Soft-mouthed Sandy Pt. 04

Betty smiled. "Racking up the notches on your bedpost, huh?"

I rubbed my neck. "I've been a pretty good boy here at school so far. Focusing on my classes, writing for the school newspaper and magazine. I even organized a few campaigns for student government."

"But," she said.

"I hadn't really been tearing it up in the dating department until extremely recently."

She leaned into me a bit. "And now you're hooked on experimenting?"

I nodded. "Is that an alright attitude to take?"

"Well, I hope you have not been leading a double life, pretending to be wicked and being secretly good." She said, in a more than passable British accent. "I wish the world in general were ready for a little more experimenting, Sean. But that might be wishful thinking on the part of a typical 18-year-old Trans girl."

"Someone with your brand of smile and sense of style who quotes Oscar Wilde? What is that song Masterson sings in Guys and Dolls?"

"You mean," She cleared her throat. "Luck be a lady, tonight. Luck if you've ever been a lady to begin with. Luck be a lady, Tonight. What about it?"

I nodded. "Just you never know what's happen with any roll of the dice," I said. "And, you're right,, you sing better than Brando in the movie."

She smirked. "Well, thank you kind sir."

We finished our walk and I offered Betty a ride back to the Apartment complex in my truck. "Save you a couple steep hills," I said.

She accepted and I drove her off campus and parked in front of my apartment less than 8 minutes later.

"Want to come up?" She asked, after I'd shut off the engine. "Fi is out shopping for a dress. She gave me a key."

I checked my watch. It was just past 11:00. I had two hours to kill before Sandy was expecting me. And my date with Fiona was not until the afternoon.

"I could pop up for a bit," I said.

"Shoot the breeze," she said, finishing her iced coffee, smiling at me slyly.

We walked the flight of stairs up to Fiona and Betty's apartment. She produced a key from her pocket and we entered.

I had never made the trip up the stairs to Fiona's. But it's layout was similar to mine with the exception of having a second bedroom and a balcony off the master bedroom.

Betty tossed her key and her clutch on the counter and walked to a low-slung modern style chair, to fold her foot underneath her and twirl once in the chair. "I can't wait to move in here!"

I noted that the larger bedroom was in the process of being packed neatly into boxes. "And you get to be Juliet on her balcony, eh?"

"Fi didn't feel like moving her stuff. I did have to promise to let her paint on the balcony when the weather is nice, but," she rose from the chair, shrugging, putting her hands in the pockets of her hip hugging skater shorts. "I'm not planning on being very difficult to live with."

I held up my empty iced coffee cup and offered to take hers to the trash.

"It's under the sink," Betty said.

I opened the cupboard and ditched the cups in the bin. When I turned, Betty had peeled off her halter top revealing a small white brassiere.

She tossed the halter aside and crooked her finger at me. I moved towards her, my hands going to her slender hips.

"I'm hoping to get them augmented," she said. "You can only grow so big with hormone treatments," she said.

I nodded. "I think you're very attractive," I said, waiting for her to initiate things. She seemed to hesitate a moment, then giggle.

"I'm sorry this is my first time actually kissing a boy that wasn't in a play."

"Never been kissed?" I asked.

"I didn't even get asked to prom."

"What a pity," I said, leaning in slowly. "And your lips look just so kissable."

She leaned into the kiss and I felt my hands move up from her hips to her back, our pelvis coming naturally together. Her tongue darted against my lips and I opened for it, accepting it as she pushed into me with soulful abandon.

We eventually came up for air and I blinked at her brilliant blue eyes. "Better than a stage kiss?" I asked.

Her hand moved to my belt. She fingered the buckle coyly. "So good I'm tempted to go a few steps further," she said. "Promise to be gentle with me?"

I swayed with her and kissed her again. "My middle name could be gentle," I said.

She stepped back, removing her bra entirely. She undid the fly on her hip-huggers and peeled them down revealing a pair of lacy panties. Nestled within was a discernable bulge.

She stepped out of the jeans and walked back towards me unbuttoning my shirt. "You okay, so far?" She smirked.

I was fine. Her kisses continued as she undid the buttons on my shirt, kissing down my neck and chest. She wrestled my shirt tails out of my jeans and undid my belt.

I shrugged out of my shirt and tossed it atop her halter, jeans, and bra. She pulled the belt out of my belt loops and brought it up over my head using it to pull me back into a kiss.

I cupped her close squeezing her ass gently.

"The chair?" She asked, pointing with her chin. "My bed doesn't arrive until Fi's old roomie moves out."

"Wherever you like," I said.

She laughed, leading me with the belt. "I might have to have all my lovers on leashes one day."

She bent forward over the chair and I began pulling down her lace panties.

She maintained her hold on the leash with her right hand while her left went down to cover her semi-erect member. It was shaved and her arousal was a bit difficult to cover up with just one hand.

I unzipped my own jeans and, spitting in the palm of my hand, I lubed up the tip of my own hard-on.

"Slow down, there," she said, going over to her backpack and digging out a condom and a slender bottle of clear lube from a side pocket. "Be prepared, right?"

I let her slip the latex coat over my shaft and then she squeezed a healthy dollopof the lube on the tip. She smiled. "More fun than the banana in 10th grade health class."

I pulled her up and kissed the side of her neck. She turned back to resume her position, bending over the chair. I pressed the head of my cock against her little pucker. It was tight and unyielding at first but she moaned to feel my girth knocking on her back door.

I drew my cock back and she took hold of my fingers, sucking on and thoroughly wetting my index finder up to my second knuckle.

She released me from her lips and I brought the finger down no trace around the rim of her virginal asshole. It seemed to tighted and then, as I put my fingertip against the hole, it relented a few millimeters. She gasped as I slipped the finger to the first knuckle, working it slowly and gently. After a moment, I checked with her. She nodded asking for more of the digit.

I pressed deeper into her and she gasped softly. I felt her own hand moving, stroking along her rapidly stiffening lady cock.

"Oooh," she moaned. "Ah, thank you for being patient with me."

I smiled. "May I... stroke you?"

She was obviously self-conscious, but her hand moved from her sex organ and I used my free hand to manipulate her little cock as I kept massaging her pucker.

The more aroused she grew, the more her asshole loosed until at last I put the tip of my cock just below my inserted finger and pressed in as my finger slipped out.

"Ah, yes, baby," she shuddered, as the head of my sheathed cock slid gently inside her.

Her ladycock had achieved a full erection and as I run my thumb over the head, I felt it jump gently, a hot little stream of precum coating my fingers.

"You doing alright, kid?" I asked.

"What does it feel like?" She responded with a breathy laugh. "Just give me more. Slowly. But more!"

I pressed a bit more of my erection into her tight little opening, still running my fingers up and down her shaft, rubbing her precum into the veiny flesh like coco-butter.

She had released her hold on my "leash" and tossed my belt atop our pile of discarded clothes. Her hands went up to cup her cute little tits. She tweaked one of her pert brown nipples.

As slowly as I could, I fed my cock inches at a time into her ass, withdrawing when the muscles resisted and then after some encouragement from her, I'd re-attempt.

Eventually, I felt her pushing back against me, taking as much as she could in short strokes.

Flipping over, she lay back in the chair, bringing her legs up and presenting her asshole. I once more entered her. She moaned as I gripped her little member and it jumped in my hands as her anus tightened around my sheathed member. She shot a load of her own cum that coated her flat smooth stomach.

The sight was shockingly erotic to witness and within seconds, I too bucked, filling the inside of the condom with a soft moan of my own.

I exhaled a breath of satisfaction. She laughed looking down at the mess she'd made of herself. "I hope I didn't get any on the chair," she said. "It's the first bit of furniture I bought for the apartment."

Slipping from her asshole. I used my fingers to catch a few rivulets of her com before they had a chance to run off her body onto the fabric. She giggled at my effort but stood quickly and jaunted to the bathroom where I heard the sound of the shower.

Checking my watch, I moved to divest myself of the soiled condom. I joined Betty in the shower for just a quick moment.

"I'd stay longer," I said. "But I have a lunch meeting. I have to pick the guy up from the film school."

I moved back to redress in my clothes.

Betty appeared in a floral blouse and fresh underthings. From the floor she reclaimed her hip-hugger board shorts and her low top sneakers. "The film school, eh? I'd be curious to have a look around there. Thank I could tag along? I can board back. You'll hardly notice I'm there."

I recognized that would be extremely rude to just cum and go-especially since Betty was new in town and short on people to hang with.

"Sure," I said.

She grabbed up her skateboard and dug a clutch purse and her Ray-ban sunglasses out of her backpack. "Ready when you are," she said.