to be desired. His jackrabbit starts and sudden stops were making me dizzy.

I again drifted back in time and remembered the mind-numbing climax Andy finally gave me after I'd sucked him off the second time. His hands are as gifted as an artist, or a concert pianist.

He has the ability to know how to lower my balls and prevent my orgasm at just the right time. When he finally allowed me to climax, it was only because of my pleading and begging. No man has ever gotten me as excited as Andy had last night.

The car came to another prolonged stop and I waited. A rush of cool air came from my right-side and I knew Timmy had opened the car door. He gently removed the headphones and mask.

"Okay, we're here, cutie," he said.

I was relieved to hear his sing-song voice call me 'Cutie.' Billy had told me how Timmy at one time, when he was much younger, was Mister X's butt-boy, and once he became older Mister X no longer desired him. I was afraid Timmy would be jealous of me, and treat me badly.

He helped me out of the car, and when my eyes could focus I was staring at a ranch-style house.

I commented, "It's smaller than I thought it would be..."

Timmy chuckled and simply said, "This is the guest house."

I followed him inside the house. I wasn't nervous because Billy had told me I wouldn't see Mister X until I was bathed and dressed.

Timmy led me straight to a bedroom. On the left-side was a large bathroom. Timmy immediately ran water in the tub, and sprinkled what I guessed was bubble bath soap.

"Take off your clothes, cutie," he said with a wink of an eye.

"Yes, sir," I replied and began stripping.

Working at the fitness center prepared me to be naked in front of strangers. Besides that, I am proud of my body and enjoy showing it off.

"Ooo, what cute little titties," he exclaimed when he saw my chest. "Billy did a wonderful job with you!"

I cursed myself for blushing.

"You're still a virgin, cutie, correct?" he asked.

"Yes, sir," I replied.

"Did Billy train your pussy with the dildos?" he asked. And when he saw me wince from the delicate nature of his question, he smiled and added, "There will be no secrets between you and me, cutie...you and I are going to get to know each other v-e-r-y intimately!"

"Oh," I exclaimed and blushed one more time.

I watched him remove a rubber bag from beneath the bathroom sink, and recognized it immediately.

He ran the hot water and poured some liquid soap into the bag then filled it with water.

He smiled at me and said, "Okay, cutie, spread your legs, bend over and reach behind you and pull apart your cheeks - it's enema time!"

I closed my eyes and did as I was told.

I couldn't believe the amount of liquid he squirted inside me. Each time he paused I thought it was over only to have him squeeze more soapy water into me.

When he finally did finish, I wanted to sit on the toilet seat immediately but he stopped me.

"I'll let you know when you can sit - keep your pussy clenched shut!" he said.

"Y-Yes, sir," I said in a shaky voice.

Easier said than done, I thought as I fought hard to obey his command...'pussy'? That's the second time he referred to my asshole as a 'pussy.'

The realization set in that Mister X would be using my 'pussy' not my asshole. Billy and I had even run through role-playing games where he himself called it my pussy.

My heart began to beat faster when I told myself 'This is no game, John, it's about to become very real!'

I had a belly-ache like never before. I couldn't take much more.

"Go ahead - sit down, cutie - let it all out of you!" said Timmy.

The moment I sat on the seat my sphincter loosened and what followed can only be described as loud, smelly and gross. Enough of that...

Timmy had gone into the bedroom while I was 'evacuating'...when he returned he was wearing nothing but a white jockstrap. He stood over me waiting...I looked at him really for the first time. I was struck by the similarities we shared.

We were the same height, and he out-weighed me only because he had a slight paunch to his stomach. His hands and feet were identical size to mine, and the small bulge in the pouch of his jock was the same as mine.

I glanced upward at him...blue eyes, pouty lips and an infectious smile - yes, he was identical to me in almost every way except for the age-lines on his face - he looked every bit over forty...but if I closed my eyes I could picture him twenty-years earlier as my twin...I suddenly felt sad for him...

He wouldn't have stayed with Mister X all these years if he wasn't in love him, would he? And now his job was to recruit and train younger guys to be his replacement. My heart went out to him...

The rumblings in my belly came to a halt. I was tired, it felt like I had expelled gallons of liquid.

"It's time for your bath - wipe yourself, cutie, then climb into the tub!" he said.

"Yes, sir," I replied, suddenly willing to do whatever he wanted from me.

I understood why he had stripped to his jock. He knelt at the side of the tub and literally bathed me himself. He had me sit back as he washed every square inch of my body. When he was finished, I was totally calm and relaxed. He even dried me with a richly, thick towel.

"Okay, cutie, bend over for me one more time!" he instructed.

"Yes, sir," I said, and like before, spread my legs wide and pulled apart my buttocks for him.

I saw a long, thin tube and a tall bottle of oil. He pushed the tube into the bottle then gently inserted the oiled tube inside my asshole. He repeated this until he was satisfied I was sufficiently oiled to take Mister X's cock inside me.

I followed him into the bedroom and had to smile when I saw my 'outfit' laid out on the bed - all white...they were going to play this 'virginal' angle to the hilt!

It surprised me when he handed me the panties. They were not at all what I expected. Playing a school-girl, I figured I'd be wearing cotton panties with maybe balloons or teddy bears on them...but no, they were nylon and see-thru...very adult panties!

I slid them up my legs. Something was happening to me when the material came in contact with my flesh. My prick began moving. I ignored it and pulled them up in place.

Oh my goodness, the nylon felt sooo good on my penis and balls I sprung a rigid boner. I blushed a furious red.

Timmy chuckled and said, "Billy didn't tell me you have a panty-fetish!"

I stammered, "Well, uh, no, no, I've never had a thing for women's underwear - never thought about it until now...I'm sorry, I don't know why this is happening!"

He stood before me and boldly squeezed my hard-on through the panties. I swooned and nearly fell over.

He laughed again and said, "Well, cutie, if you didn't know it before you certainly do now - you love wearing women's panties!"

"But, no, I can't...I mean why?" I protested.

"Cutie," he said, "...there is no explaining why for the things we like - it is what it is..."

I watched in embarrassment as he walked to a chest of drawers and retrieved something from inside.

He returned to me and said, "Lower the panties to your knees!"

"Y-Yes, s-sir," I stuttered, and did as I was told.

He showed me a leather band about an inch wide, and maybe three-inches long.

I watched him wrap the strap around the top of my scrotum and then tighten it until I squeaked "Ouch."

He fastened it in place and stood back to admire his handy-work.

"The worst thing you could do would be to climax before he wants you to...this will prevent any 'accidents'!" he said.

"W-What do you mean?" I asked.

"Haven't you heard of men who like to deny their boy's orgasm by 'cinching their balls'?" he asked me.

"No, uh..." I mumbled.

"You do know when you ejaculate your balls rise to the top of your scrotum, right?" he said.

"Uh, I guess so," I answered.

"Well, this seemingly harmless little strap will prevent you from cumming...your balls will not be able to rise - you will not be able to climax while you are wearing this," he explained.

"Ohhhhh..." I suddenly understood and sighed.

"There is a benefit to wearing this..." he said. "The longer your orgasm is denied the more excited you will become...and when you are finally permitted to cum - oh my God, you'll simply explode with the greatest orgasm of your life!"

"OH," I said with eyes wide open.

I glanced down to see my hairless balls looking grotesquely large underneath the tight strap. He tugged the panties back up into place and again squeezed my cock.

"Ohhhhh..." I gasped.

He picked up a brassiere and said, "Raise your arms, I'll show you how to do this..."

It too was an adult garment and a rather flimsy one at that. It was silky with a lace pattern on the sides of the cups.

When he had it in place he said, "Reach behind and see if you can fasten it yourself!"

I heard soft laughter as my hands struggled to fasten it. It took six or seven tries before I could accomplish that simple feat.

My prick twitched when my nipples pressed against the soft material. It was a very tight fit, and my nipples blossomed to their full length.

"Ooooo, perfect size!" he said, then added, "Don't worry, you'll become an expert fastening it in a short time."

He slipped a white blouse over my shoulders. When I tried to button it he saw my confusion and laughed again.

"Yes, the buttons are on the 'wrong side' aren't they?" he said.

My face reddened as, and with some difficulty, finally managed to button it.

He handed me the white, pleated skirt and I looked for the label, not wanting to put it on backwards and have him laugh at me again. Oh my goodness, the skirt hung only to mid-thigh.

I sat on the bed as I pulled on the white anklets then he pointed at the white, patent leather shoes on the floor. They were small, but I was grateful they weren't high-heels.

It stunned me when I saw him walking towards me carrying a wig of blonde, curly hair.

Oh my goodness, Mister X thought of everything. When Timmy adjusted it in place, he helped me to a floor length wall mirror. My heart stopped briefly when I saw my reflection.

My eyes moved up and down, not quite believing what they were seeing in the mirror.

What I saw was a pretty girl with creamy, alabaster legs, young breasts straining against the white blouse, and a head full of short, girly curls. I fully understood now the depravity of what was about to take place.

Timmy said, "Stay here!" and left me standing in the bedroom.

He returned almost immediately and announced, "It's showtime - your 'Daddy' is waiting for you in the living room!"