Some of my stories are true, or at least, based on actual experiences.  Others are complete fantasy.  This one starts with an actual experience and turns into a fantasy of how I wish it would end. 

I never get as much “gurl time” as I would like.  It seems when I dress, the time flies by too fast.  So, when I get the rare opportunity to get away from my captive male life for more than the usual few hours, I make the best of it.  In this case, taking the hours required for a complete transition including nail polish, make-up, hair removal, fragrant bath, and a wig.  This also results in thirty to forty minutes returning to my male appearance at the conclusion of my gurl experience.  As you can see, a large portion of time is required in an attempt at some passability and a rewarding experience.

A few weeks ago, one of these opportunities presented itself where no one would be home over the weekend starting on Friday.  A further stroke of luck was my employer decided to shut down operations on Friday.  The final part of the “perfect situation” is the adult bookstores finally reopened as the pandemic restrictions were relaxed with the condition that a mask was required.  However, this could only be enforced during entry into the bookstore and exiting.  Once in the theater, many would remove their mask at various times.  Looking at this from a positive perspective, it was easier to conceal my gender identity, similar to Halloween. 

With the house to myself, I started late Friday morning getting ready.  I applied Nair hair remover, with aloe and lanolin to my legs, chest, and lower abdomen before wiping off the hair with a washcloth.  It makes my skin feel so soft afterward.  Then, I took a hot shower shaving my underarms and face.  The steam from the shower softens my facial hair giving a clean shave that lasts longer.  I gave myself an enema with a premixed drug store product.  Next, I took a warm bath in a premium bubble bath solution soaking for over an hour.  I rubbed lotion on my hands and feet to keep them soft and smooth followed by deodorant under each arm.  Then, I brushed my teeth and gargled with mouth wash.

I sat down at the vanity in the bedroom and applied a gloss pink nail polish to my toenails, then to my fingernails.  I’m always amazed at the instant feminization I feel with nail polish, especially pink.  It took fifteen or twenty minutes before I was satisfied my nails were dry enough to continue.  I wanted to prepare as much as possible, but keep in mind that I had to leave the house as a man.

I went into the garage and retrieved my secret gurl bag, bringing it to my bedroom.  From the bag, I pulled out and put on a full front black lace thong.  Oh, what a feeling.  Next, I put on a matching well-padded black lace bra.  Then, I put on a pair of slightly stretching tight short pants that fit snuggly on me.  For my exit from the house, I put on an oversized long shirt over my skimpy sheer white blouse.  Since no would see my feet in the car, I put on a pair of ladies' flat sandals that exposed my painted toenails.  I finished by putting on a sparkling wrist and ankle bracelet. 

I packed my carry bag with the remaining items I needed for my adventure, finishing with a few dabs of perfume on my neck.   I brought all of my things down to the garage.  I took my wig, breast forms, and make-up case from my gurl bag and put them on the front seat.  I put my gurl bag in the car trunk for safekeeping and put my carry bag on the floor on the passenger side before getting in the driver's seat.  Then I opened the garage door with the remote, started the car, and backed out of the driveway as I waited for the garage door to close completely before driving away.

I drove a few miles to a local park where there were several parking areas, finding a spot with some privacy.  I pulled my oversize shirt over my head and discarded it on the back seat before slipping the set of breast forms into my bra cups.  Then using the rearview mirror, I put on eyeliner, make-up, eyebrow pencil, and the most difficult of all, lipstick.  Finally, I put on the wig and combed it out.  In spite of all this preparation, I’m never satisfied that I’m passable.  It would be impossible to tell anyway looking into a small rearview mirror.  However, I had the added insurance of wearing a mask.  I immediately felt more comfortable after putting it on and looking in the mirror.  As I looked at the time on my cell phone, I couldn’t believe it was already four o’clock. 

I decided to step out of the car and walk a little bit since there was no one around the area.  I left the mask on. It felt so wonderful to be outside fully dressed like a real woman.  This was a chance to practice walking.  I almost always wear flat shoes.  I have seen many cross-dressers wearing high heels that clearly gave away their male gender.  They actually looked ridiculous when they walked.  The term “female impersonator” comes more to mind than CD.  The flat shoes are comfortable and make a feminine walk so much easier adding to the credibility.  They make me feel more feminine and that’s my biggest thrill.

After walking for ten or fifteen minutes, I got back in the car and drove to the adult bookstore about twenty miles away.  Fridays are always the best.  It is usually their busiest day.  I took one last look at myself, put my keys in my carry bag, and got out of the car, both nervous and excited.  There were at least a dozen cars in the parking lot already, which is situated in the rear of the building.  Discretion is apparent in the entire layout of the premises.  I walked to the entrance in my best feminine walk.  Once inside, I briefly looked at some of the items in the store before going to the counter and handing the clerk my ten-dollar bill.  He handed it back saying, “No charge for women, Honey?” as he buzzed me through the theater door. 

This was a great start to the day.  I’m not sure if he knew I was a man or not, but I was at least good enough for free admission.  As I stepped into the theater, I was immediately blind from the change of daylight to almost total darkness.  I saw a few shadows standing in the hallway before the door completely closed, so I only walked a few steps before stopping to let my eyes adjust to the darkness.  I put my hand up in front of me to feel my way to the wall when I felt someone.  In a whisper, I apologized, “Sorry, I really can’t see in here yet.”

A male voice responded, “That’s okay, honey, it happens to everyone when they first come in.  You can stand with me until you can see better.  Or, longer if you’d like.”  He took my hand guiding me against the wall next to him.

I responded back, “Thank you.  That’s sweet of you,” as I squeezed his hand a little.

After a few minutes, he started stroking my hair a little with his hand.  I turned to him and smiled.  I guess there was enough light for him to see my face as he began to move his hand down my back feeling around my bra as if the smile was permission to proceed.  I love the feel of a man’s hands on my body.  When his hands reached my waist, I stepped in front of him with my back to him.  I moved back a little pushing my ass against his crotch.  He gave me a little kiss on my neck.  This always drives me crazy.  I leaned my head back giving him more access to my neck and placed my hands over his.  He wrapped his hands tightly around me pushing his cock into my cheeks.  We just stood there in that position for a while as he continued rubbing his cock on my ass.

Then he asked, “Well, have your eyes adjusted to the dark?  Would you like to check out the theater?”

I softly said, “I can see better now.  Lead the way.”

He took my hand leading me down the booth lined corridor toward the theater.  I noticed a few other men following us.  I have been to this bookstore many times in the past attracting little attention.  Tonight I felt like the “Belle of the ball”.  When we entered the theater room, he led me to the back corner where there was a round table.  He looked around before saying, “You’re attracting a crowd here tonight.”  I sat up on the table opening my legs a little. He stood facing me stepping in close to me between my legs as he rubbed my shoulders a little.  I reached for his crotch and began rubbing his cock through his sweat pants. 

His cock began to grow and harden from my gentle messaging.  I could hear a voice behind me telling another, “She is one hot chick.”  There must have been two additional sets of hands on my back probing around my waist and bra straps.  I thought to myself, do they really think I’m a woman.  I don’t think I was ever this excited before.  I pulled my guide’s jogging pants down a little to free his now hard cock.  Slowly, I started jerking him off with both of my hands.  He was fairly endowed. 

There was little more I could do in this position, so I spun around laying on the round table on my stomach with my head hanging over where I could suck the dick I was working on.   I pulled my mask down and began to lick the pre-cum from his tip.  The extra hands were rubbing my butt cheeks and my back as I licked with earnest.  Then, I felt my oral subject put his hands on my head to urge me to take his dick in my mouth.  I obliged him.  I wagged my tongue on the bulging vein on the underside of his dick as he moved it in and out between my lips.  My hands were cupping his balls.

One of the hands on my butt began moving down the back of my legs.  This is another turn-on for me.  I could feel the hand push harder as it was working its way between my legs.  I instinctively opened my legs bending my knees with my feet up.  The hand immediately started rubbing my crotch.  Someone yelled out, “How does her pussy feel?”  The hand seemed to still be probing, unsure of what it was feeling.  With all this arousal, my dick was still soft and tucked tight in my thong. 

My attention now shifted back to the cock in my mouth that was now taking long strokes.  I moved my hands from his balls and wrapped them around his waist pulling his cock into my throat.  He held my head forcing the end of his dick to go as deep into my throat as possible.  I had to push him back as I began to gag for air.  I could hear him give off a little groan as he declared, “She has a deep throat.” 

Once, again my attention shifted to the hands on my ass.  They began to pull down my shorts and thong.  I could feel multiple sets of hands as voices kept commenting on how hot I was.  Finally, one of the hands hit pay dirt stating to everyone, “She has a dick.” 

Another voice retorted, “She’s still hot. If you don’t want her, leave her to me.”  I liked that he was still referring to me as her.  He climbed up on the table and sat on my ass as he asked, “Do you like to be fucked, baby?”

I pulled my head back off of the dick in my mouth and replied, “I love to be fucked, but you must wear a condom.” 

He responded, “No problem.  Do you have one?”  I reached for my carry bag and fumbled for one.  I held my hand behind my back with the condom and a tube of lube.  I was quickly reminded I was in the middle of a blow job at the same time as the hands on my head pulled my mouth back on his dick.  I put my hands back around his waist and pulled him into my throat, again, holding him for ten or fifteen seconds, before withdrawing.

As I took a breath of air, I could feel the top of the lube tube being pushed up to my rosebud, followed by a cold injection into my hole.  As the tube was backed out, the lube squished between my ass cheeks.  The warm cock that began to probe for its entrance was a welcome relief to the coldness of the lubrication.

I pulled the cock back into my mouth messaging it with my lips and tongue.  Suddenly, I felt the dick head begin to enter my hungry ass.  As it slid deeper into me I had to let out a moan despite my mouth being filled with another cock.  I was in ecstasy.  The only thing better than a cock is two cocks. 

I could feel the weight of the cowboy on top of me settle on my ass.  I knew he was in as deep as possible.  He started bucking which made me move up and down on my mouthful of cock.  The excitement took over and I began pulling the shaft in and out of my throat. The hands on my head were becoming frantic and more forceful.

Then, I heard the familiar crying out, “Ahhh, Ahhh, Ahhh!”  The vein against my tongue began to pulsate as it pumped its load into my throat.  The hands on my head held me tight.  My hands were gripping his waist.  I could feel a warmth in my throat.  I was on the verge of gagging so I reluctantly had to push him back a little.  Now I could taste his cum as his dick was dribbling some of the remains in my mouth.  After he pulled it out, he squeezed his hand from the base of his dick to the tip producing a large drop of cum which he rubbed on my lips.  “You’re one hot woman,” he said before disappearing.

I could now concentrate on the activity inside my ass.  He continued at the brisk steady pace he started with.  I was getting hot and dry from his constant pistoning in my tight ass.  His hands were gripping my waist as his hips gyrated like a mechanical device.  I pushed my hips up to give him a little more depth while I squeezed my ass muscles and closed my legs tightly.  He reacted with a long groan and harder thrusts.

“Here it comes sweetheart,” he announced as he held his last thrust pushing me forward a few inches.  I could feel his cock throbbing inside me.  He bucked a little as he blew his load.  Then, he pulled his cock out leaving me feeling empty. 

After dismounting me and climbing off the table, he gave me a little pat on the ass. He parted saying, “You’re better than any woman I’ve ever had.  Thank you, dear.”  I pulled up my thong and shorts.  I stood up feeling quite good with a taste in my mouth and my ass sticky from the lube.  Unfortunately, my thong was becoming uncomfortable from the mess.  I moved into the dark corner of the theater, removed my tight shorts and thong, replacing them with a full coverage panty and a loose, but still skimpy pair of shorts.

There was a clock on the wall near the hallway.  It was only six o’clock.  I still had the whole evening ahead of me.  I put my mask back on and walked down the corridor to the other end where there is another large room with a big screen, sofas, padded benches, and a large padded seating area in the corner.  I sat down on one of the sofas. 

Over the next few hours, I watched dozens of men come and go.  I’m not sure of their interests.  I have come here often without getting any action.  I guess some are not into cross-dressers.  It is amazing how you can be the center of attention one minute and a wallflower the next. 

After a few hours, another cross-dresser came into the room and sat next to me on the couch.  She asked, “How are you tonight, Sweetie?”

“I’m okay.  How about you”

She replied, “I’d be better if I could find a real man tonight.  The men in here are so fickle.  You never know what they want.  Have you had any action tonight?”

I told her about my experience earlier.  She said she was going to walk around before patting me on my leg, getting up, and walking down the corridor.  I sat there with my legs crossed waiting for something to happen.

Eventually, the other cross-dresser came back into the room with a man.  They both sat down on the large padded area in the corner. He pulled his pants down and she started to suck his dick.  After a few minutes, she crawled up on the padded area on all fours.  He got on his knees behind her for some doggy style anal sex.  Suddenly, she cried out,” Please, Daddy, go easy.”  Then she says, “Daddy, you’re hurting me.  I want it, but you have to start slow.”

I grabbed the lube out of my bag, walked across the room, and climbed up next to her as I told her, “I think you need a little help, dear.”  I opened the cap and squeezed some lube on her ass.

The man began to penetrate her, again.  She started to whimper a little, “Easy, daddy.”

I moved in front of her, pulled my mask down, and put my arms around her.  She embraced me tightly as I asked, “Is that a little better?”

“Yes, thank you so much.  You know I wanted this, but sometimes it hurts.”

“I know, I know,” I said sympathetically as I looked in her teary eyes.  We held each other as she was being fucked in the ass.  It didn’t take too long before the man shot his load and then disappeared. 

“I have to use the bathroom.  I’ll be back.”  She kissed me on the cheek and left.  I put my mask back on and went back to my spot on the middle of the sofa on the other side of the room. 

A few minutes later, a middle-aged black man sat next to me.  “Hi, I’m James.  How are you tonight?”

“I’m fine.” 

He smiled at me before he pushed his hips up a little and pulled his pants down to his knees displaying a probably seven or eight-inch cock.  I rubbed his leg a little, and then started using my fingers to feel the tip of his dick.

“Your fingers are soft.  What’s your name, Honey?”

I like to use a female name that is not associated with my real name so I replied, “Chrissy.”   I continued to stroke his shaft and balls lightly with my fingertips.  My hands looked so feminine with the pink nail polish.  I was enjoying the feel of being a woman as I seduced this man.  I thought to myself, “I’m so naughty.”

As I continued, he relaxed letting his head lean back against the cushion.  After a few minutes, he said, “You can suck that if you want.  No pressure.”  I pulled my feet up next to me on the couch and pulled my mask down so I could lean down and kiss the tip of his dick.  He quietly said, “Your lips are so soft and warm.”

I rolled a little toward my stomach and took him into my mouth.  He had a soapy taste as if he just showered.  I licked up and down his shaft, and then pushed his dick into my throat once.  He responded with a gasp.  I bobbed up and down a few times stopping to lick the tip in between.  He stroked my hair and rubbed my shoulders as I serviced his cock.  After a few minutes, I sat up to rest for a minute.  He put his arm around me and kissed me on the cheek.  I crossed my legs with both feet touching the floor.  This is significant for me as it is the way a woman often sits.  There are many things I do when dressed that add to the illusion of being a woman.  I can see the difference in my movements and the female impersonators.

As we sat there, the other cross-dresser came in and sat on the sofa next to us.  She smiled as she said, “Thank you so much, dear.”  I turned my attention back to my man, rubbing his leg and put my head on his shoulder.  He whispered in my ear, “What would you like to do?”

I whispered back, “I’d really love you to fuck me.”

He responded, “Where would you like to go?”

“I’m fine right here, if it’s okay with you.”

While he looked a little surprised, he said, “I’m okay with it if you’re okay.”

I pulled my carry bag off the floor, reached in for a condom and the lube, and handed them to him with a look of anticipation on my face, I’m sure.  He put the condom on and rubbed some lube on it.  I climbed up in his lap and pulled my shorts and panties down in the back.  Then, I positioned myself for him.  He tried several times to penetrate me, but couldn’t seem to get in my tight ass.  Finally, he said, “I think we’re going to have to bend you over.”

He stood up and I got on the couch, doggy style, leaning on the armrest with my head toward the other cross-dresser.  She turned sideways and put her arms around me as we did earlier as she said to James, “Start easy, don’t hurt her, she’s a friend of mine.”

He put the tip of his cock against my ass as I guided it to my entry.  Slowly he leaned against me and pushed.  My sphincter slowly expanded letting him penetrate me this time.  As he started to fill me I began to let out a small moan.  The cross-dresser looked into my eyes as she asked, “Are you okay, honey?”

“Ohhh yes,” I answered with a smile on my face.  She smiled back at me.

James put his hands on my waist and gently pulled himself inside me as he asked, “How does that feel my dear?”

“It feels so good, stud.”

I could feel his balls against my ass when he was as deep as he thought he could go.  I pushed back instinctively leaning my upper torso down a little taking in a few fractions of an inch more.  This was more of a signal to him that I really wanted it badly.  He pulled back a little and pushed in, again.  With a slow and methodical rhythm, he continued to fuck my ass like we were old lovers.  His hands moved up and down my waist, occasionally straying to my back. 

I spread my legs open more to give him better access and stability.  This was the most affectionate sex I’d ever experienced from a man before. I pulled from the cross-dresser’s embrace and raised my body upright, still on my knees.  James wrapped his arms around me across the front of my bra with his hands on my shoulders.  Hugging me tightly, he used his hips to move his cock inside me.  I kept pushing my ass into his crotch with every thrust he made.  His lips were nibbling my one ear as I could hear and feel his heavy breathing.

He strained out a whisper in my ear, “You are so hot and so tight.  You’re unbelievable!”

I thought to myself, let me show him what tight really is. I squeezed my ass muscles as I have done so many times before.  His response was immediate, “Oh my gosh, you’re making me come.”

I could feel his cock pulsing inside me.  He hugged me tight, “Chrissy, you’re the best.”  Then we both leaned over together as I rested my head on the arm back next to the cross-dresser.  James still had his arms around me.

The cross-dresser said to me, “You make it look so satisfying; I wish I could fuck like you.  Thanks for taking care of me earlier, I have to go.”  She put her finger on her lips and then on mine as she got up and walked away.

Watching her walk across the room, I realized there were a few men standing around that were probably watching us the whole time.  James was rubbing my back with his cock still in me.  I let out a quiet moan to acknowledge my appreciation.  After a few more minutes, he pulled his body back letting his cock slither from my ass.  I so appreciate men waiting until they soften a little before pulling out since it doesn’t leave the emptiness it does when they’re still hard.  He pulled up my panties and shorts as I reached for some paper towels from my bag and handed them to him. 

He wrapped the paper towels around his cock and pulled off the condom. Then he picked up the wrapper and walked to the trash can on the other side throwing away the mess.  When he came back, he put his pants back on and sat next to me.  “You’re so wonderful, Chrissy.” 

“You’re pretty good yourself, James.”  He put his arm around me rubbing my shoulder and stroking my hair.  “What, no slam-bam, thank you ma'am?”

He replied, “You deserve better than that.”

With that, I laid my head on his chest and snuggled against him.  I was melting in his arms.  I never felt like this before.  It was a new level of femininity.  I pulled my legs up on the couch and put my one arm around him.  As he continued to rub me, I started rubbing my hand up and down his legs. I felt like a real woman in a man’s arms. 

He asked me how often I came here and if I lived nearby.  I didn’t want to sound like a whore, so I told him I only came here once in a while.  I also didn’t want to give away my identity telling him I lived about forty-five minutes away.  We talked like a couple of young lovers for a few minutes when the room suddenly lit up.  It was closing time.  They turn on all of the lights inside so they can make sure everyone leaves. I wanted the night to go on forever. 

As we walked toward the exit, James asked me, “Will I see you, again?”

I answered, “I hope so, but I don’t know when.  I don’t get much time out and this part of my life is a highly guarded secret.  It is rare that I get an entire weekend like this.”

His face lit up, “You have the whole weekend?”

“Yes, I do.”

“Would you like to stay with me at my apartment tonight?”

This was a dream come true and at the perfect time.  There was no one at home to know if I didn’t come home tonight, I had all of my gurl wear in the trunk, and James was the perfect gentleman who treated me better than anyone in the past.  It only took me a few seconds to say, “Okay, I’ll follow you.”

With that, he walked to his car, which was the only car other than my own, at this point.  It was a BMW.  I quickly went to my car and got it started to assure I was ready to follow him.  It was only about a twenty-minute ride in the opposite direction of my house.  I pulled in next to him at his upscale apartment complex.

I popped the trunk so I could get my gurl bag and then grabbed my carry bag.  James quickly offered to take one of my bags for me which I declined.  He opened his front door and we both stepped inside.  When he turned on the lights, I realized this was the first time someone actually had the opportunity to take a serious look at me in the light.  I was nervous as hell until he leaned in and gave me a kiss as he said, “Chrissy, you look even more beautiful in the light.”  I wasn’t sure if he was just saying it to be nice, but I didn’t care.  I knew he still wanted me.

“Let me show you to the bedroom in case you want to freshen up.”

As we stepped into the bedroom and I looked at the bed, I also realized that in all of my years of cross-dressing, I was never in a real bed with a man.  Was I dreaming?