Copyright © Tim Hobson - all rights reserved.
Tim's entrée into the world of anal sex leaves him unfulfilled and discouraged, but Beau assures him that nothing is wrong. Their visit to an adult toy store is totally embarrassing for Tim, but he recognizes that Beau is a pro who will take him where he wants to go sexually with great care and affection.
Please note, I am a poor user of copy-and-paste. This is truly Part 8, and Monday's was actually Part 7, even though it was called Part 6 in the title. I'll try to be more attentive to details...
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GOING GAY - PART 8
["No, asshole." I grinned, mussing his hair, "Anal sex!" And with that, we raced into the bedroom.]
We undressed in a flurry, flinging what little clothes we were wearing in every direction. As we poised at the bedside, Beau looked into my eyes and asked seriously, "Just to be clear - you're going to fuck me, right?"
"Is that what you want?"
"Fuck, yes! I just want to make sure, because you're not ready to be fucked yet."
Indignantly, I countered, "and how the fuck do you know that?"
"Because you're a virgin, and it takes a whole lot of prepping before your first time, which we have definitely not done yet." I shrugged my shoulders and said OK, eager for my next lesson.
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 dueling 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 come!" 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 assholes, 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 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 that 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, the tube of Swiss Navy® in it. I sighed with relief, accepted the tube and positioned it as I had learned, just above the top of Beau's crack. I squeezed it, intending to mimic Jimmy's polished application, and suddenly 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 was so great. 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 - 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 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 tiny load of come 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 said, "Just leave it there, OK? And don't worry. Plenty of guys come quickly the first time. This is something new and you've not had time to learn how to make it last. Don't worry - you will."
We stayed in that position for a while, and then suddenly 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. 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 asshole 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 virgin 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 step-wise 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. Then Beau guided me off the island and deep into the eastside neighborhoods of San Diego. We finally stopped 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 magnitude 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. "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."
"Ouch!"
"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 fifteen minutes or so. That way, you know that you can take that size 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 'teen-age 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 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 check-out: 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 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 school-boy!" I exclaimed.
"Me too, and I'm a fucking professional," Beau agreed, adding "and a professional fucker!"
Roaring with laughter, we made a bee-line for our suite and I only relaxed once the front door was shut and locked.
Stay tuned to https://www.nifty.org/nifty/gay/beginnings/going-gay/ for the next installment!