tagTranssexuals & CrossdressersDawn's Diary Ch. 04

Dawn's Diary Ch. 04


We've exchanged email regularly, but I haven't seen Sam for more than a month. She called last night and said that she had worked her last shift at the bar. She is moving out of her apartment this morning and will be on her way. She assured me that her dildo was safely packed in her purse so that it would be readily available when she gets here. I've been saving my cum in a glass in the refrigerator. It's almost half full.

I took special care when shaving this morning and put on the red lingerie that Sam gave me that last time I saw her. Then I pulled on a pair of jeans and a light work shirt so that I can help Sam unpack her car. God, I hope none of the neighbors drop by when I am outside. The buttons on the front of my shirt are almost ready to burst under the pressure of my size D breasts and, despite the confinement of the thong panties, my hard cock is straining against the front of my jeans.

The doorbell rang at a little after 2:00 p.m. I was in the bedroom making room in the closet for Sam's clothes and hadn't heard a car in the driveway. The doorbell startled me and my first thought that it was a neighbor who had walked over for some reason. Here I was with the front of my shirt bulging because of my fake breasts and the front of my jeans bulging because of my perpetual hard on. I quietly went to the front door and peered through the peephole. It was Sam.

I flung open the door and Sam lept into my arms, her purse dropping to the ground. We embraced, holding each other tightly and exchanged deep kisses. Finally, Sam broke free, picked up her purse, and said, "Let's go inside."

I had barely closed the door when Sam wrapped her arms around my waist and backed me up against the wall. She tugged my shirt free of my pants and slid her hand down the small of my back to the waistband of my panties. I felt the pull of the narrow band of nylon between my ass cheeks as she gave my panties a small tug. Breaking our kiss, Sam smiled, "Nice."

My arms were wrapped tightly around Sam's shoulders and her mouth again met mine. As our tongues continued to flicker together, Sam's hands continued to explore my body. By now, she had freed my shirt from my jeans and I felt one hand slide up across my belly up to the outside of my bra. As Sam massaged my breast, her other hand dropped to my crotch and she started rubbing the growing bulge on the front of my jeans.

I let out a small moan as she released her grasp on my breast and unbuttoned my shirt revealing the red camisole. Sam's mouth and flickering tongue moved down to my neck. Her left hand returned to my breast while her right hand continued to caress the growing bulge in my pants. There I was standing in the hallway of my house, backed up against the wall. Sam had only been there a few minutes. We were still clothed. Her grip became more firm and the rubbing became more urgent as she continued to manhandle me. I could feel the pressure in my cock rapidly building toward eruption. "I'm going to cum," I gasped.

Sam continued to massage my crotch as the involuntary heaving of my hips against her hand became more urgent. Finally, I could hold back no longer and jets of sperm spewed from my throbbing cock soaking my panties and jeans. As the throbbing began to subside, the rubbing of Sam's hands became soft caresses. Sam whispered, "I think my little wench's pussy is wet."

I was embarrassed. The wet spot on the front of my jeans was growing. But Sam just smiled. As I regained my composure, Sam said, "Let's get my things out of the car."

"Great," I thought. Here I am wearing red lingerie, the front of my pants soaked with cum, and Sam wants me to go outside.

I re-buttoned my shirt. I hoped that, by not tucking it in, the wet spot on my jeans would be hidden if somebody saw us. Sam giggled as she reached up, unbuttoned the top button of my shirt, and headed out the door. I, of course, followed her.

We hurried to carry Sam's things in from her car. It only took a few trips. Sam said that, having graduated from college earlier in the year, she really had not had time to accumulate very much stuff. She said that she had left a few things in Robin's garage and hoped to retrieve them the next time we went to the bay area.

A neighbor from across the street spotted us and waved. For a moment, I thought he was going to come over, but he must have sensed that Sam and I didn't want to be interrupted. I was thankful of that. I don't think he was able to see my red lingerie showing above my partially unbuttoned shirt or the cum-soaked front of my jeans.

Having unloaded Sam's things from her car and given her a short tour of the house, I realized that I was getting hungry. I suggested that we clean up and go down to a local bar for a bite to eat. Sam agreed and started to remove her clothes. She kicked off her shoes and slipped out of her jeans and sweater throwing them onto the bed. Next off were the boxer shorts and tank top. Before I could remove my shirt, she was standing nude in front of me.

It was at that moment that I realized how stunningly beautiful Samantha is. Her high cheekbones accent a face not encumbered by makeup. Her pert breasts easily pass the pencil test. She is trim and athletic with muscles rippling in her legs, arms, shoulders and belly—not bodybuilder style muscles, but sexy and smooth.

Samantha giggled when she saw me staring. She gave me a quick kiss before unzipping my pants and proceeding to help me divest myself of the rest of my clothes. My cock quickly sprung back to attention as we headed for the shower. I tried to wrap my arms around her as we stood together under the warm water, but Samantha resisted, "After dinner, my little wench."

After a quick shower, we hurried to get dressed. I put on a garter belt and stockings. As I was preparing to put on a pair of thong panties, Sam said, "Stop. Bend over. I want to give you a little something so you don't forget what you are in for tonight."

There is no way I was going to forget, but quickly spread my legs and bent over, resting my hands on my knees. Sam pulled a butt plug from her purse and deftly shoved it up my ass. By now, I was conditioned to being violated in such a manner and easily accepted the penetration. As I pulled the panties on and tucked my cock into the thin fabric, I could feel the strap of my thong panties pushed against the butt plug.

Sam pulled the harness for the dildo out of her purse and put it on. She said that the rubbing of the straps against her pussy would help her remember what I was in for later. Then, she put on a pair of boxer shorts and a tank top undershirt. We both put on jeans and sweaters over our gender bending underwear and headed out the door.

We ran into a few of my friends at the bar. I introduced Samantha to them and could tell that they were impressed. As we sat together in the booth eating dinner and enjoying a few drinks, the butt plug served as a reminder of my impending fucking. A couple times, Sam leaned over and kissed me on the cheek. As she did so, she rested her hand on my thigh and discreetly hooked her finger on the strap of the garter belt hidden under my jeans. She giggled a little as she pulled her hand away and the strap snapped against my thigh. My cock responded to her flirting and strained against my panties with increasing pressure.

We finished our dinners and jumped in the car for the quick trip back to the house. As I drove, Sam rested her hand on my leg, her fingers playing with the garter strap. My cock continued to swell. By the time we got to the house, the fabric of my panties barely contained my erection and the pressure of my hard cock bulged out against the front of my jeans.

The door had barely closed behind us before our jeans and sweaters were laying on the floor. I told Sam to grab a couple of beers out of the refrigerator as I headed for the bedroom to top off my feminine attire. The bra that I selected was a size D to accommodate the breast enhancers that I had worn the last time Sam and I were together. My camisole was made of spandex and had lace trim. It stretched tightly across my breasts and hugged my belly. They complimented the panties and garter belt that I had worn to dinner.

When I emerged from the bedroom, Sam was smiling. She was holding two bottles of beer in one hand and the half glass of my cum in the other. She gave me one of the beers and said, "Be right back," as she disappeared into the bedroom.

I dropped to my knees in the middle of the living room when she emerged, her now familiar dildo poking out of her boxers. She stood in front of my eager mouth, teasing me by slapping the dildo against my cheeks, letting me get the head between my lips only to pull it away, touching it to the tip of my nose, letting me touch it with my out-stretched tongue, all the time giggling. "What an eager little cocksucking wench."

Finally, Sam let me take the dildo into my mouth. I reached up and grabbed her hips pulling her toward me until the head was almost to the back of my throat. She drew back a little when I gagged, then grabbed the back of my head and thrust her hips. The gag reflex passed and I was soon able to take more and more of the dildo in my mouth as she drove her hips forward while holding my head. I responded. My hands had slipped down to her ass and I was matching her rhythmic thrusting by pulling her deeper into me.

Sam started to gasp and moan softly. The tempo of her thrusting increased as she fucked my face with more and more urgency. With one final thrust, she drove the dildo into my mouth and pressed my head against her. I felt her slowly rotate her hips massaging the base of the dildo against her pussy and I tasted the salty cum that I had been saving filling my mouth. I couldn't swallow fast enough and some of the cum dribbled out of my mouth and down onto my camisole.

Sam dropped to her knees and wrapped her arms around me. Our mouths met and her tongue flickered out to meet mine. She pulled back. Some of my cum was smeared on her chin. I wiped it off with my fingers. She took my hand and pulled it to her mouth, licking my fingers clean. I felt her hand slid down my back and her fingers probed between the cheeks of my ass. "I think it's time to remove this," she said as she lightly tapped the base of the butt plug.

I hurried to the bathroom where I slipped out of my panties and removed the butt plug. The pressure in my ass was relieved, but my cock stiffened with the thoughts of Sam's dildo and the building anticipation that she would soon be fucking my with that wonderful rubber cock. I pulled the little negligee that Sam had given to me over my head and hurried to rejoin her.

Sam had switched off most of the lights in the house while I had been changing. Only the bedside lamp illuminated the bedroom. Sam was sitting on the bed, clad only in her boxers, the dildo jutting from the fly. She smiled as I approached, my hard cock poking from under the hem of my negligee. "Lie down on your stomach," she said.

I climbed onto the bed beside her. As she leaned over me, I shuttered in anticipation at the press of her dildo against my leg. However, she didn't immediately mount me like I had expected. Instead, I felt the flick of her tongue, first in my ear, then on the back of my neck. Her hands traced the straps of my bra through the thin fabric of my negligee, then slide down to the hem and back up to cup my breasts. She slowly slid down, letting her breasts slide over my back. She lightly bit my butt check and then started to run her tongue down the crack of my ass. I moaned and instinctively raised my hips slightly. She continued down pushing my legs apart until her tongue could reach my quivering balls.

Sam licked and sucked my balls as I squirmed and moaned. My erect cock was underneath me and the grinding of my hips was rapidly taking me toward ecstasy. I felt Sam's hands spreading my buttocks and her warm tongue pressed against my asshole, gaining slight entrance with its pressure. I felt the pressure of an orgasm building and knew that I needed her inside me. "Fuck me, Sam," I pleaded.

Sam quickly moved to take me. I lifted my ass to meet her as I felt the dildo sliding up my leg toward its target. Sam positioned the head of the dildo against my eagerly waiting asshole and drove her hips toward mine. I pushed back against her impaling myself. The massive intrusion into my rectum produced a mix of pain and pleasure. I gasp, "Oh, God. I want all of you in me."

The urgent thrusting of our hips was pounding my own cock into the bed. Sam whispered, "My little wench likes my cock, doesn't she," as she nibbled my ear.

I could only moan as I continued to meet her thrusts driving the dildo further and further into my ass. Sam sensed my impending orgasm and slid her hand down to grab my cock. I couldn't hold back any longer and cum exploded from my throbbing erection. Sam eased her pounding of my ass as the contractions in my balls slowly subsided.

We lay there on the bed spent, Sam resting on top of me, the dildo still firmly lodged in my ass. Sam released her grip on my cock and we took turns licking my cum from her fingers. She softly kissed my cheek. I tried to turn to meet her mouth with my own, but couldn't reach. She smiled and nestled her face on my shoulder, her fingers idly tracing my bra strap.

I was in heaven. Sam fulfilled all my dreams and here she was in my bed. I think I dozed a little but was awake again as Sam gently raised herself off of me pulling the dildo from my battered ass. When she emerged from the bathroom, she was nude. I quickly removed my negligee and bra as she turned out the light and crawled into bed beside me. We slept soundly that night, Sam curled up in my arms, both us completely spent, and dreaming of adventures yet to come.

Report Story

bydawn43© 1 comments/ 11940 views/ 1 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (1 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (1)

Add a

Post a public comment on this submission.

Post comment as (click to select):

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: