Part 2…

“Does it hurt?” I asked with a look that gave away the concern I was feeling. Much to my relief, the sissy shook his head no with a smile.

At the same time, his sissy pussy winked around the two fingers that I had inserted into it, then he sighed. As the heat of his moist lining wrapped itself around my probing digits, I found his hard prostate and gave it a tender rub. As if he had no control, Ricky let go of a soft moan, and a surge of ass juice ran across my fingertips.

“It feels really good, Grant,” he sighed, his eyes filled with lust and something more.

His hard, tiny dick was pressed tight to his pubic bone, and from where I was kneeling between his thighs, I could see it jump every time I contacted his pleasure button. His moans gave away the feeling of pleasure that was coursing through his system, adding to a different feeling that the sissy was luxuriating in. It was a feeling that had been building all evening —a feeling that all his dreams were about to come true.

From my position between Ricky’s open legs, I could see every change in his expression, and it was a little distracting. His head rested comfortably on one of the four plush pillows on my queen-sized bed, and a shadow from the oak headboard had been cast over his face, dimming the light of his sparkling, hopeful eyes. I could also see fear in those eyes, but laced with that fear was an unmistakable note of trust, even comfort.

Perhaps that was born of our earlier interaction when I gave the eighteen-year-old his very first orgasm. Or perhaps it was due to the careful way I tended to his powerful emotional reaction to our act, a reaction that I hadn’t seen coming when he first crawled into my arms and dozed off.

I was sitting on the couch, holding Ricky close and studying his face as he slept. He seemed to be having a sweet dream, as evidenced by the sleepy smile that spread across his fresh face as he rested his head on my shoulder and snored lightly. I let my gaze travel down to his soft dick, noting that it was no more than half an inch in its soft state. It was simply resting against his hairless ball sack, and there was a modest ring of pubic hair at its base.

I planted a soft kiss on his cheek. I considered our interaction up to that moment, wondering how I had gotten so lucky, how I happened to visit the personals on Craigslist at the exact moment that the horny 18-year-old was looking for a man to share his evening with. It was all by chance, and yet here I was, holding a beautiful sissy in my arms while he slept in a post-orgasmic haze.

All of a sudden, the sissy’s forehead furrowed and knotted, then his hands moved down to his flaccid dicklette, and he covered up as his head turned side to side on my shoulder. Unsure what kind of nightmare the sissy was having, I slowly rocked his young body and rubbed his back, trying to bring him comfort and, hopefully, help to slay the monsters that were haunting his dreams. All of a sudden, his eyes shot open with a gasp, and he picked his head up off of my shoulders, both of his hands covering his penis and balls.

“Hey, are you OK?” I asked softly, and he sighed with relief.

Then he rested his head back down on my shoulder and drew in a deep breath. “I had a nightmare,” he admitted, his voice steady but somehow still shaken. “I thought my mom and dad found out I was, err, gay and a sissy.”

“Shh,” I urged him, petting his brown hair with gentle strokes. He lay still for a moment, so I decided to ask about his home life. “Would that be a bad thing, Ricky?”

“It might be,” he said quietly. “I just don’t want them to know until I move out, Grant.”

“I understand,” I told him. “Do you think they would have a bad reaction?”

“I think my mom will,” he said. “My dad might not, but I’m not sure. I’d rather just wait for them to know.”

“Coming out can be a touchy thing,” I conceded, and he nodded. “Do you think they might kick you out if they knew?”

“I don’t know,” he said in a quiet voice, and I realized that the sissy was scared of the prospect, so I moved on.

“Well, let’s not worry about that right now, OK?”

“OK, Grant,” he said, nuzzling his head into my shoulder. “Grant?”

“Yeah?”

“You’re the first person that I ever told,” he admitted with a sad smile.

My heart broke for him. “Well, I think you should be proud that you finally told someone,” I said softly, and once again, his words stabbed at my heart like a dagger.

“Nobody in my family would be proud of me for that,” he muttered. “My mom thinks gay people are sick and that they’re going to hell.”

“What do you think?”

“I don’t know,” he said quietly, and then he looked up at me with anguish in his eyes. “Do you think they’ll be able to tell what I did tonight?”

I looked down at the sissy, studying his features closely. His face was colored with stress and guilt over what we had done together. His eyes gave it all away, and I was sure that if he went home with the expression he was wearing at the moment, his parents would surely know that he had been up to something. To ease his mind and try to change his focus, I opted to divert his attention after offering a little reassurance.

“I’d be shocked if they could, Ricky,” I told him, and he relaxed a little. Seeing this brought a smile to my face, so I leaned down and planted another kiss on his cheek, prompting him to smile up at me sweetly. Returning his sweet smile, I asked, “Are you hungry?”

“A little,” he said, grinning up at me as I gently rubbed his back.

“Then let’s go in the kitchen and see what kind of grub we can scrounge up,” I said, scooting him out of my lap.

When he stood up, I took the time to drink in his beautiful body in its nude form. His tummy was sunken and seemed to disappear where his gut met his pelvis. His belly button was still sticking out adorably, and his exposed dicklette looked so delicious to me as it rested against his small balls. He saw me studying his flaccid babydick and blushed, then he turned away from me while he snatched his panty from the back of the couch, then he bent over and stepped into them.

“It gets small when I’m nervous,” he said weakly, almost as if he were apologizing for the size of his dick.

I gave him a sympathetic smile and nodded, realizing how embarrassed he was.

“That dick of yours is always small,” I said with a wink. “But you have nothing to worry about, Ricky,” I assured him. “I’m one of those men who happens to like sissies with babydicks.”

“You like my tiny dick?” he asked, his voice insecure, and I nodded.

“Sure, it’s so cute,” I said, standing up and placing a hand on his bony shoulder. “But not all men will like it as much as I do. Some will think it’s pathetic and call you a loser for having such a tiny cock. But not me.”

“Thanks,” he said with an appreciative smile, and then we walked to the kitchen.

I opened the refrigerator and the freezer at the same time, scanning the cold box for anything of interest to the sissy. Being single affords me the opportunity to do many things. One of those things is the opportunity to buy only food that I like, including corn dogs, tater tots, Hot Pockets, and ice cream. As soon as Ricky spotted the bounty of junk food in my freezer, his eyes lit up, and he broke into a smile.

“You see anything you like?” I asked, and he nodded.

“Is it OK if I pick more than one thing?” he asked sheepishly, and I rolled my eyes with a smile.

“You can pick as many things as you’d like, Ricky,” I assured him.

The hungry teenager quickly selected pepperoni pizza, Hot Pockets, and tater tots. I pulled them from the freezer and preheated the oven. While I was digging a baking sheet out of the cupboard, I saw Ricky lean against the counter and place the flat of his palms on the surface as if he were contemplating lifting himself so that he could let his feet dangle. When he saw that I spotted him, he blushed and stood up straight.

Unable to resist the urge, I wordlessly approached him and grabbed him by the rib cage with both hands. I effortlessly lifted him and placed him on the countertop. He smiled shyly and looked down, then he said, “Thanks, Grant.”

“You’re welcome,” I said, reaching out and ruffling his brown hair. “You know, you don’t have to walk on eggshells. Just relax and be yourself.”

“OK,” he said bashfully, and he looked so adorable that I had to lean in and plant another kiss, this time on his luscious lips. He grinned mischievously at me this time and said, “If you hurry up and put the food in the oven, maybe we can do that some more.”

With that, he raised his eyebrows at me, so I gave him a wink and returned to work, setting two Hot Pockets on one end of the baking sheet and some Tater Tots on the other. It was almost perfect timing because no sooner had I placed the remaining tater tots back in the freezer than the oven finished preheating. I slid the pan into the oven and set the timer for 20 minutes, then I turned my attention back to the panty-clad sissy who was sitting on my counter.

I approached him with a smile, ready to make the first move, but he surprised me by wrapping his arms around my neck and tilting his head to the right as he leaned in and kissed me right on the mouth. I let my lips part, and his tongue pushed straight through them. And with a moan, he treated me to a make-out session that put us on the path to our final stop.

As our make-out session kicked into gear, I ran my hands all over his warm back, then down to his buns. I slid my fingers between his panty-covered bubble butt and the tile he was sitting on, then I started to squeeze his rump with both hands while he moaned into my mouth. I felt his skinny legs wrap around my waist as my hands worked to squeeze his buns through his panty, and then he started to kiss me hungrily and run his hands all over my chest.

His tiny boner was poking me in the stomach, and it was obvious that he was grinding himself against me in an effort to stimulate it. His fingers were running through the Amazon forest of hair that coats my torso. Then he found my man’s nipples and used the palms of his hands to rub them in a clumsy but still passionate show of desire.

He broke our kiss and smiled at me, then he said, “That feels really good, Grant.”

“Oh yeah?” I said. Then I leaned in and kissed his lips softly. “Your little boner seems to have found a nice place to rub against, too.”

“It feels nice right now,” he admitted.

I used my hands to grab his ass cheeks and press his crotch harder into my gut, bringing out another moan from the horny youngster. He looked up at me with a contemplative smile, then he rested his head on my shoulder and humped into my body with gentle thrusts.

“What’s on your mind?” I asked, easing the force of my squeezing.

“I don’t know how to say it,” he said quietly, and then he continued. I just feel great tonight. My body feels like it never has before.”

“Do you think it’s because of all the things we’re doing that are so sexy?” I asked, and he shrugged.

“I just have this feeling that I’ve never had,” he said, and then I felt his legs tighten around my waist. “You make me feel like I don’t have to be ashamed of anything, no matter what it is. I’m always feeling ashamed. Whether it’s my tiny dick or having these gay feelings or wanting to wear girlie things.”

“I’m glad I made you feel that way,” I said, placing a gentle kiss on top of his head. “I don’t want you to think that you ever have to be ashamed when you’re with me.”

“I wish it were that way everywhere,” he lamented, and my heart broke for the sissy all over again.

I slowly took my hands away from his plump rear end and wrapped my arms around his warm body, wanting to hold him more than anything.

He responded by purring softly, then he sighed, “Thank you, Grant. I know we just met, but you really make me feel special.”

“You are special,” I said, feeling a growing affection in my heart for the needy sissy in my arms.

We stayed that way for a couple of minutes, and then I felt his boner pressing against my stomach again. At the same time, I felt his head rise off my shoulder, so I released the tight hug I was holding him in and looked into his eyes. He had a naughty smile on his face, and then he looked down at the tiny boner that was trapped in his panties, pressed between our bodies, and licked his lips.

“What would you like to do?” I asked him, and he bit his lower lip.

“Can you play with it again after we eat?” he asked, and I chuckled with a nod. He smiled cheekily up at me and placed a quick kiss on my lips, then with a husky voice, he told me, “I saw a video one time where two guys were doing it in the kitchen, and the guy that was taking it up the butt was sitting just like me.”

With that, he tightened his legs around my waist and locked his hands together behind my neck, and then he went on. “The one that was doing him picked him up off the counter and kept his big cock up the guy’s butt, and they were kissing the whole time. The guy kept fucking him while they were walking all the way to the bed.”

Before I could reply, he leaned in, and we shared another tongue-filled kiss while his legs tightened even more around my waist. He was lifting his ass off of the counter, so I took the initiative and let my hands travel back down to his buns. With two handfuls of hot, fleshy sissy butt, I started to squeeze and massage his rump while my pinkies slipped into both of the leg openings of his briefs and found his crack. He moaned hotly into my mouth when he felt my probing digits invading his crack. Then he panted hard and ground his tiny boner forcefully into my stomach.

“Do you like that, Ricky?” I asked him passionately, and he nodded his reply. “Would you like to be the one who gets cock up the butt and walks all the way to the bed?”

“Yes,” he hissed, then he planted a series of wet kisses all over my shoulder and my neck. “Grant?”

“Yes?” I said softly, letting my two pinkies worm their way into his crevice, where the heat of his sissy pussy was nearly overwhelming.

“I really want you to make love to me tonight,” he said, still grinding his little boner into my body, then he confessed his sudden need to me. “Instead of playing with my dick after we eat, I want you to make my butt hole feel good with your tongue like you did last time.”

“You really enjoyed that, didn’t you?” I observed, and he nodded almost frantically into my neck.

“I hope that when you make love to me, it feels as good as it did when you licked my butthole out on the couch,” he expressed.

“I promise to make it feel special for you,” I told him in a soft voice. “I’ll make sure that when we’re done, all of your dreams will have come true, OK?”

“OK,” he said with a dreamy sigh, then he lifted his head from my shoulder and looked deep into my eyes with the sweetest smile I’d ever seen.

My heart was racing as I took stock of the sissy who was asking me for anal sex, and as I held onto his bubble butt with a tight grip, I felt more heat pour out of his sissy pussy. As if he knew what was running through my mind, he leaned in and planted a sweet kiss on my lips, then he looked down at his boyhood, which was still raging in his panties, and smiled.

Just then, the timer to the oven went off, and he dutifully untangled his legs from around my waist. At the same time, I pulled my pinkies out of the leg openings of his panties. I washed my hands at the sink, then I donned an oven mitt and took our food out so it could cool on the stovetop. He was watching me with a quiet smile the whole time, and while I wondered what was going through his mind, I didn’t ask him. Instead, I let the sissy study me from his spot on the kitchen counter. At the same time, I pulled the oven mitt off and then approached him, running my fingers through his hair while an affectionate smile spread across my own face.

“I think we have time for one more kiss while our food cools,” I offered, and he nodded with a smile that lit up his face as I leaned in and pressed my lips to his.

He accepted my kiss with a flutter of his eyes, and then he wrapped his arms around my neck, letting them hang off his shoulders while we shared a deep kiss. In the middle of our tongue session, he once again wrapped his legs around my midsection, and I felt his little stiffy poke me in the stomach, then he moaned softly. Knowing that he was feeling completely uninhibited for the first time all evening, I ran my hands all over his fleshy globes. I playfully lifted his butt off of the counter, bringing out an even more passionate moan from the sissy as our kiss intensified.

When it was over, he smiled lovingly into my eyes and sighed as I let his bottom rest back down on the counter. His arms were still resting around my neck, and he was clearly in want of more romance. Still, I knew that if we were ever going to make it up to my room, we’d have to move things along by getting some food into his growling tummy. So, with a wet kiss on the lips, I extracted myself from his embrace and took two paper plates down, then I dished up our food and carried it to the table.

As soon as we sat down, Ricky showed me that, indeed, he was a hungry teenager. He quickly picked up his Hot Pocket and systematically devoured it before I could get through half of mine. Ricky proceeded to decimate the tater tots on his plate. When his food was gone, he picked up his glass of soda and downed it quickly while I watched with amusement. Fearing that I hadn’t cooked enough food for the growing youngster, I offered him my tater tots, but he declined them sheepishly.

After we ate, I let the sissy sit at the table and let his food process while I carried our empty paper plates back to the kitchen. I heard him let go of a loud belch, and as I smiled over my shoulder at him, he gave me an embarrassed grin and covered his mouth with both hands. I winked at him again, and then I continued with the task of cleaning up behind our mini feast, smiling to myself.

At 18 years old, Ricky still possessed many boyish qualities, and the loud belch he released after a satisfying meal was just one example of that. The fact that he looked so natural and relaxed in his white briefs was another stark example that he hadn’t yet emerged from boyhood. In fact, if I hadn’t seen what appeared to be a brand-new Honda Civic fitted with custom rims sitting in front of my house when I opened the door to let him in, I might not have believed that he was of age.

But if his sexual needs had a voice of their own, they would practically scream horny teenager at the top of their lungs. His adorable humping of my stomach with his hard little dick was a sure sign that he was completely inexperienced and that he had come to learn at my college of sexual awakening. And yet he still had so many needs, needs that should have been met at home but, for whatever reason, were neglected by his parents.

His desire to cuddle and be held when we were sitting on the couch could have been construed as a purely romantic overture by the sissy. But then he lamented to me that he didn’t get to cuddle with his parents after a certain age, and I realized that I was filling a need that the sissy had for intimate physical contact.

These thoughts were running through my mind, almost in a flurry, when I felt the sissy walk up from behind and wrap his skinny arms around my body. His chest and tummy felt so warm, and when I felt the soft skin of his cheek press up against my shoulder blade, I felt a shudder run through my loins.

“Hey,” I said softly, reaching over my right shoulder to run my fingers through his hair.

“Hey,” he said quietly, and then he began to rub his cheek against mine.

“What’s on your mind, Ricky?” I asked, and he let go of a soft moan.

“I was kind of hoping we could have some more fun, Grant,” he said. Then he released his hold, and I turned to face him.

He was smiling up at me, hopefully, and I couldn’t help myself. I planted a kiss on his lips, then one on each of his cheeks, before moving to his neck, where I left a trail of kisses all the way down to his torso.

When I got past his left nipple, I knelt and continued to string together a long row of kisses that took me right down to his package, which was bulging in his panties. I gazed up at him, watching him look down at me with a horny smile. Then, I used my fingertips to hook the waistband of his panties and unwrap his package once more.

When it sprang free, I leaned in and planted a kiss right on the head, and then I used my tongue to trace all around the crown. I felt his dick jump, so I looked back up at him and gave him a wink. Then I let my tongue take another pass along the head of his little dick while he shuddered. After taking the time to appreciate the ridge around his glans, I kissed all the way down the length of his boyhood until I had my pursed lips up against his warm, hairless nut sack.

I drew in through my nose, inhaling the scent of pure sissy and letting it wash over my senses. I took special care to let my mouth envelop his ball sack and use my tongue to bathe it all over. I heard him moan, so I let my gaze drift back up to his face, noting to myself that he seemed to be steadying himself as waves of goodness washed over him.

When I let his ball sack go, I gently wrapped my lips around the head of his dick and gave it a long, sensual kiss while his toes curled by my knees. Wanting to show him what a good blow job could feel like, I drew upon my many years of experience. I swallowed his teen babydick whole, taking it to the back of my talented throat with ease and making sweet love to it. I could hear him panting in response, so I used my tongue to bathe the underside of his dicklette while I sucked on it with lust-filled moans. When I thought he might cum, I pulled off of his dick with a slurp, then I used my tongue to lap up every inch of drool I could find before smiling up at him.

“That felt so incredible, Grant,” he said in a boyish tone, his eyes once again filled with wonder.

“I’m glad you enjoyed that,” I said, then I grabbed his hips and made eye contact with him. “Why don’t you turn around and put your hands on the counter so I can service your sissy pussy while I’m down here?”

“OK,” he agreed quickly, and then he allowed me to steer his hips so that he was facing away from me.

I watched him place his hands on the counter, just as I instructed him to do, and then he hung his rear end out for me. With a jolt of electricity that ran through my loins, I parted his cheeks and took the site of the beautiful sissy pussy that I was so hot to feast on. It was still moist with ass juice and bright red from my probing fingers, as well as my earlier feast on the couch. The pheromones that were rolling off of it were so powerful, making me dizzy with lust as my hard cock strained painfully in my boxers.

Feeling incredibly turned on by the delicious-looking sissy pussy that I was drooling over, I had an incredible urge to dig in right away. Somehow, I managed to contain myself as I leaned in and planted a long, wet kiss right on the puckered hole, and then I used my tongue to probe all around it.

Right away, Ricky gave off a long, horny moan that told me he was enjoying my feast as much as I was, so I centered the tip of my tongue between the lips of his entrance and started to lick it back and forth. The savory taste of Ricky’s sissy pussy was so intoxicating, and as his moans increased in volume, so did his flow of ass juice.

I felt the horny sissy push back with his hips, so I grabbed onto them with both hands and pulled his rear end into my face, wanting him to know that it was OK. As he ground his rear end into my probing mouth, I began to eat him deeply, eager to lap up as much ass juice as I could. I pulled off for a moment, giving myself just long enough to rub his puckered entrance with three fingertips so that I could stir up his pheromones again.

Then, I dove back in for more. Ricky’s whole body seemed to tense up, and he was hanging onto the counter for dear life. At the same time, I pushed up into his rear end with all of the force I could muster, eager to bring him as much pleasure as I could while, at the same time, hungry to devour as much of his ass as I could.

I could hear the pace of his pants get quicker, alerting me to the boys’ impending climax, so once again, I ended the oral pleasure for the youngster by pulling my tongue away.

When I stood up, Ricky spun around and wrapped his arms tightly around my torso, resting his head on my chest and hugging me tightly while he took deep breaths. I immediately wrapped my arms around the sexed-up teenager. I held him close, listening as he whimpered in my embrace.

“Are you alright?” I asked, and he nodded feverishly without letting go of my body. “What’s going on?”

“I don’t know, Grant,” he admitted in a whisper, then looked up at me with the most needy expression I’d ever seen. “You made my butt feel so good just now. I never knew that I could love it that much.”

“I just wanted to make you feel good back there,” I said softly, and he sighed into my chest.

“I feel really hot for it right now,” he admitted to me, then he went on. “The whole time you were licking me out, I was pretending that you were giving it to me in the ass with your dick.”

“You’re really horny for that, aren’t you pal?”

He nodded up at me, then he puckered his lips and beckoned me to indulge him. With a warm smile, I leaned in and planted a long, tongue-filled kiss on the sissy’s mouth while I ran my hands all over his back again. When I placed my hands on his bare buns, he moaned hotly and placed his arms around my neck, and then I felt him tugging on it.

As if I were reading the youngster’s mind, I knew what he wanted me to do next, so I took a firm hold of his fleshy mounds and lifted him so that I was supporting his weight in my hands. I set him back down on the counter so that he could wrap his legs around my body. He smiled through our passionate kiss, then sighed into my mouth, and our lips parted.

“Are you ready to go upstairs?” I asked tenderly, and with a sweet smile and eyes filled with need, he nodded his answer.

“Will you kiss me and take me upstairs, Grant?” he asked me shyly, and then he rested his head on my shoulder, tightening the grip of his legs.

“Of course I will,” I said in a near whisper as I used my manly hands to grip his buns as tightly as I could and lift him off of the counter.

He lifted his head from my shoulder, and we fell into a deep kiss. For a moment, I just held him in my arms. At the same time, I stood still in the kitchen, basking in the heat that our bodies generated as they rubbed together while we shared a long, passionate kiss. Finally, feeling an ache in my balls that told me it was time to seed his virginal sissy pussy, I turned and carried my lover up the staircase to my room.

By all accounts, Ricky was prepared for intercourse with me. I had taken special care to prepare him properly, first by orally servicing his sissy pussy, then by digitally servicing it. While my probing fingers were working their magic in the hot, tight confines of the sissy’s love tunnel, they were simultaneously applying enough lube to make this as painless an experience as possible. While I was lubing his sissy pussy, we shared a multitude of long, tongue-filled kisses, and I made sure that I spoke to him in gentle tones.

Still, I wanted this to be perfect for him, so I took extra care to tend to Ricky’s emotional needs as I prepared to deflower him in my bed.

“How does your sissy pussy feel?” I asked as I raised his legs and placed the head of my cock against his impossibly tight hole.

I was leaking so much pre-cum that I knew I could add to the lubrication that the sissy had in his bottom, so I carefully painted the outside of his hole with the drool of pre-cum that was seeping out, then I settled the tip against his love tunnel. As soon as I felt my glans against his puckered entrance, the heat of his treasure wrapped itself around the head of my cock, and I struggled to maintain my composure.

“It feels really good, Grant,” he practically sang, looking up at me with starry eyes.

I leaned down and planted a sweet kiss on his lips, then continued speaking to him. “You know, this is a really special moment for both of us,” I told him, and he nodded in agreement as I began to apply just the slightest pressure against his star. “It means so much to me that we’re sharing this moment.”

“It means a lot to me too, Grant,” he sighed, then he reached up and ran his fingers through my hair. “I can feel your cock down there, and I can’t wait to feel it inside of me.”

“I can’t wait either,” I assured him, adding another level of pressure against his hot, lubed-up asshole. “You’re such a sexy girl. Did you know that?”

He shook his head no with a dreamy smile on his face, so I leaned in and kissed him again. Then I added some tongue, and his asshole started to bloom. As if he could feel it happening, he wrapped his arms around my neck and engaged me for a full minute while I let things happen naturally at his back door. As his asshole started to open up, his moist glands started to encase the tip of my dickhead, just past my piss slit, so I took the initiative and added just a tad bit more pressure.

The result was a long, heated moan from the sissy and another couple of centimeters of entry for me. The heat that was encasing the head of my cock was unreal, and I realized that I had never been with a sissy this inexperienced before. When we broke our kiss, he looked up at me with eyes that seemed to be pleading.

“Am I doing a good job?” he asked softly, and I nodded my assurance.

“You’re doing a great job,” I promised him. “You have such a tight sissy pussy, and it feels really nice around my cock.”

“I can feel it getting deeper,” he observed with wonderment, and I nodded in agreement. “It feels nice, Grant.”

“That’s how it’s supposed to feel, Ricky,” I said, then I felt the head of my cock sink in a little more as pre-cum ran out the end and trickled into his tight confines.

I watched his expression carefully for any sign of discomfort, but I didn’t see one. Instead, the horny youngster’s expression gave away his determination, and with a slight grunt, I felt him try to make his asshole bloom again so that he could take more of me.

“Not yet,” I cautioned him. “Just take it easy and let things happen, OK? I don’t want you to feel any pain.”

He nodded his agreement, so I leaned down and kissed him again as the head of my cock sank a little deeper into his well-lubed love tunnel. I saw him shift a little beneath me and worried that he might be feeling some pain, but when I inquired, he shook his head no and told me, “I feel like I can take all of it right now, Grant.”

“How about if you just let me get the head in, and we’ll see how you feel after that?” I offered, and he accepted my overture.

Knowing that this was going to be the hardest part, I gave a slow and careful push. I felt my glans melt into Ricky’s impossibly tight sissy pussy. I saw him bite down on his fist, and he panted hard for a moment, and I contemplated pulling out right away. But just as this thought crossed my mind, he strained below me, and the head of my cock slipped past his anal ring.

As soon as he had it inside him, he took his fist out of his mouth and panted through a contented smile, then let out a deep breath. At the same time, I felt an incredible throb of horniness course through my body as both the realization of what was happening and the soaring feeling of pleasure hit me at the same time. Seeing my little lover in so much discomfort, though, I felt compelled to put him first.

“Does it hurt?” I asked, and he shook his head no.

“It only hurt for a second,” he told me, his eyes filled with love. “Now it feels nice again.”

“Are you sure?” I asked, and with a smile, he nodded up at me.

“Your cock feels like it’s cumming already,” he said with a naughty smile.

“It’s just pre-cum,” I assured him. “You’ll know how it feels when I cum, and I hope that you’ll enjoy it.”

“I’m going to,” he told me. “I love feeling your big cock in me, so I know that I’m going to love it when you cum inside of me.”

“You’re such a sexy girl, Ricky,” I told him. Then I leaned in for yet another kiss, adding a little more length.

He moaned into my mouth, and then he reached up, wrapped his arms around my neck, and kissed me hungrily. When we broke our kiss again, he smiled up at me and sighed, “I really like you, Grant.”

“I really like you too,” I said. “Are you comfy?”

He nodded his answer with a soft moan, so I carefully added a little bit more length. As I pushed in, I could feel the hot, moist lining of his sissy pussy envelop a new section of my shaft, causing me to have to compose myself as the urge to begin fucking the sissy almost took me over. Instead, I steadied myself and smiled lovingly at him, knowing that he was placing all of his trust in me.

“Is that alright?” I whispered, and he nodded again. “Let’s rest for a little while, then I’ll add some more.”

“Alright,” he said in a sweet voice, still gazing up at me with stars in his eyes. “Grant?”

“Yeah?”

“Does it feel this nice every time?” he asked, and I nodded down at him.

“It will feel this nice every time that you and I are together,” I promised him, and he sighed again.

“If we become boyfriends, can we do it every time?” he asked, and I nodded again.

“Are you ready for more?”

“Yes,” he hissed, so I gently placed my lips to his and added enough length so that I was buried halfway inside of him. Then I stopped and let him rest again. He looked deep into my eyes with an expression of pure affection, then he told me, “Your cock feels really hot, Grant. I love it.”

“Your sissy pussy feels nice and hot, too,” I said. “How about if we share another kiss, then I’ll give you some more, OK?”

“I’d like that,” he whispered, then he puckered up, and I planted a long, wet French kiss on his mouth while he moaned hotly and held onto my neck.

While we were lost in the pleasures of our kiss, I carefully slid a little deeper into the sissy, causing him to moan even louder as a grin of lust formed on his face. Instead of breaking our kiss, I maintained it and tested the waters by adding just a little more. With another hot moan, he accepted my offer. When we broke our kiss, I looked down between us and saw that my wild patch of pubic hair was now touching his and that I had about two more inches to go until I was all the way inside of him.

“We’re almost there,” I said with a smile, prompting the horny youngster to smile back.

“It feels really good, Grant,” he told me. “I can’t wait until you’re all the way in me.”

“I can’t wait, either,” I assured him. “This is such a special time for us both, isn’t it?”

“Yeah, it is,” he concurred with a grin, so I leaned in and planted a sweet kiss on his moist lips.

“Grant?”

“Yes?”

“After we make love, can I suck your cock?”

“Is that what you want?” I asked, and he nodded. “Then, of course, you can.”

“Sometimes I think about sucking cocks,” he said with a naughty grin, his earlier inhibitions now a thing of the past. “It makes me feel really horny.”

“Were you thinking about sucking cocks when you came over here?” I asked with a lecherous smile.

He wagged his cute eyebrows at me and licked his lips. Then, he changed the topic. “Put it the rest of the way in,” he instructed me, and with an amused smile, I nodded obediently.

Not wanting my little dick lover to feel anything but pleasure, I leaned in and engaged him in another deep French kiss as I carefully sank my shaft the rest of the way into his hot, tight sissy pussy. I felt my pubic bone smash up against his taint and his hairless ball sack, and I knew that I was all the way inside of him. We broke our kiss and shared a loving smile that lingered for a long moment, a moment where we both remained silent and soaked in the enormity of what was happening.

He bit his lower lip and batted his eyes, then reached out to caress my cheek with a grateful smile as I tried to process what was happening in my heart. I could hardly believe that this sissy was in my bed, allowing me to take his virginity, and yet it was happening. And he was so sweet and so innocent, yet he all but commanded me to sink my shaft all the way inside of him so that his deflowering would be a fait accompli. Unable to deny the lust in my body, I leaned back in and kissed him deeply while I stirred my hard rod in his tight confines. Then, I broke our kiss and took command of the situation.

“Are you ready for me to make love to you?” I asked gently, and he nodded up at me with a submissive moan.

“This is what I’ve been dreaming about, Grant,” he told me with a beautiful smile, then added, “and this is what I’ve been moaning about.”

“I want you to tell me if you want me to stop, OK?” I asked, and he gave me a needy look.

“I don’t want you to stop,” he practically pleaded, so I reached down and brushed his bangs away from his eyes.

“No, I’m not going to stop unless you ask me to,” I assured him, and he smiled contentedly. “But if it hurts, I want you to tell me, OK? This is supposed to be special for both of us.”

“It’s really special for me,” he declared in a near-feminine tone as if he were out of control of his speech. “I just want you to make love to me, Grant.”

“OK,” I said gently. “Give me a nice long kiss, and we’ll start making love.”

With that, the starry-eyed teen wrapped his skinny arms back around my neck and pulled my head down until our lips met. Then his tongue slipped into my mouth, and he moaned submissively again. Knowing how much this meant to him, I took control of our kiss and pulled back gently, just taking about two inches out of the sissy’s tight rear end, then I slowly eased back in.

He sighed into my mouth when he felt my first thrust, so I pulled back a little further, this time taking about three inches out. I slowly slid it back in, feeling the hot lining of his sissy pussy sizzle as I did. I pulled back a third time, this time easing out about four inches. I slowly slid it back up his chute, and once again, the sissy’s pleasure receptors sent a shiver through his young body.

Knowing that he was in the midst of a dreamy first lay, I settled into a gentle, in-and-out motion. I momentarily forgot about my pleasure and focused on young Ricky’s needs, wanting to make this a night that he would never regret. With each in and out stroke, I would withdraw four inches of hard cock, then slide it back in while the sissy moaned with passion into my mouth.

I could feel the head of my shaft dragging along the lining of his sissy pussy, catching every nerve ending along the way, then pushing back in and hitting his prostate just right. His young love tunnel was juicing heavily around my dick, and I could see the passion burning in his eyes as he took inch after inch of hard dick with every inward thrust that I gave him.

His young dicklette was starting to dance around on its own, a sure sign that an anal orgasm was near. Knowing what was happening in his young body, I increased the force of my inward thrusting just enough to scratch the deep itch that he was feeling. It was an itch that originated at the core of his sissy pussy, an itch that he had been feeling for years. And finally, he was getting that itch scratched with the only instrument that was long enough, hard enough, and with the right contours to bring him the satisfaction that he craved.

I could feel his smooth nut sack start to pull tight as I drove in harder and harder, and then I felt his fingertips digging into the back of my neck as his left leg started to twitch on its own. I kissed him harder and fucked him even deeper. I felt his sissy pussy start to throb almost uncontrollably around my shaft as I continued to drive into it with long strokes of the hard, horny manly cock.

Soon, the powerful throbbing in his hot sissy pussy became rhythmic, just like my thrusts, and his eyes glazed over while his entire body shuddered. I felt his young body start to spasm just as his tight rectum started to squeeze the length of my shaft like a boa constrictor, sending a powerful heat through my groin that told me that my orgasm wasn’t far off.

Before I could consider the intense pleasure that I was feeling. However, Ricky gave off an animalistic howl. His entire body seized up, then his young cock throbbed in time with his sissy pussy, and he fired off four thick ropes of sissy jizz that hit him in the chin, then on the neck, and across the chest. The rest of it shot out and landed on his tummy, right below the navel. Then it started to pour out of the end of his untouched dicklette while he writhed in pleasure beneath me, his head turning from side to side the entire time.

With Ricky’s first anal orgasm now behind me, I knew that I could take a little for myself. But I was still determined to please the sissy in my bed, so I continued to drive in with deep thrusts as if his climax hadn’t happened yet. This caused his burning sissy pussy to clamp down with even more force over and over again, and I knew that my end was nigh. So in a moment of sheer devotion, I leaned in and kissed the sissy as deeply as I could while my climax played out.

With my tongue dancing so romantically with his, I felt my cock erupt with spewing man cum, and I seeded his sissy pussy while he moaned beneath me. As my cock delivered shot after creamy shot of my sperm, I continued to thrust in and out of his sissy asshole with caring, considerate strokes until finally, I buried my length all the way inside of him and finished.

When my cock stopped pouring cum into his love tunnel, Ricky and I shared a loving smile, and I stayed where I was, resting deep inside his treasure while we caught our breath. I pressed my lips to his one more time, this time giving him a sweet kiss with no tongue, and then I brushed his sweaty bangs out of his forehead and spoke to him.

“How was it?” I asked, and he sighed dreamily.

“It was incredible, Grant,” he declared. “I don’t know how to say how I feel right now.”

“You don’t have to say anything,” I assured him. “As long as you’re satisfied, I’m happy.”

“I’m really satisfied,” he told me in a gentle voice. “You made love to me better than I ever dreamed.”

With that, I planted another kiss on his lips, then I carefully eased my dick out of his sissy pussy while he bit his lower lip and watched. As soon as I was out, I eased my body down so that I was face to face-with his winking rosebud. I lovingly cleaned it with my tongue, wanting to make sure that I thoroughly serviced it for him. He was moaning softly and exclaiming his pleasure through his urgent panting, so I took my time, eager to please. When I stopped eating at his back door, I approached his side, and Ricky immediately melted into my arms.

“Grant?” he whispered as I ran my hands up and down his back.

“Yes?”

“Can I tell you something, and you won’t get mad at me or think I’m lame?”

“Of course.”

“I love you right now,” he confessed, and my heart melted.

“I love you right now, too, Ricky,” I conceded.

With that, he smiled up at me, and we shared a brief kiss, then he settled back into my embrace. As I considered what he and I just said to each other, I felt him snuggle up to me as tight as he could. Wanting to make the sissy feel as safe and as loved as I could, I held him close while he fell into yet another deep slumber, this one the product of his first-ever intercourse with a man.

The End.

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