College Fund Ch. 05

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Ass

“Ohhh, yesss…that is sooo nice…your hands are sooo magical,” I heard Terry the Towel Boy say to someone.

I craned my neck to peer between two bodies and saw Willie Mumphrey, an aide to Congressman Hecker, showing one of his drawings to Terry.

The Congressman himself immediately joked, “Yes, and his hands sketch very well, too!”

I had seen those drawings myself. He specialized in sketching hugely grotesque cocks with impossibly massive balls hanging below. I thought them more disturbing than erotic.

I went about my business of replacing used, wet towels with clean, dry ones. I found myself humming a favorite song and smiled. The previous evenings dinner with Andy had given me a warm after-glow in which I was still basking.

Dinner with Andy was like being with a friend I had known forever. Our conversation was never forced; our words flowed freely, and I was relieved to find him less shy, and more outgoing than our previous encounters at the gym.

Perhaps the two orgasms I’d given him earlier that day had something to do with it, ha-ha-ha…

After we had our Tortellini soup, and waited for the Veal Scallopini to arrive, Andy rested his arms on the table as he spoke.

“You know, John, I envy you,” he said wistfully.

I placed my hands on top of his to see his reaction, then softly laughed and said, “Envy me? Why would you envy me?”

He remained calm. He didn’t pull his hands from mine, or look nervously around the room to see if people were watching us. His acceptance of this small show of public affection thrilled me.

“You seem so comfortable being who you are – even happy,” he said.

I saw a troubled look in his eyes and instinctively knew he was consumed with conflicting emotions bubbling beneath the surface of his heart and mind…he is me – at least the way I used to be before I came out of the closet.

He continued: “Obviously I must be gay…but it’s something I haven’t been able to understand…I think I work long hours so I won’t have much personal time to deal with it…how do you do it? Is there some secret I don’t know about?”

I squeezed his hands then pulled mine away. There was no point in belaboring the affection and make him feel embarrassed.

“Andy, it wasn’t too long ago I felt the same as you…you grow up thinking these strange feelings you have is just a passing phase…that some day you’ll meet the woman of your dreams – marry – settle down and have kids like normal people…you date women you’re not attracted to just so your friends and family won’t think there’s something wrong with you…”

He nodded solemnly. “I know…there were two girls in my past I went with for a couple years each…I had to force myself to make love to them…for awhile I fooled myself into believing I enjoyed it, but it didn’t take long to lose interest…in the end, I am sure both girls knew I was gay before I did.”

“And you weren’t very happy, were you?” I asked.

“No…I was just going thru the motions…like you said, I was doing what was expected of me,” he replied.

“Andy, I really don’t know how other gay guys deal with their situations. I think it’s different for everybody…in my case, I was so embarrassed of my feelings for men I had to move away from the city I grew up in so my friends and family wouldn’t find out I’m queer.”

“Do they know it now?” he asked.

“Yes, they do…the funny thing is, as it turned out, most of them did think I was gay but never said anything – they didn’t care…sometimes our own minds create problems that aren’t there.”

Andy flashed me a wide grin and said, “You know, John, sometimes you sound so wise that it’s hard to believe I’m twelve-years older than you.”

I smiled and said, “You are only as old as you feel in your heart…anyway, I love hot, old guys like you…”

We were both quietly smiling and laughing when our meals arrived.

Dinner was scrumptious! We ordered two Amaretto’s afterwards and sipped our drinks as we casually chatted.

We had been sitting directly across from one another, but I moved my chair next to his so I wouldn’t have to talk so loud.

“Andy, there is something I need to speak to you about,” I said.

“Oooo, it sounds serious,” he replied.

I leaned over, placed a hand on his upper leg, and said, “It is serious…”

He furrowed his brow and said, “What is it? I hope you know you can talk to me about anything – I am here for you, John.”

Oh my goodness – his answer and concern warmed my heart – I felt so close to him I knew I could say anything to him.

“There is a rule at work that forbids us from dating our clients…” I said.

“We’re only having dinner…” he said.

“I know, but if my boss finds out I was here with you he could fire me,” I explained.

“I certainly won’t tell him we shared our meat with each other,” he said with a smile trying to lighten the mood.

When I gave him a slight frown he added: “John, I’ll quit going there if that’s what it takes – I can always casino siteleri find another gym.”

It was the answer I was hoping for. “Andy, I like you – I like you a lot…it’s just that, well, I’m wondering what you want out of this…I know you don’t have much experience with, uh, being gay, and I can’t help but wonder…”

Now I became the shy one. I couldn’t look at him when I asked, “I can’t help but wonder if I’m a ‘fling’ to you…or if you think we might have something real here?”

He didn’t immediately answer and I became uncomfortable with the silence so I squeezed his leg. We stared into each others eyes. More silence…instead of removing my hand, I began to slowly rub his thigh, my hand stopping just short of his crotch.

I couldn’t take the tension I was feeling any longer so I said, “I’ve had a great time tonight…you’re fun and so easy to talk with it seems like we’re old friends…”

He suddenly broke his silence. “John, I, uh, I’m not sure how to answer your question…I like you, too – I love being with you…this is all so new to me I’ve got a million thoughts running thru my head…I do want to see more you-“

I interrupted him. “Let’s talk about this another time…it’s not fair to put pressure on you…I want to see more of you, too…let’s just keep it at that for now,” I said then lightly brushed the crotch of his dress slacks with the palm of my hand. Sure enough, he was hard as a rock.

“Maybe we can finish this conversation in the backseat of my car?” I asked with a coquettish smile and a squeeze of his erection.

His eyes glazed over. I saw beads of perspiration on his forehead.

He coughed and replied, “Uh, yeah, uh, that would be nice…”

I boldly grasped his cock below the table, squeezed it harder and said, “I’ll make it more than just ‘nice’ for you.”

The waiter brought the check and we both reached for it.

“John, please,” he said. “I told you I’d buy so let me pick up the check.”

I let him have his way and said, “Well then, I insist on giving you dessert!”

I loved the look of surprise on his rapidly reddening face.

When we walked out of the restaurant I watched him subtly try to hide the bulge in his slacks with a hand dangling before him. Truth be told, I was thrilled that I could get him so excited.

I had intentionally parked the car in the darkest part of the lot hoping this would happen.

It’s not easy to climb into the backseat of an older Toyota Corolla but we managed. We settled close together, our legs touching.

A question came to mind and I briefly wondered if I should ask it, but I felt so comfortable with him, and he with me, I went for it.

I wanted to ask him, Andy, how many guys have you been with? But decided it was too personal this early in our relationship.

I placed a hand on the back of his head, and slowly pulled him to me until our lips were touching. A gentle peck quickly turned into a passionate kiss and embrace. My own prick stiffened inside my briefs.

We were both out of breath when the kiss ended. I placed my hand on his thigh and gently stroked it. To my surprise, he did the same for me. We kissed again – deeply, more intense – our tongues danced and licked at each other.

I found the bulge in his slacks and squeezed. I nearly came in my briefs when he did the same for me. I decided to be more aggressive to prove I was the submissive one – I know, that doesn’t make much sense, but anyway, I unfastened his belt and opened his slacks…to my chagrin, he did the same for me.

Now it felt more like a contest of who is the ‘top’ and who is the ‘bottom’…it was a first for me…all the other guys correctly assumed I was the ‘bottom.’

I reached beneath the waistband of his boxers and boldly grasped his hard cock (Boxers! That’s a sign of a ‘top’ isn’t it?)…he did the exact same thing for me.

We were moaning and groaning into each others open mouths. I released my hold on him and tugged at his slacks – he lifted his hips to allow me to lower the slacks and boxers. He followed my lead by tugging at my slacks and undies and I too lifted my hips at the appropriate time.

I caressed and stroked his shaft and his balls…darn it – he immediately did the same for me.

I took his hard cock in my hand, squeezed, then asked him “Am I gripping it too tightly?”He gasped and said, “No, that’s perfect!”

He took my little boner between his thumb, index and forefingers and asked me the same question…”I like a lighter touch” I replied and he loosened his grip.

We fell into a rhythmic stroking of each others cocks. Our lips and tongues busily kissing and lapping at each other.

The pressure began to build within my balls. I was getting close and assumed he was, too. My hand moved faster and harder up-and-down his wonderful cock-shaft. He did the same for me.

We broke-off the kiss to fully concentrate on our mutual masturbation. His arm around my shoulder pulled me closer to him and we moved our hands up-and-down canlı casino as fast as humanly possible.

Within seconds of each other, our balls exploded sending rope-after-rope of sperm and semen shooting wildly in the air.

“OH JOHNNY” he cried out.

“ANDY – OH ANDY” I shouted.

Our hands became slick and messy with cum but we didn’t stop frigging each other until we’d milked every last drop of jizz out of each others balls.

When our bodies finally settled down, we kissed again.

“That was wonderful, John…” he said fighting for breath.

“Ohhhh, yes it was!” I couldn’t help but agree; only a handful of guys ever cared whether I climaxed or not.

We cleaned up the best we could then fastened our clothing in place. We kissed and hugged. I was no closer to determining whether he was a ‘top’ or not…oh well – maybe next time…

Outside the car, I entered his phone number into my cell phone, and promised I would call him the following day.

He gave me one last peck on the lips then set out in the darkness to find his own car.

On the long drive home I had plenty of time to think. It wasn’t until I was two blocks from home when I asked myself, “I really like Andy – what difference does it make if he’s a submissive, too?”

The next morning at work after I’d changed into my uniform I hesitated then walked back into Ally’s office.

I would be having my first ‘training session’ with Billy that night for my sessions with the mysterious ‘Mister X’ and I decided to ask Billy his opinion about whether I should ask Ally for permission to date Andy.

Don’t be such a weenie, John, I said to myself, and marched into his office to ask him directly.

He showed no emotion when I asked him. I guessed this wasn’t the first time he’d heard this request.

“You must obviously like him to be asking me this…” he said.

“I like him a lot,” I answered truthfully.

“I don’t have a problem with it as long as you two are discreet and it doesn’t interfere with your work,” he said.

Oh my goodness, that was easy. I breathed a sigh of relief.

“Does he like you as much as you like him?” he asked.

I was momentarily speechless. “Well, I, uh, yes, I think so,” I finally said.

He continued: “Now I only ask that because it reminds me of an old saying my mother once asked my sister – why should a man buy the whole cow if he gets the milk for free?”

I understood what he meant, and said, “No, no…he really does like me…at least I think he does…”

A sad smile formed on his lips. “John, you should find out ASAP what his intentions are…I can’t tell you the number of times around here a boy has gone into what he thinks is a relationship, but in actuality, the man simply wants sex without having to make a donation to your college fund.”

“Uh, yeah, I can see that happening,” I said, “but Andy is different – I’m pretty darn sure he likes me for who I am.”

“Let’s assume that is true. There a couple other things I should make you aware of, okay?” he asked.

I nodded.

“We’ll say he likes you as much or more than you like him…he already knows what you do, and he says he’s fine with it – that it doesn’t bother him at all…well, more times than not your boyfriend will begin to change his mind…he’ll complain he doesn’t see enough of you – that you spend more time working than with him…gradually your conversations will evolve into ‘So, what did you have to do today at work?'”

He slowly shook his head as he continued. “If you don’t give him 100% attention, he’ll begin to say things like ‘Oh, you like those guys better than me’ or ‘Are their cocks bigger than mine?'”

“I, uh, Ally, I don’t think Andy will be like that,” I said.

“Hopefully not, I simply want to point out what other boys have gone thru…after awhile, it is pretty much a certainty he will be so consumed with jealousy he will ask you to quit, or he will leave you…and even worse, if he doesn’t say anything, his behavior towards you will drastically change…he will become cold and distant, and will use you for sex only, and quite possibly either verbally or physically abuse you…I’m just saying John, go into these types of relationships with open eyes and clear thinking!”

“I will…I really do think he likes me for who I am…but I know what you’re saying and I’ll be careful,” I said.

I called Andy that afternoon and said, “I know a guy who has a huge crush on you – would you like to go out on dates with him?”

“You mean that skinny old man where you work? That would be great – he’s really a hottie!” he replied.

Once I finished laughing, I said I couldn’t see him for a few days and made a date to meet him at ‘our restaurant’ on Saturday night.

He said he understood, and would be looking forward to our date all week long.

I didn’t know what kind of ‘training’ Billy would put me through to prepare me for Mister X (Billy wouldn’t tell me the man’s name – only that he is one of the richest men kaçak casino in the state, and extremely private).

As soon as I was in his apartment he told me to strip. Then he handed me a rubber bag with a nozzle on it. He laughed at the expression on my face.

“C’mon, we’re going to the bathroom, I’ll show you how to use this,” he said.

Well, yes, I’d heard of enema’s before, but never had the pleasure(?) of having one.

“Get used to it,” he said. “Mister X’s assistant will be giving you one of these every time you go there!”

Oh my goodness…

He explained when I get to the small house where we’ll be meeting, Timmy, the assistant, will give me first an enema then a bubble bath; and he’ll examine every inch of my body to make sure I am hairless.

“You think your body is soft and smooth now?” he said. “Well, you will be required to soak in a bubble bath once a day for thirty-minutes…Timmy will give you a bottle of the bath soap…I know you prefer showers, but you will come to love sitting back in a nice hot bath.”

“This Timmy person, what is he like? He’s going to be doing some very personal things to me,” I said.

“Well, yeah, it comes with the job…he’s an older queer who’s been with Mister X for years…he was probably the old man’s ‘original’ butt-boy,” said Billy. “And yes, you’ll be having sex with him, too…just do whatever he says and you’ll be fine.”

Once I was ‘cleaned-out’ I followed Billy back into the living room. He had me stand at one end of the sofa.

I saw on the table, a pair of small, steel balls attached to chains with clamps, and what I recognized as a butt-plug. Oh my goodness…

Wasting no time, Billy picked up the steel balls, attached the clamps to each of my nipples…he gently lowered them then released them and I felt them tugging at my nipples.

“Oh my goodness,” I exclaimed when I felt the pain of my nipples being stretched. “What do these weigh? Two-three pounds?”

Billy chuckled and said, “Yeah, I know…the first few times they really do feel that heavy…actually they only weigh five-ounces…you’ll get used to them after awhile.”

“Okay, bend over and place your arms on the armrest…good…now open your legs wide – no wider…that’s good,” he said.

He took the butt-plug from the table and stood behind me.

“Each night we’ll use a little larger plug…by the time we’re finished, you will be able to take Mister X’s cock much easier…busting your cherry won’t hurt him, and it’ll make it more pleasurable for you!”

‘Busting my cherry’? The stark reality of my immediate future caused a cold shiver to race up my spine.

He had oiled the plug, and had little difficulty inserting the small head past my anus and inside my asshole. I was confused and embarrassed when my prick instantly stiffened.

Billy chuckled and said, “That is a good thing – you’ll want to enjoy it when he fucks you.”

“Okay, it’s 7:25,” Billy announced. “You have one-hour – try not to move too much or those steel balls WILL feel like they weigh two pounds!”

I did my best to remain perfectly still, but it didn’t take long for the pain to become almost unbearable. My upper body began to move causing the steel balls to sway back and forth – OH MY GOODNESS IT HURT…I closed my eyes and concentrated on not moving at all…that somewhat helped.

It was the longest hour of my life. Billy had gone to his bedroom and I heard the television blaring. Whatever show he was watching, I found listening intently to the dialogue took my mind off my predicament.

I was in a far-off zone when I felt the plug being removed from my ass. He reached for the nipple clamps, and before he unfastened them warned me, “When I open the jaws of the clamps, I’m afraid you’re going to feel some real pain for a few seconds.”

OH MY HELL IT HURT…I cried out a short “OH” – grit my teeth and waited for the pain to subside.

Billy sat on the sofa. He was now wearing only his boxers.

“Another fifteen-minutes and you’ll be done!” he said as though it were a good thing.

“Sit on my lap facing forward!” he ordered.

When his hands began to pinch and pull at my nipples I almost jumped off the sofa.

“BILLY,” I cried out in pain.

“I know, I know – just ride it out, sweetie…” he said. “Haven’t you ever wondered how my nipples became this large?”

Oh my goodness – I hadn’t thought about it. I’d always assumed he was born that way.

“I know how much it hurts – I went thru the same thing…but I promise you by this time next week you’ll love your new look…not only that, but your nipples and breasts will become a major erogenous zone too…anytime someone plays with your titties and nipples you’ll get an instant hard-on…you’re going to love it, sweetie!” he declared.

My only thought was ‘What is he turning me into?’

For fifteen-minutes, he ‘exercised’ my breasts and nipples all-the-while explaining my role with Mister X. How I should act – what I should say…this would be our pattern for the next five-nights…ever-larger butt plugs in my ass and painful stretching of my nipples.

I called Andy each day after work. The sound of his voice comforted me…and helped me endure the pain I knew was coming every night.

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