tagTransgender & CrossdressersWeekend of Love Pt. 01

Weekend of Love Pt. 01


"Calm down," I told Leland as I slowly sucked him off. I had scheduled our first bed and breakfast getaway this weekend, but for some reason he was very anxious about it.

When he came in Friday evening, I kissed him excitedly, but he pulled away. "I'm just afraid of being judged. Can't we just stay here?" So I put my arms around him tightly, and did what I thought would help cool off the pressure.

I dropped to my knees, fished out his cock, and wrapped my mouth around it without ceremony. He moaned, ran a finger through my hair, and I knew we were ok. "So," I asked between sucks, "what are you really afraid of?"

"It's the mingling with the other couples," he confessed, jerking now, "I can't stand their eyes on me, all the ridiculous smalltalk." I reached behind to squeeze his ass, pulled him in deeper, and let him finish spasming, then lifted off with a long suck.

Standing up, I kissed him deeply, returning his cum. "Look, it's simple. You don't have to spend time with anyone else. Really. We'll leave tonight and get in when no one's around."

This perked him up, and I kissed him again. "But I did want to spend the night with Lolita, so get going!" He smiled and turned around, and I went to finish off some work before I finished packing.

I heard the shower turn off, and tiptoed to the bedroom. I loved watching Lolita coming into being, and today was no exception. As she wrapped a towel around her, sat down at the vanity and opened her purse, I pressed against the door, catching glimpses of her reflection being transformed.

I felt a surge of happiness bubbling through me. The world was a better place for Lolita in it. I was happy she could live the way she wanted, I was happy I could make a space for her, and I was also happy that I got to, er, enjoy some of her efforts.

"You can come in, you know," she giggled, and I sank into our favorite armchair. She turned, rose, and walked towards me, my face dipping back in awe and love, at her exquisitely painted lips, eyes, cheeks, everything!

"I got something for you," I managed to get out, pointing to the new lingerie I had laid out on the bed. "I saw that," she replied, and bent down for a kiss. I unwrapped her towel and drew her on to my lap. I ran the back of my hand along her smooth skin, her long legs, her bald pubes, her puffy nipples, her dainty neck. I held her cheek and just looked at her for a while, before kissing her wildly.

"Hey," she pushed me away, "don't screw up all my work! Now lay back". I complied in protest, as she unbuttoned my shirt and trousers, slipping them off as she mouthed my cock through the cotton, leaving a red "O" ring on it. Bunching up my cock and balls, she gently kneaded them, until I got harder, and she pulled down my underwear. "I'd love to oblige," she said, "but you aren't going to come down my throat today."

She turned and bent down briefly, and pushed up her smooth globes, showing her glistening pussy. I leaned in to lick her and open her up, and smelt the cinnamon lube. Seeing how well she had prepared herself for me, I felt a wave of gratitude sweep over me, and just dug my face between her ass cheeks, slurping hungrily.

I helped her up until she turned and climbed up, sitting down slowly, lining me up as I held her face in my hands, and we both gasped as I slipped in. She rotated her hips while smiling at me, until she hit bottom, then lay down on my chest, put her arms around my neck and rested her face to the side of mine.

"Don't worry about me, I'm fine. I love that you arrange this trip for us." She kissed my cheek, "now let's get off to a good start," she whispered, "fuck me good!"

I held on to her hips and held her close, as I began moving, slowly at first, pulling out half way before going back in deep. "Oh yeah baby," she moaned, "oh deep, yeah, fuck, deep, yeah, uhmm, fuck, harder, pound me", before suddenly clamming up and biting into my shoulder.

"What's the matter?" I asked? "I'm afraid of being too loud over there," she replied, nuzzling my neck.

"Well we're here right now, ok?" I ran my fingers through her hair before gripping it, "so here's what's going to happen: I'm going to fuck you, and you're going to cum. I'm not going to hold back anything while I'm fucking you, and I don't want you to hold back anything when you cum, got it?"

I decided she was slippery enough and keeping one hand on her lower back and gripping her head with the other, began banging hard up into her. Soon the room filled with the sound of my strenuous grunting, my balls slapping against her ass, her hard dick slapping against my stomach, and her wailing.

"Fucking pound me, yeah, oh God!"

"Gghn Yeah," I encouraged her, "you like this, baby? you like me filling you up, you little bitch?"

"Yeah, give it to me, just like that! I'm you're little slut, baby, use me, use me good."

She lifted her face up, looking down at me for an instant, than her mouth twisted, and her forehead collapsed on to mine. I felt her twitch around me, as with adorable little spasms she dribbled out between us, then sighed and laid back on my shoulder.

Feeling close, I bit into her neck, "I'm gonna cum, baby, I'm gonna cum so hard!"

"Do it baby," she cooed in my ear, "fill me up, cum inside me baby, fucking breed me!"

"Urgh, huh!" I thrust madly, squeezing her ass, as her hands moved to my face and chest, reassuring me, and loosened her ass a bit as I tensed and unloaded, shouting with each push, feeling her channel get slippery.

She moaned in response, turning her eyes upwards, and a small shudder passed through her. After the initial squeeze around my cock, I felt her relaxing once more, letting me massage her inner walls.

"Gonna push it a bit deeper into your pussy, honey," I said, pulling her cheeks apart as best I could and moving long and hard, "and I want you to keep it there for me." She giggled, and nodded, and when I was soft and about to pop out, placed both her hands under herself and slowly climbed off, then, hands covering her hole, bent down.

I reached for the plug I had left on the table (a recent "ace of spades" model we had started using), then slathered my hand in her cum on my chest and rubbed it all around it, and slowly slid it into her.

She stood back up and hugged me. "I feel we were a bit rushed today," I told her, "but I promise tomorrow is going to be a long, slow day of loving!" She left to wash up and fix her makeup, then returned to wear the sheathed panties which I had bought her along with a blue floral dress that looked great on her.

"Do I need to pack anything else?"

"Well," I replied, "you pack the clothes, I'll pack the toys."

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