Lori Lux Pt. 06: Sissy Motel Room

I began to realize if I hosted I could more easily embrace the sissy side, but it wasn't easy sharing a space with other people. I received an interesting proposition in an email that gave me a solution I had not yet considered.

I was talking with a man who had never been with a sissy or even a man. He couldn't host and neither could I. He suggested I get a room at a nearby motel, dress up and he would give me cash for the room. This was a perfect idea, my mind was already imagining the sex. I agreed.

I packed a backpack with slutty clothes, make up, my black wig, my recently bought dildo, condoms and lube. I got a room with access from the parking lot and began dressing. I chose to wear just a black bra and a full fishnet bodysuit with a hole around my sissy pussy. I applied my make up with blue sparkly eyeliner and red lipstick. I looked stunning I thought.

I was so horny from dressing I couldn't resist, I lubed up my sissy pussy and pulled out my 6" realistic dildo. I inserted it into my hole and moved it back and forth slowly. I continued until the familiar feeling of warmth occurred and it became effortless to slide the toy in and out. Now I was ready for anything I thought.

I put the lube and condoms on the table across from the bed and invited my date over.

He now seemed to be less enthusiastic and had cold feet. He was worried we might know each other. He asked if I could blindfold myself. I agreed that I could. He said he would visit me in 15 minutes.

I put the deadboIt out. I got on my hands and knees on the side of the bed with my ass high in the air. I tied a black knee high sock around my face as a makeshift blindfold. I waited ass in the air, blind to the world.

I heard the door open. This is kind of hot I thought. He sees me exposed, but I can't see him. I heard steps and the sound of a zipper being pulled. It sounded like he was right close to me now. I heard him rummaging with the condom packaging. I felt great knowing he was already hard just looking at my sissy ass.

It was quiet for about half a minute and then without warning I felt his cock push into my sissy hole. He didn't bother with the lube. I was glad I had loosened myself up previously. He slid right in first try easily. He pushed in all the way. I could feel his jeans against my ass. He felt fairly average sized all around. He began to slide back and forth inside my hole keeping his cock buried deep the entire time. His rhythm was a little weird. He seemed nervous and inexperienced. About a minute in he began to fuck me harder and faster. I thought, "now he's gettin--"

"Oh fuck!" he said. I felt his cock tense up inside me. He sighed loudly and pulled out. I heard him zip up his pants and the door shut.

I took off my makeshift blindfold. He was gone. There was a discarded condom on the table by the bed. He did not leave the money either. I was a little disappointed that I let myself get tricked, but I was more disappointed that I spent time, money and effort for about a minute of anal sex.

Then I considered I still had the room until morning. I put the used condom in the trash. I put on my red dress over my fishnet body suit and invited another man over. One of the old pervs I had been chatting with through email was glad to come visit me. He would warn me about safe sex, but ultimately loved my pictures and stories.

He was 62 years old and a bit chubby. I adjusted my make up and awaited his arrival. He showed up in sweat pants and a t-shirt and a small cloth bag. I was laying in bed trying my best to look seductive. He kicked off his shoes, rested the bag down on the table and laid down beside me. He got a big grin, "It's nice to meet you Lori."

No one had ever called me Lori in person before. It felt right. It made me feel like a slut. "It's nice to meet you as well, Rick.", I replied

Rick reached his hand out and started rubbing my body through my dress. "Very sexy sweetie." he said. I outstretched my hand and began rubbing the visible bulge in his sweat pants. "Good girl." he reinforced.

He pulled down his pants and revealed his cock. It was 5" long, thick and cut. He was wearing a ring around his shaft and balls. I wasn't naive and knew what it was for but had never actually seen one before. I slid down in the bed and began to suck his cock.

His cock was very hard. Likely from the ring. It stood straight up at attention while I sucked with just my mouth. I rubbed it all over my face. "You like daddy's cock don't you?" Rick asked.

"Yes, daddy." I replied.

"Go look in the bag." Rick said. I got up from the bed and opened the bag. Inside was a school girl lingerie set and a pink chastity cage. "Wear it!" he instructed.

I went to the bathroom to change. The lingerie set was a plaid skirt, a skimpy white shirt and some white knee high socks with cute little bows. It was a bit small, but that made it sexier. I heard a knock on the bathroom door. I opened it dressed as a school girl. Rick walked in fully naked. He looked pleased. He spun me around looking intently. He hugged me from behind. I could feel his rock hard cock against my ass.

Rick started to position himself so his cock was close to my sissy hole and then hump into me. He turned me towards the counter. I could see him behind me in the mirror. His balding hair, his big smile and his chubby chest full of hair. Rick then pushed down on my upper back, naturally forcing me to bend over. His hard cock still pressed up in between my cheeks. He began humping me from behind again.

His cock started to work it's way inside my sissy hole. I was really glad I prepared first thing in the hotel room now. He worked his way in further and further as we made eye contact in the mirror. He pulled my cheeks apart and spat down on his cock. He began aggressively ramming it into me. He fucked fast and hard. Pushing all his body weight into my ass. It felt amazing. Looking at him in the mirror I could tell Rick was actually very muscular under his layer of body fat. He had strength and a stamina I hadn't felt before. Something primal in me like that. He grabbed my waist and pulled me back onto his cock with an extreme strength.

"Daddy's going to teach you a lesson, slut!" he said in my ear while holding me tightly by the waist so his cock was completely buried.

"Yes daddy please!" I replied.

"Daddy knows his school girl sissy slut likes to get bred." he said still with his cock forcibly held into me.

"Yes, I love it!" I replied.

Rick let go of my waist and grabbed my chest. He pulled me back up towards him. He kissed my neck. His cock still remaining in my ass despite the awkward position. My hard cock visible now in the mirror. "That will not do!" he said grabbing my cock.

"Sorry daddy." I replied, unsure what to do. He grabbed the chastity cage. He put the ring around my balls and forced the top on pushing it hard onto my erect sissy cock. He kept it clamped together with his hands and then put a little lock through the pin. It was not comfortable. It felt like it was pinching my skin and my cock was extremely uncomfortable.

He ran hid hands back up to my chest. "That's a good school girl." he said smoothly and kissed my neck again. He pushed me back down into a bent over position and began ramming his thick cock into me again. I felt a warm sensation radiate out from my ass. My cock was going limp and it was starting to feel good in the cage. Now the tension was off it was no longer pinching. It made a thocka thocka type noise every time he rammed into me. I broke my gaze from the mirror and looked down at my caged cock. The sensation was incredible. I watched as a long stream of cum leaked out the hole in the cage. I was having a sissygasm. I felt his hands grab my head and pull me back up to look at him in the mirror.

"Daddy's going to breed you now slut!" he said. He pushed hard into me, "holy fuck!" he bellowed. He started spasming and twitching. I could really feel his load erupt in me. He pulled out.

"Thanks Daddy." I said fully embracing him as my owner.

"Don't thank me yet, the lessons not over." Rick said as he used a towel to wipe off his crotch. I stood up confused.

"Only daddy breeds you!" he said. He walked over to the garbage can and pulled out the used condom. He tied a knot in the top of the condom. "I see you've started having safe sex, but daddys girl is only a breeding whore for him, understood?"

"Yes daddy." I replied.

He grabbed the remaining 5 condoms off the table. "Show me all 6 used condoms and I'll let you out of the cage sissy."

"Yes daddy." I replied again like a submissive automaton.

Rick dressed himself, "now get to work sissy." he said and left out the door.

Sitting alone, I pondered for a while. Realistically I could just pull the cage off even though it was locked. It was basically just hard glossy plastic. It would probably hurt a bit, but nothing is actually forcing me to go through with this. I could just rip it off and never talk to Rick again. That's what any sane rational person would do I thought, but I didn't actually want to do that. Collecting used condoms did seem weird, but the experience I just had was everything I fantasized about. I was going to follow through with Ricks request.

I put the used condom in my backpack and invited over another man I had been chatting with. He was a 28 year old athletic guy. Still wearing the school girl outfit I waited for him on my knees on the floor at his request.

He walked into the room, didn't say a word. He just pulled down his pants and walked towards me. I began sucking his cock on my knees. Looking up at him. He was handsome. His cock was very average in every regard. I could feel Rick's cum leaking out of me slowly while I sucked this strangers cock. I felt like a real sissy slut. The stranger finally spoke, "bend over."

I rotated 180 degrees and put my hands down onto the floor. He slipped out of his pants. I felt his hands pull apart my cheeks. Worried that he'd see Rick's cum leaking out of me I tried to distract him, "There's condoms on the ta--"

He was already inside me. My sissy pussy gave no resistance at all. He was sliding in and out of me fast. He reached around my waste and grabbed my cage. He pulled on it like he was trying to pull it off. "No... d-don't!" I mustered up. He let go of it. He now started really ramming into me. Pushing me farther and farther into the floor. Before I knew it he was laying on top of me still sliding his cock in and out of my sissy ass. My cage rubbing against the carpet with every thrust. He grunted loudly and stopped thrusting. I didn't feel him cum, but I know he just did. Ricks task was going to be harder than I thought.

It was getting late now. I wasn't sure what I should do. I asked Bob to come visit me, but it was to late for him. I decided to try one last stranger.

A hefty man in his 40s walked in the door. He was wearing a pair of dirty jeans and a sweater. I was still in my school girl outfit laying on the bed. He stripped out of his jeans. His cock was shriveled. He laid down beside me, I began to kiss and lick around his cock. It grew a bit. He had micro cock. It was probably around 1.5 inches and not very thick. He didn't say a word as I sucked on his tiny cock. I knew I wasn't getting my second filled condom from this guy, but a good sissy serves. I sucked him until he blew his load in my mouth.

Feeling deflated I decided to go home. It was 1 in the morning. I did not see the point in staying the night. I took off my wig and wiped off my make up. It was still visible, but I was tired. I put my street clothes on over top my school girl outfit. I locked the key in the room and headed home. On the walk home I noticed my cage made a noise when I walked. A slight jingly noise.

I entered the common area of my dormitory. Tom was still awake watching TV on the couch. He looked up at me. "Fun night?" he asked.

A feeling of embarrassment flooded over me, "yeah." I responded quickly.

Tom stood up and got between me and the door to my room. "Are you wearing make up?" he asked.

I paused for way to long. "I was, yeah." I admitted.

Tom laughed a bit at my answer. I felt my cheeks getting warm. "Why?" he asked.

I wanted to tell him, but I was also afraid. I had done an excellent job keeping my two lives separate so far. Tom was a bit of a jock. He was a popular guy on the basketball team and had girlfriend. He wouldn't understand.

"What's in the bag? Studying late with make up on?" he said prying farther.

Tom started walking towards me. I felt my voice shake, "I was on a date." I felt my sweater being lifted off. Tom had pulled it off of me and was now looking at my hairless body wearing a black bra and a tiny white shirt.

"One of the neighbors said a sexy girl was at our place one night... It took me a while to realize it was you." Tom said. My embarrassment peaked. I didn't say anything. "Don't worry." Tom said as he opened the door to my room. I walked inside and he followed closing the door behind him.

I removed my pants and revealed my plaid skirt. The cum inside me and run out and leaked down my legs during the walk. "Wow, your date made a mess of you." Tom observed. He turned me around and looked at my ass. "That's so fucking hot!" he said. He slipped out of his gym shorts. He had a semi. I turned around got on my knees and got to work. Tom was big. 7", cut and smooth shaven. I began throating his big cock.

"Holy shit, you're good at this!" he complimented me.

I took his cock out of my mouth and slapped it against my face, "thank you." I replied. I got up, grabbed a new condom out of my bag and got on the bed. Tom laid down on his back beside me.

I put the condom on his hard cock and got on top of him. It slipped into me without protest. All the previous cum working as a lubricant. I sat all the way down on his cock and began riding. "Holy shit man." Tom whispered. Tom began to arch his legs up and push into me as I was riding down on him. It was blissful. "Oh fuck, I'm going to cum!" Tom clenched up. I felt his cock pulse inside me.

I got off slowly. I removed the condom and kissed the tip of Toms dick. He got up and said, "Don't tell anyone about this."

"Of course." I replied. I added the second filled condom to my collection. Four more to go I thought. I slept like a baby that night.