tagTranssexuals & CrossdressersI Feel Like a Woman Ch. 01

I Feel Like a Woman Ch. 01


"Holy fuck, Shannon! That was incredible!" I panted as I laid on my back; my chest splashed white with my own ejaculate. Shannon, my girlfriend was still kneeling between my knees. With my butt raised and supported by her thighs, she slowly but continuously pumped her strap-on in and out of my asshole.

"I'm guessing you really enjoyed being fucked in the ass." Shannon gave me a wicked grin. She leaned forward to kiss me with her generous, plump lips and smeared my cum over me with her massive jugs.

"Oh gawd! Yeah! That was so..." I was at a loss for words. My body uncontrollably jerked.

Shannon undid the strap-on leaving "her cock" inside my butt. She climbed over me. Her breasts now coated with my sticky slime. "Lick me clean!"

It wouldn't be the first time I had tasted my own. She had fed it to me numerous times: cumming in her mouth and forcing it into my mouth; jerking me off in the car as I drove then licking her hand clean; drinking out of a rubber after fucking her.

After she was satisfied I had lapped everything clean, Shannon straddled my face and made me eat her until she came.

Exhausted, we fell asleep on her bed.

We awoke Saturday morning. I relaxed in bed since I had no work to go to, but Shannon was a very successful real estate agent with some showings today and got up early to get a head start. She threw a number of things on the bed before going to the bathroom to take a shower.

Now Shannon was not a big woman other than her breasts. She was a natural beauty with dark hair, big dark eyes, a pretty face with plump, pouty lip and a curvaceous body. Her well-proportioned legs always looked great in the stockings and garters she often would wear for me. The high arches on her perfect feet never failed to get me excited.

Atop the pile of clothes was her bra. Black. Lacy. Beautiful. I picked it up and held it by the straps. The cups were huge to accommodate her bosom; at least D's. The label had been removed so I really couldn't tell you the size, but curious I held her bra against my chest.

"Well don't you look cute!" Shannon said as she returned to the bedroom. I could tell she wasn't upset but was very amused by the smirk on her face. I dropped the bra like a rock into my lap. I looked down to find a massive, five skinny inch erection sticking straight up. "No, no! Hold it back up. It looks like a little girl trying on her mom's bra!"

I followed her instructions and held her bra against my chest again. The soft cups were unfilled. She grabbed something and returned to the bathroom chuckling to herself. Meanwhile I found myself rubbing my nipples against the softness of the lacy cups. I couldn't help but I stroked myself. A clear bead of pre-cum appeared from my pee hole. I collected it on my finger and licked it with my tongue.

I could hear the water from the shower as I laid back in bed leaving Shannon's bra resting across my flat chest. I used my left hand to pinch my nipples hard; my left nipple was more sensitive than my right one.

"Oh fuck that feels nice!" I murmured. Then I spotted Shannon's strap-on cock. I grabbed it. The lube was too far for me to reach. I sucked on it to make it wet. I used the tip end to smear my spit into my hole then pushed her cock inside me. I was surprised when it slipped in without much effort. "Uuh!"

I continued to play with my nipples as I stroked my cock slowly to enjoy this new sensation. My eyes were closed. My head was pressed back into the pillows. My back was slightly arched. My fist held my shaft firmly. My hips thrusted my hand. My raised bum kept the cock inside me. "Oh gawd! Fuck!"

I started cumming. A long streamer of white goo erupted from my dick splashing my face and bra. I was still fist fucking myself. The next one was less long and landed on the bra and my belly. I kept humping until I was shooting air and collapsed back onto the bed. My whole body spasmed. "Oh gawd! Oh gawd!"

I opened my cum covered eyes and made out that Shannon was standing by the door watching. Well, more leaning against the door. One hand was abusing her full breasts while the other was finger banging her dripping cunt between her spread legs. "Auuh! Auuh! Auuh....!"

Juice trickled down the insides of her thighs as she came. Still panting, she pointed to her pussy. I came over, dropped to my knees and lapped her. After licking the dribble from her thighs, I used my tongue and parted her juice hairless lips. She came twice more before she pushed me away. I fell back on my ass; my face covered in slime.

Shannon smiled. "Well I guess I can't wear that bra full of your cum."

I laid back in bed as she went back to her drawer and pulled out a fiery red bra. She did up the front clasp and put on a crisp, white linen shirt. Even with only the top three buttons undone, you would be able to see her crimson bra and deep cleavage. She pulled on some black panties.

Thank goodness, Shannon hated pantyhose. She slipped her legs into a pair of rose coloured thigh high stay-ups before doing up the knee length, tight black skirt. The matching black jacket did little to hide anything. She slipped her high arched feet into a pair of patent red, open toed, four and a half inch high heel pumps.

A natural beauty, Shannon needed very little make-up; just a little red lipstick and she was set. She took the original black bra she was going to wear and placed it across my chest before she kissed me on the forehead and left for work.

I heard her Jag leave the driveway. I sat up to look at myself in the mirror but the bra just fell into my lap. I picked it up and wrapped it around my chest. I tried to do the back hooks like I had seen Shannon do it but it was a lot harder than it looked. I managed one, the other took much more effort but finally after a time, I was successful. I slipped my arms through the straps and thumbed them over my shoulders.

I raised my head and saw my reflection in the mirror. Even though her massive cups were empty, I loved the feeling of her bra around my chest. I played with my nipples underneath the cups and stroked my hard dick. Even though I didn't need to, I felt I wanted some stroking material. I jumped off the bed to her dresser. I pulled open the drawer where I knew she kept her dainties and immediately spotted a pair of black lace bikini panties. Back on the bed, I wrapped it around my shaft and used firm up and down strokes with my tight fist.

"I wonder...?" I slipped them on then I rubbed myself through the gauzy material. The roughness felt great against the underside of my pecker. The panties were low cut enough that the tip of my penis poked out the top.

The sensation was very different from using her panties as a stroker. My fingers went back to pinching my nipples. My other hand continued to rub my erection through the panties. My left nipple was like an orgasm trigger. I pinched it harder and harder. My hand took a firmer grip around my shaft as I pumped with much more vigour. Though I had dumped a large load earlier, I had managed to reload and started ejaculating. Not as much but just as hard. Spurts of white cum pool on my belly and inside my belly button.

"Oh fuck!" I swore to myself as my orgasm tailed off a bit. I collected my sperm with both hands; one smeared some across my chest and nipples, the other massaged it over my panties and pulsating cock.

I guess I fell asleep after that. When I awoke, it was almost noon. The cum was dry and crusty. Reluctantly, I undid the bra and pushed down the panties. Shannon already knew her bra was coated but I thought it would be best to wash out her panties. I held them up by the waist elastic; they were shredded. The delicate lace was not made for aggressive jerking off. "Shit!"

I threw them in the trash and hoped she wouldn't notice them missing.

I tried to relax the rest of the day but my mind seemed to drift back to my morning's jerk off session. I went back to the bedroom and found the bra I used. I found myself unable to resist the urge to wear it again. I stripped off my tee shirt and hooked Shannon's bra back on. "At least the wet cum has dried."

I pulled my tee back on. Of course, lacking any real breasts the shirt crushed the cups but still the feeling was indescribable. I went on line and searched for cross dressing porn. The amount of hits that came up was unimaginable. Then a video clip of pre-op Danielle Foxxx popped up.

The tall Brazilian was dressed in a black demi cup bra with her nipples left exposed. While her g-string was pulled aside, they would have done little to hide her package anyways. Danielle wore some stockings and garters which looked great in contrast to her beautiful, uncut cock.

I killed the rest of the day watching Foxxx videos and jerking off. I would have continued into the evening but I knew Shannon would be home soon. I closed my PC and reluctantly undid and removed my bra.

It was less than an hour before I heard Shannon's throaty car exhaust. The front door opened and she made her way into the house. She seemed very happy. "Sold that Anderson Street house today! That's the third one in less than a month. Commission should be great this month, better if it continues!"

She gave me a big fat kiss on the lips and a hard hug that squeezed the stuffing out of me.

"Congrats! That's great." I supported her knowing she'll spent a good portion of it on me.

"I know I won't get the commish until later but let's celebrate and go for dinner at that ritzy place." Shannon suggested.

"You mean the place we have to dress up for?" I really didn't want to dress up.

"Yes." Shannon confirmed. "I'm going to wash up then change."

As I got ready I could hear the shower going. I opted for a plane pair of slacks, an open collar shirt and a sports jacket. "That should be good enough for that place."

Shannon returned to the bedroom towelling her hair dry. She was naked as she entered. Her plump breasts swung freely. I could tell she just freshly shaved her legs and trimmed her cute little pubic bush. She grabbed a bottle of lotion from her table and shook it. "Shit! Empty. Be a hon and get me the other bottle in the bathroom?"

As I went to retrieve it for her, she tossed the depleted container towards the waste basket. Missed. Before I could react, she got up, picked up the bottle and dropped it in the garbage.

"Phew! She didn't notice. " I thought to myself as it was the basket I disposed her torn panties in. "Maybe should have thrown them out in a different container."

Then Shannon stopped. She looked into the basket and bent over to pick something out. It was black and lacy... her shredded panties. She held them up and inspected them; she took a careful sniff and then slowly turned towards me. "These are mine. They were perfectly fine and clean when I put them away. Why are they in the garbage?"

"Um... Er... I used them." I answered sheepishly.

"Used them?" Shannon questioned me.

I felt my face go flush. "I used them to masturbate with."

"Hmmm. Okay, how did they rip?" Shannon prodded. "Even if you just wrapped it around your dick, they should be torn like this?"

"I... um... wore them while I did it." I finally admitted. "At first I just used them to stroke with but wearing your bra at the same time, I was curious about how they would feel if I wore them."

Shannon's lips tightened and nostrils flared as she glared at me. Finally, "You owe me a new pair."

I watched a bit of the news as Shannon finished getting ready. She was gorgeous. Other than the heavier, red paint she had on her plump lips, Shannon was a natural beauty and needed very little additional make-up. She wore a mid-thigh length, tight, black dress. The front was a modest Vee neck but the back was bare and revealed enough to see down to the small of her spine. It would be impossible for her to have worn a bra. Unlike most of the times, her legs were bare; she wore no stockings. The shoes were black, strappy sandals with a four inch stiletto heel. Her bright red toe nails matched her finger nails.

"Whooo..it whoo..whee..el!" I let out a loud wolf whistle. "Wow. You look hot!"

Shannon broke a smile, then a glare. "I'm still a bit pissed at you for destroying my underwear. You owe me."

Since we would be drinking, we took a cab. I helped Shannon into the back passenger side, but as she sat on the bench, her hem raised further up her legs. I quickly ran to the other side and got in. Shannon did not bother to pull her dress back down. I leaned towards her to give her a kiss at the same time, I placed a hand on her the bare skin of her lap. She allowed me to kiss her but brushed away my hand.

Knot's Landing was a very old style, steak and seafood place. It was slightly light and had lots of old wood and heavy dark carpet. Most of the oaken tables were in the central floor area but the walls were lined with old style booths. All the seating upholstery was old brown leather. Shannon asked for a booth. We were lead to one that would accommodate three, but the waiter removed the spare setting. Shannon slid in first and sat with her back towards the wall. I slid in beside her to her right with my back towards the front of the house.

We were relaxing with a couple of drinks. I had a Johnnie Black neat while Shannon enjoyed her double vodka, spicy Bloody Caesar. I listened intently as she described the house selling event of the day. I didn't really say anything, I could just watch Shannon talk all day. We had another drink. Shannon looked around. As I tried to figure out what she was looking at, Shannon grabbed the hem of her dress and pulled it up around her hips. The long table cloth would hide any expose to the other patrons.

She was wearing a black, string thong. She spread her legs slightly and showed me the tiny sized, triangle patch barely covering her pussy. She pulled it aside. Even in the dim light I could see how wet she was. She collected some of her juice on her finger and brought it to my lips. I eagerly sucked it dry.

"Nice." She smiled. "Part of your repayment starts now."

Shannon hooked her fingers into the string waist and pushed her panties down her legs. She had to stretch down a bit to get them totally off, then in plain sight dangled them from her index finger in front of me. I snatched them from her quickly and looked around to see if there was any reaction. "What are you doing? People will see."

Shannon gave me a nonchalant look. "Now since you've agreed to take them from me, I want you to go to the bathroom and put those on."

"Wha...What?!" I was a bit taken aback.

"I am not in the mood to repeat myself." Shannon stared at me. She reached into her purse and pulled out the bra I had "used" earlier that day. She dangled it from her finger as well. "And this too. Go!"

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by Anonymous

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by DianeRedfern01/18/18

Hot start

Love the action and development so far. Can hardly wait for your next installment, sweetie!


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by STUGPOLE01/16/18

Quite enjoyable

This story has much potential, please do continue!
A wig, his own bra, maybe some breast forms?

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by Failedscout01/13/18

Great Start

Too short. Longer chapters would be nice.

Thank you for writing and posting here.

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