Going Gay / Tim – Chapters 13 – 16


Naked, we jumped onto the bed from opposite sides, lay down and quickly entwined our bodies, kissing passionately. We were both already hard and as we writhed, our cocks fencing like swords between us.

Knowing that the previous “lessons” from Beau were a necessary part of foreplay for the main event, I began stroking, then sucking his beautiful eight-inch cock. We slipped into the 69 position and pleasured each other for a while. In previous cock-play, I had discovered that Beau loved it when I paid special attention to his foreskin. I would suck on it, pulling it all the way down past his cockhead, twirl my tongue inside it, and then push it back down as far as it would go. The back-and-forth motion of the foreskin over his helmet almost brought him to orgasm a couple of times.

“Hey, you better cut that shit out, or you’re gonna get a mouthful of cum!” he would squeal and giggle. And more than once, that’s exactly what I wanted from him, so I kept going and he proved true to his word!

After a little while, Beau rolled up onto his elbows and knees and crouched over me, taking my hard prick in his mouth and lowering his into mine. We had used this position many times to tease each other’s buttholes, but this time, teasing was going to be only the first step. I began to quiver with anticipation.

“Are you OK? Are you cold?” My lover inquired.

“No, just so fucking excited. I’ve been wanting and dreading this moment for a long time.”

“Why dreading?”

“Well, what if I can’t please you or satisfy you? What if I get inside you and you can’t feel a thing? I’m not ‘Jimmy Fucking-ten-and-a-half-inches Coxx’, after all!”

Beau laughed heartily. “No worries there, Tim. You’re a lot bigger than many who’ve been in there, and I’ve never had any problem getting off, no matter what the size. Remember, the greatest pleasure comes from a tiny spot smaller than your thumbnail. As long as you hit that with your pecker, I’ll have a great time!”

“Great. Now I have something else to worry about!”

“Quit fucking worrying and pay some goddamn attention to my horny ass, please!” With that, we both laughed, and I relaxed. In my mind, I knew that I only wanted to please my lover, and any fear that I might not be able to do so was something I’d just have to conquer.

And with that, I attacked his pucker enthusiastically with my tongue and fingers, working it up, down, and sideways, inserting one, then two, then three fingers and twirling them around inside him. He moaned with pleasure.

When he was ready, Beau moved off and allowed me to get up. He assumed that “doggie” position with his beautiful globes enticingly pointed at me, arched his back, and wiggled his ass a little. I giggled.

Then, remembering how Jimmy had shown his appreciation for Beau’s bottom, I spread his cheeks wide with my hands and buried my face deep into his crack, greedily tonguing his hole. Once again, I was astounded at how clean and free of any unpleasantness it was. I made a mental note to ask him how he accomplished this, but that would be for after.

Once his backside was fully wet with my saliva, I remembered the lube. I lifted my head in panic, glancing furtively at the drawer of the bedside table. Without a word, Beau extended his left arm back in my direction and handed me the tube. I sighed with relief, accepted the lube and positioned it as I had learned, just above the top of Beau’s crack. I pressed the plunger it, intending to mimic Jimmy’s polished application, and all at once a monstrous glob of goo spurted out – about ten times the needed amount, splashing all over Beau’s back, his ass, and onto my face!

Beau roared with laughter, rolling around on the bed holding his stomach in hilarity. I was totally humiliated, but his laughter was contagious and soon I was laughing as hard as he was.

“Well, so much for Anal Sex 101,” I said in mock disappointment. “I guess I’m sent to the back of the class now.”

“No, goddammit, you’re sent to the back of ME, and I have a feeling that we won’t need any more lube today.” With that, he resumed the doggie position and tantalizingly shook his ass at me. “Now, fill ‘er up, please!”

I was amazed to see that, through all the foolishness and embarrassment, my cock was still fully hard, my desire for him so overpowering. I moved closer to Beau’s ass and lightly rested my rod between his cheeks, like a hot dog in a bun. That set me to giggling. I had a wiener between Beau’s buns! But Beau assumed I was just having a good time and said nothing.

I began to slide my dick up and down the slippery ass crack, and the sensation got me even harder.

“Any time…” Beau said chidingly.

“You asked for it!” I said, aiming the head of my prick at his hole and pressing lightly. I felt resistance and hesitated.

“Don’t worry, you can’t hurt me. Just keep pushing, and it’ll pop in.”

With that, I went for it, applying gentle pressure until I felt my helmet pass one, and then two, rings of interior muscle.

It instantly felt like I had entered a hot, soft, wet cavern that thoroughly surrounded and gently massaged my dick from all sides. Having been married for 50 years, I knew exactly what a vagina felt like, but this was different. Vaginas are roomier and, once inside, my dick sometimes lost contact with the walls.

Beau’s rectum was soft but tight, and I wondered if he was intentionally contracting it in order to squeeze my cock, or if this was just how it behaved. I made another mental note to ask about this at a more opportune time.

I eased in until Beau’s butt cheeks rested on my pubes.

“That’s all I’ve got, Beau.” I said apologetically.

“Fucking fantastic, Tim-oh-thee! It’s more than enough. Now for shit’s sake, please start fucking me!”

With that, I began a rocking motion, gradually increasing the tempo until my thighs were slapping his ass loudly. I was just thinking about trying the “pull almost all the way out and then pound in deep” routine that I had seen Jimmy use, when a familiar but unwelcome feeling overcame me.

“Oh, shit,” I exclaimed, as I completely lost control and frantically pumped my paltry load of cum deep into Beau’s beautiful hot ass. “Fuck! FUCK! I’m sorry! It just got away from me.”

I started to pull out, but Beau quickly stopped me, saying, “Just leave it in there, OK? And don’t worry. Plenty of guys cum quickly the first time. This is something new and you haven’t had time to learn how to make it last. Don’t worry, you will.”

We stayed in that position for a while, until finally my soft dick slithered out of him of its own accord. It felt like the ultimate defeat. I sat back on my knees and looked up at the back of Beau’s head. He rolled over and gently pulled me onto him. I rested my head on his chest and breathed softly. He was caressing and consoling me, which only made it worse.

I sat up and looked him in the eye. “Listen. I know I’m too old to please you the way you want. I KNOW that. So please understand that you can find your pleasure and satisfaction anywhere you want to. I won’t object, and I won’t be jealous,” I said this last with a crack in my voice.

He pulled me back onto his chest and held me as I sobbed softly. “Listen to me, Tim. You are NOT too old. You are a man of a certain age, and your body works the way it was intended to at your age, and very well at that, I might add. I have always known that, and you’ve never had any trouble satisfying me.”

Beau kissed me lightly on the top of my head. “I don’t need anybody else or any other lover to make me happy. So what if you came a little too soon this time? Now you know what it feels like inside there, and you can control your progress the next time, just like when we’re sucking each other. It’s an acquired skill, so it’s no surprise that the first time was not what you had hoped. There will be plenty more times, I promise!”

We cuddled for a long time. Then I rolled onto my back, and said, “Well, my half of the lesson kinda fizzled, but there’s still your half.”

“My half?”

“Hell, yes. I want you to fuck me.”

Beau was silent for a while, then he began, “Tim, like I said, that’s a tall order. First of all, your ass is virgin, if I’m not mistaken?”

“Of course,” I said with regret.

“So that means we have to work up to it gradually. There are a half a dozen or more intermediate steps we have to go through before I can plow your cherry ass with my big, hot, horny dick!”


We both laughed at his crudeness, but I was aching with a mix of curiosity and apprehension. “What steps?”

“Well, for starters, we have to gently and gradually stretch your hole open, so that something bigger than your doctor’s finger will fit inside.”

“How do we do that?”

“OK. You and I will get dressed and take a little drive. I know a place that sells all the necessary implements.”

“You mean a sex store?”

He giggled at the term. “Yes, more politely known as an ‘adult playthings emporium’! We’ll get all the necessary stepwise accessories and bring them back here. Then, we’ll take things slow and make sure that you’re 100% comfortable at each stage before going on to the next. It could take a while, or you might get used to it quickly. A lot depends on your anatomy, and we can’t change that.”

And that’s what we did. We showered, dressed, and called for my car from valet parking. As I drove, Beau navigated us off the island and deep into the eastside neighborhoods of San Diego. We finally arrived at a strip mall with a number of curious-looking businesses in it. There was a liquor store, a vaping shop, a lingerie boutique, a pawn shop, and a couple of businesses that it wasn’t quite clear what they were. When I asked, Beau simply said, “weed.” At the end of the row was our destination: The Adult Fantasy World.

We entered, and I was blown away by the plenitude of clothing, videos, magazines, and sex toys and aids openly displayed for anyone to see. Looking back at the entrance, it hit me that the doors and windows were all covered by brightly-colored posters, so no one on the outside could see what was available or being purchased within. There was also a curtained door at the rear.

“Where does that go?” I asked innocently.

“Video booths. You know: porn!”

I blushed. I had never lived down the disparaging remark that I once made about porn, completely forgetting that Beau was a star in that entertainment venue.

“Maybe I’ll take you back there and introduce you to some of my biggest hits some day.”

“You know, I’d kind of like that.”

“Well, not today. We’re here on a mission.”

“Yes, sir!” I snapped a salute. “So, what instruments of torture do I need today?”

He gave me a disapproving look. “Listen. If anything hurts, you tell me, and we stop immediately.” Beau said sternly. “I don’t want blood all over those beautiful satin sheets on our bed.”

“There can be blood?” I said apprehensively.

“Not if we do everything right and take our time. Don’t worry, you’re in the hands of a pro.” He smiled and gave me a quick kiss on the cheek.

With that, we proceeded to select our purchases, or rather Beau selected them as I watched in wonder and growing trepidation. He explained each item as he selected it.

“This is a butt plug. As you can see, it starts out very small and gradually gets wider and wider. It will allow you to ease it in as far as you’re comfortable with, and then try for a little deeper the next time.”


“Like I said, we will do this the right way, so as soon as it’s uncomfortable, we stop. But you should leave it in at that depth for a while. That way, you know that you can take that size again the next time and try for a little more.”

After that, Beau moved to a rack of big pink rubber or plastic penises. I noticed that there were several sizes. “We’ll start with a ‘teenage boy’ size, and once you wear that out, we move up to man-size, and maybe someday to Jimmy-sized!” He said with a grin, pointing at a humanly-impossible monster.

“Oh, I doubt I’ll ever get that far!” We both laughed.

“Well, fortunately, I’m nowhere near that big, so if it’s me you’re lusting for, we won’t ever need the humongous size.”

We were laughing so much that the store clerk looked up to see if we were up to no good. We immediately got serious and moved to another aisle. There, Beau picked out a vibrating dildo. “The vibrations take your mind off any discomfort, and they also help it slide in more easily.”

We also bought something that embarrassed me when we took it to the store clerk for checkout: a two-foot-long dildo with a cock head at each end. Beau simply picked it up, gave me a look, chuckled, and put it in our cart. I had no doubt what he planned to do with that monster.

All told, we spend over $250, and I was careful to pay with cash. I didn’t want my friend and accountant, Keith, to see the charge on my credit card bill.

Once outside, I felt like I needed to make a mad dash for the car. I knew we weren’t breaking any laws or doing anything that any other customer of the store didn’t do, but I was still red-faced with embarrassment and terrified that someone I knew would see me. This was completely irrational, because I didn’t know anyone in San Diego except the guys I had met at the hotel.

Returning to the Del Coronado, I surrendered the car to the hunky valet. As Beau retrieved the large pink-striped bag with “Adult Fantasy World” in bold purple letters on it, the valet attendant grinned and winked at him. I blushed again, and, seeing my discomfort, Beau quickly diverted us away from the front entrance of the hotel to a narrow walkway leading to a side entrance and then directly into the elevator. I breathed a deep sigh of relief and then we both burst out laughing.

“I feel like a naughty schoolboy!” I exclaimed.

“Me too, and I’m a fucking professional,” Beau agreed, adding “and a professional fucker!”

Roaring with laughter, we made a beeline for our suite and I only relaxed once the front door was shut and locked.

Once inside the suite, I felt like a little kid on Christmas morning! Even though I had seen everything we purchased, I had done nothing more than watch as Beau examined and selected the “tools of the trade.” I couldn’t wait to handle them myself and began popping them out of their plastic cases.

“Hey, slow down, buddy!” Beau exclaimed. “You’ll have plenty of time to get to know these babies.”

I took a deep breath and sat back.

“The worst thing you can do is rush this, Tim. These are meant to be used in a certain order, so that you gradually increase your ability to take them up your ass,” he said with a wicked laugh.

Laughing shyly, I demanded, “When can we start?”

Beau stood and said, “First things first. Step into the bathroom with me.”

Once there, he opened a drawer in the vanity and removed a small cloth bag. I was mystified and more than a little nervous.

“What’s that?” I barely squeaked.

“Well, you once asked me how come you didn’t see or smell anything nasty when you were tonguing or fucking my ass… This is why. It’s called an enema.”

He removed an object about 8 or 9 inches long. The bottom of it was a round purple bulb with a flat bottom. The rest of it was a black tube about six inches long, straight, but with a little curve in the last inch. Next, he took out a small red bottle, holding some kind of liquid, I presumed.

He held up the enema. “This serves two purposes. First, we put warm water in it and wash you out completely. Then (he held up the red bottle) we put this lube inside you. It helps things a lot.”

“I thought you used the lube on the outside?”

“We do, but that’s just to ease the entry. On the inside, the tissues are sensitive and easily bruised, so this is both a lubricant and a medicine that anesthetizes your insides. That can help prevent any damage the first couple of times.”

“Damage!?!” I exclaimed with horror.

“Well, not any real damage, but the skin on the inside has never been jabbed and rubbed like it’s going to be, so until you’ve done it a few times, it’s not unusual for the skin to bleed a little. After you get used to it, you’ll enjoy it even more if you switch to a non-numbing lube. That way, you’ll feel everything good that’s going on inside there. But we always start with this kind,” he said, waving the bottle in front of me.

“You said there’d be no blood!” I accused him.

“Not if we go slow enough and do everything right, but right now you seem hot to trot, so I’m worried you’ll rush things. And if you do, a little blood is the price you’ll pay. It won’t be serious, and it will stop right away, but it’s not unusual for a virgin like you.”

I thought back to the first girl I had ever fucked. A virgin, she also bled a little when we did it. “OK. That makes sense.”


I looked at the bulb and bottle for a moment, thinking. Then I cautiously began, “There’s another thing I’ve been wondering about…”


“Well, I don’t know how to say it, but… you never use a condom.”

Beau looked serious for a moment. “No, I don’t, but you can any time you want to.”

“Do I need to?” I said, not looking him in the eye.

“Well, for peace of mind, I would say ‘yes, if you want to’, but for health and safety, then the answer is ‘no, you don’t need to’.”

“How so?”

“So, you already know I do porn flicks.” I nodded. “And these days, anyone who appears in porn without using a condom has to have a blood test 30 days before each performance and again 30 days afterward. That pretty much rules out any kind of STDs, including HIV. As long as the models don’t have sex with anyone else, or at least use protection if they do, then the studio can assure the audience that they have been thoroughly tested. Even with all that, every porn film begins with a warning to always practice ‘safer’ sex, which means a condom or some other way of not sharing fluids.”

“How effective is all that?”

“Hmm. Well, so far I have never heard of anybody coming down with anything if they follow the protocol faithfully, and every studio, or every reputable one, makes damn sure all their models follow the rules, or they’re out.”

“So, you and Jimmy…?”

“We made a video together two weeks before you met me, and we’d both been tested before and after, so I was comfortable letting him fuck me yesterday.”

“But what about me? I didn’t get tested.”

Beau looked me in the eye seriously “Do I have anything to worry about?”

“I guess not. I haven’t had sex with anybody before you for the past two years or thereabouts.”

“Well, Tim, I think it would be a good idea for you to get tested, just for your peace of mind. It’s nothing to rush, but I gotta assume you won’t always be doing me.” He smiled, “And my ‘clearance’ will run out in a couple more weeks.”

“Is that all the time I’ve got left with you?”

“Fuck no, baby! I just meant that the window of safety is only 30 days long.”

“Aren’t you going to make another porno soon?”

“I haven’t heard anything. You see, the way the studio works is they call me in for around two or three weeks of taping. I fuck just about every other day until they have all the film they need. Then it goes into postproduction, where I usually get called in to do ‘looping’, which means recording my voice over the video. Then they edit it and smooth out the rough spots until they’re ready to release it. And that takes another three or four weeks, so they don’t call me back until all that’s done.”

“Why not, if you’re so popular?”

“Good question. I guess they don’t want to flood the market and have the audience get tired of seeing me.”

I nodded my understanding, and Beau smiled: “Now, if you don’t mind, get naked for me, please.”

I complied and Beau also stripped and led me into the shower. With a warm, gentle stream running over us, and especially down my back, Beau demonstrated the use and application of the enema bulb. First, he pulled the shaft out of it and held it under the shower stream, filling it with warm water. Then he popped the tube back in place.

“Now, bend forward about halfway.” He told me.

As I did so, I felt him massaging my ass cheeks. I felt the stream of warm water from the shower head running down my back and right into the crack and felt him gently slide one finger inside my hole. He twisted it around a couple of times and then pulled it out. Immediately, it felt like he put it back in, but I could feel it move deeper and deeper inside me.

“Is that…?” I asked, my voice quavering.

“Yes, my lover, you now have a fucking enema all the way up your sweet ass! Does it hurt?”

“No, not at all.” As I was saying that, I felt a gush of warm liquid fill my rectum. It felt like it was full to bursting, and I had an almost uncontrollable need to push it back out. Beau interpreted my facial expression. “Don’t worry. Just let it stay there for a few more seconds.” Then I felt it all being sucked out rapidly.

“That’s all there is to it,” Beau explained, as he squeezed the bulb empty onto the floor of the shower. “Now you try it.”

I copied his actions, removing the bulb and filling it with water. I had a bit of trouble aiming it at my pucker, so Beau helped guide it in. I squeezed and once again felt that uncomfortable urge to shit. I counted to ten, which was about how long it seemed that Beau had waited, and then squeezed the bulb again, drawing the water out. When I removed the bulb and dumped it, I was pleasantly surprised to see that it was nearly clear.

“You’ll need to do that until the water is completely clear, two times in a row.”

“You do this every time you have anal sex?”

“Well, yes and no. If I’m expecting to do it and have time to get ready, I do this.” He pointed at the enema bulb.

“You mean sometimes you’re not expecting it?”

He smiled widely and winked at me. “There are times when the passion of the moment doesn’t allow for proper preparation.”

“What happens then?”

“Well, it depends on the time of day. Without getting into anything too disgusting, I usually empty my bowels first thing in the morning, and that’s it for the day. As long as that works, there isn’t really anything much left behind, so it’s almost unnecessary to clean out.”

Seeing the expression on my face, he hurried to add, “But it’s always polite and advisable to take the time to rinse, out of respect for your partner. Nobody likes to have wild butt-fucking sex and then pull out with ‘brown’ on their dick.”

I grimaced. “That’s so fucking gross!” We both laughed.

I repeated the cleansing process two more times, and the water came out clear both times.

“Looks like you’ve done a good job. Now, the next step…” We got out of the shower, toweled off, and Beau faced me, holding the little red bottle. “As I said, this helps lubricate and numb your insides a little.” He showed me how much of the liquid to squeeze into the bulb, replaced the funny-looking tube with the little crook at the tip and told me to sit on the toilet. “Now just raise your ass up high enough so you can get your hand and the bulb back there. This time you’ll have to find the hole without my help. Push the stem in and squeeze gently. You shouldn’t feel like you have to go this time, because there’s only a tiny amount of liquid there.”

I did as he instructed, and said, “It doesn’t even feel like anything went in.”

“I’m pretty sure it did, so now just pull the stem out and immediately squeeze your asshole shut tight, like you’re trying not to crap. Then just sit on the toilet for a couple of minutes. If there’s too much in there, a little might dribble out, but that’s OK because enough will have been absorbed by then.”

Beau then took out the bright pink butt plug thingy. He proceeded to run hot water in the sink and then to wash the sex toy thoroughly with soap and water. “That’s all it usually needs, although you can also wash it with rubbing alcohol if it makes you feel better.” He dried it on a hand towel.

As I sat, I thought how foolish I looked, naked, sitting on a toilet in front of my lover, who was also naked (and by the way, starting to get a hard-on!), waiting for something to dribble out of my ass! I laughed out loud and felt a little hot liquid dribble out.

“Oh, shit!” With that, the rest of the enema squirted into the toilet.

“Definitely not, and I told you that any excess would come back out, so you’re doing fine. Now let’s head for the bedroom,” Beau said, picking up a clean towel.

“What’s that for?”

“Just in case we make a mess the first time.”


We got onto the bed. I lay on my back with the towel under me from my lower back to my knees. I was curious why Beau had remained naked, but I didn’t say anything about it.

“Now, spread your legs a little and lift them up and pull your knees to your chest.”

As I tried to comply, Beau laughed. “You’re not trying to break your back, are you? Just relax. All you’re doing is showing me your hole and keeping your legs out of the way. Just fucking relax!”

I took a deep breath and got more comfortable.

“Now, as I said, we have to start small,” Beau explained as he picked up the butt plug. “So all I’m going to do this time is ease the tip of this baby inside you. If it hurts, tell me right away.” With that, he smeared a dab of lube on it and aimed it at my fuck-hole.

I braced myself for searing pain, but all I felt was a tickling on my pucker and then a slight pressure. I felt the plug push through a ring of muscle and then Beau stopped.

“All right so far?” I nodded. He went on, “Your ass has two rings of muscle, an outer one and an inner one. They’re close together, but you will probably feel like they’re a mile apart the first few times. We just crossed the first hurdle!” He chuckled. “Now, here’s the second one.” I again felt the pressure and a sensation when the plug passed the hurdle.

This time I felt like I had to go. I squirmed.

“Did that hurt?”

“No, but it feels like I have to shit.”

“That’s normal. For however many years, your body has been trained to interpret pressure on that inner ring as a signal that you need to take a dump. You’re now teaching it that there’s another reason for that sensation. We’re just going to stay like this for a few minutes, and you should soon feel nothing unusual at all.”

Beau was right, after a short while, the urge to defecate was gone, and I just felt something small and not at all unpleasant occupying the entrance to my ass.

“I think I’m good now,” I told Beau, looking into his face for reassurance.

“You fucking are, buddy!” He applied a little more pressure and I felt the little pink thing grow slightly. He waited about a minute and then pressed a tiny bit more.
“Doin’ OK?” I nodded again. He repeated the process again, and I felt like my hole couldn’t stretch any further.

“That’s about all I can take,” I said, trying not to sound like I was in pain.

“No problem. You’re doing fucking great for the first time!” He held it in place for a short while, then slowly and gently withdrew the plug. I had to look and was greatly relieved to see no trace of either brown or red on it.

“How do you feel?” Beau asked.

“Like I’ve been fucked.” I said, snickering.

Beau laughed, “Well, you’ve been stretched a little is all, but I have to say you took more than I thought you would for the first time.”

“So, now what?”

“Just rest a few minutes, and then we’re going to do it all over again.” My face must have told him I wasn’t exactly thrilled with the idea. “Tim, what we’re doing is slowly but surely stretching those muscles, so that, someday, something very nice can get in there, and we can both have a great time.”

I sighed, “I know. This is just not quite what I thought anal sex was going to be.”

“Baby steps! That’s the safest and most comfortable way to get there.”

“How long is this going to take?”

“Depends on how you feel, and how eager you are to make progress. If we do this just once a day, it could take weeks.”

“Get with it then, goddammit!”

With that, Beau slowly and tenderly repeated the process of acquainting my tight old ass with a welcome intruder. I can’t honestly say that I enjoyed any of it. There was no real pain, but the strange feeling didn’t get any more pleasant with repetition. He did it a total of four times, and then he took the butt plug into the bathroom as I cleaned myself up with towel I had been lying on, being extra careful not to stain the bedsheets in any way.

“Come in here and get cleaned up,” Beau called from the bathroom, as I heard him turning the shower on. When I entered, he was already under the water with a hard-on.

“Turned you on doing that, did it?” I teased.

“What turns me on is the thrill of seeing you experience a sexual pleasure that you have never felt before. That, and the thought that it won’t be long until my dick is right where that butt plug was today.”

With that, he drew me into the shower and into a passionate embrace. He lovingly washed me from head to toe, then knelt before me and took my erection into his hot, wet mouth. To my surprise, and in spite of the assault on my backside, I found that I was horny as hell and quickly came in his mouth.

After swallowing, Beau looked up at me and smiled. “I knew that was turning you on. I don’t know why, but there’s a direct connection between ass-stimulation and horniness. I guess that’s just the way we’re made.”

He rose, and I kissed him deeply, then knelt down and returned the favor. As the warm water flowed over our naked bodies and his hot cum filled my throat, I felt the first twinge of true love for this beautiful young man who was so committed to my sexual enjoyment.

My next lesson, after dinner, involved taking the butt plug what seemed like several inches deeper into my tight hole, but I know it was really only a tiny bit deeper. Before I allowed the instrument of “torture” to invade my posterior, I asked Beau, “how big around is that fucker?”

“At the base, where you won’t EVER need to go, it’s probably eight inches around. Jimmy’s fuck-stick is six inches, and that’s pretty goddamn big! My dick is about five, and yours looks like it’s probably four or four-and-a-half.” As he spoke, he showed me places on the length of the sex toy that corresponded to the sizes he was naming.

“If nobody is eight inches around, why is this fucking thing that size?”

Beau hesitated, looked down, and then up again with a sly grin, “Tim, Tim, Tim! There’s a whole other world out there, and there are people and places I hope you’ll never know about…”

“Come on, just fucking tell me, goddammit!”

“OK, but just don’t go getting any ideas.” He took a deep breath. “There are people, men I mean, who enjoy pain and taking things to the extreme. While no natural penis is eight inches around, the pain-slash-pleasure of having something that fucking big up your ass does have a certain attraction to some guys. It’s not really healthy, either physically or mentally, but there you have it. Some guys are into pushing their limits. They’re usually high on something when they do it, to mask the pain.”

I was silent. I didn’t want to appear shocked or disgusted. I have always known that there are people with strange sex fetishes, and I’d heard jokes about the kinds of things that some guys will try to shove up their butts: light bulbs, cucumbers, and even other men’s fists, but I was not prepared to come face-to-face with this reality.

I hesitated, “It kind of… seems like… what we’re doing is the first step toward some kind of weird and dangerous twilight zone of kinky sex…”

“Sure, just like drinking your first beer was the same way that the drunk lying in the gutter covered with his own piss and vomit got started. Anything can be taken too fucking far, and from what I know about you, it isn’t even conceivable that you’d end up that way.”

“Or you?”

“Fuck, no! I’ve seen a little of that shit, too close for comfort, and it only reinforces my knowledge of my own limits.”

“You mean, you’ve been asked to do some things like that?”

“Oh, sure. I’ve run into customers and even porn directors who try to see how far I’m willing to go, but once I make my rules clear, the subject is dropped. Can’t blame ’em for asking, I guess.”

I took a long, deep breath and changed the subject. “So, how far did I go today?”

Beau smiled broadly. “Well, student Timothy Hobson, I am honored to award you the degree of ‘Ready for a Teenage Dick’!”

I didn’t understand at first. Then, as it dawned on me what Beau meant, I got a big smile on my face. “You’ve hired a teenager to fuck me!” I chortled with fake enthusiasm.

We both laughed heartily. Then Beau said, “Right, and then we’d both go to jail for that little caper!” He paused. “No, Tim my boy, you’ll have to make do with this lovely pink imitation of what I had dangling between my legs when I was about fourteen years old!” He reached behind his back and showed me the smallest of the fake penises that we had bought.

“And if I remember what you told me correctly, that’s the very age and size you were, the first time you fucked a girl?”

Beau grinned, “Well, the way I remember it, I was a hell of a lot bigger, but you’re probably spot-on.”

“And what did the lucky young lady have to say?”

He mimicked a girlish voice, “Oh, Beau, you’re SOOO big!” We roared with laughter.

“So, if you’re game, let’s try young Beau and see how he fits.”