tagTranssexuals & CrossdressersCaught by my Sister Ch. 02

Caught by my Sister Ch. 02


I woke up the next morning still in a daze from the night before. My head throbbed from a nasty hangover as I attempted to remember what happened. As I turned over in my bed I felt something soft sliding against my skin. I lifted my blanket up and looked down at my body only to remember that I was wearing one of my sister's nighties.

It all came back to me like a bolt of lightning.

I remembered my sister Jane catching me wearing her clothes. She insisted on dressing me up and taking out to the party with her. I couldn't believe that my first ever kiss was with a guy, Alex, who I ended up giving a blow job to. I remembered meeting Matt in a dark bedroom and we both lost our virginity together while I licked my sister's pussy.


I needed coffee.

I pulled myself together and put on my robe before heading downstairs to the kitchen. In the living room I saw my mother lying on the couch and slowly remembered fucking her while she was passed out.

What a night...

I tried to be quite as I passed the couch but she noticed my anyway.

"Good morning Suzy."

Suzy? I didn't even realize that I was still wearing the red wig and make up from last night.

"Good morning Mrs..."

"Don't be silly, call me Erica. I must have had quite a night last night. Would you mind helping me upstairs? I'm still a little woozy."

"uhhh sure, I'd be happy to."

I walked around the couch to help my wobbly mother up, but paused when I noticed that her short skirt was still pushed up enough that I could clearly see her pussy. I did my best to be discreet, but she caught me anyway. Our eyes locked briefly before I looked away embarrassed.

I helped her up off the couch and put my arm around her as she clung onto me as we walked up to her bedroom. I opened her door and she stumbled in on her own. I stood in her doorway as she turned around to face me. I froze as she began unbuttoning her blouse right in front of me.

"Did you girls have fun at your party last night?"

Since I didn't know how girls acted when they were alone with each other I tried to act casual as if this was all very normal to me.

"Yeah, it was fun. I'm a little hung-over though."

My mother unbuttoned the final button and her blouse spilled over her shoulders and landed in a pile at her feet fully revealing her incredible breasts to her horny son.

"I think we all are a little."

She pulled on the zipper on her skirt releasing it to join her blouse in a crumpled mess on the floor. My cock started to swell inside of my sister's panties as I stared at my mother's incredibly sexy naked body. I tried not to be obvious but I couldn't take my eyes off of her.

She walked across the room as she said. "It gets lonely being a single mother sometimes. Do you ever get lonely Suzy?"

I stammered "I guess everyone gets lonely sometimes Mrs... Erica."

She opened up her nightstand and pulled something out as she continued "Do you know what I do when I get lonely. Every girl needs a little friend."

She turned around facing me and held up a small pink plastic wand that I could only guess was a vibrator. She turned the end of it and I could hear a gentle humming sound. Her hand drifted down her bare stomach and she touched the tip of her vibrator to her pussy.

"ohhhh. Sometimes my little friend is all I need, but sometimes I need a little more help. Do you want to help me Suzy?"

Without saying another word she moved over to the bed and positioned herself with her back propped up against her pillows and her legs spread wide apart as she pushed her vibrator inside of her pussy.

My own mother was masturbating right in front of me. My cock was now straining against the thin fabric of my Jane's panties itching to be free.

I followed her lead and moved to the foot of her bed. I crawled up onto the bed between my mother's legs and enjoyed the close up view of her fucking herself inches from my face. I could already smell her aroma as I moved closer.

She pulled the vibrator out and presented her dripping pussy for me. I could still taste her on my lips from the night before. My tongue slowly pushed against her hot pussy.

"Oh YES. Lick me Suzy!"

She still tasted like a mixture of her own juices mixed with my cum and whoever else she had fucked the night before. My tongue traveled the length of her pussy up to her clit. I pushed into her with my tongue as I slid two fingers inside of her pussy. Her hips bucked beneath me when I entered her. I bit and sucked on her clit while I fingered her as her body writhed in pleasure.

Her pussy clamped around my fingers as she came. Her breathing quickened and she thrust her hips into my hand as her body shuddered.

"Oh my god Suzy, that was amazing."

I didn't say a word as my head rested against her thigh. She wrapped her hands around my face and pulled me up on top of her. She released me as our mouths met. Her soft lips pressed against mine as we kissed. Her hands slid down my body and opened my robe.

Oh shit! How can I stop her?

I felt her grab my cock through my panties and start stroking me. I made a surprised noise into her mouth as she grabbed my cock.

"Aren't you going to fuck me now Suzy? Don't you want to fuck your mother again?"

Everything was happening so fast at this point that I didn't know what to say. She pulled my cock out of my panties and before I knew it I felt something warm and wet pressed against it. I didn't hesitate and thrust my hips into hers penetrating my mother with my hard cock.


I no longer cared about anything. I slammed my hips into hers and forced myself deep into her tight pussy. I was so horny at this point that I felt like I was about to cum after only a few thrusts.

My cock swelled inside of her as I released my first stream of cum.

"FILL ME UP WITH YOUR CUM SUZY." She kept screaming in ecstasy as I came.

I pushed deeper into her as I shot another load of cum. I ground my hips into hers as I finished cumming and then rolled off of her to catch my breath.

As I lay there in her bed she turned to me and said "Don't be surprised Suzy, I've always known that you like to dress up in mine and Jane's clothes. I've just been waiting for you to be open about it. Now it's finally just us girls in the house."

I was speechless, I was just seduced by my mother who was happy to have my finally be open about dressing like a girl. What have I gotten myself into?

"I don't know about you Suzy, but I need a shower."

My mother rolled out of bed and headed off to the bathroom leaving me alone to think about what just happened.

I stayed in her bed for a little while before deciding that I needed a shower myself and went down the hall to the bathroom I shared with Jane. When I got out of the shower I was surprised to find another outfit already laid out on my bed.

This outfit consisted of a pair of floral print leggings with black lace trim at the cuff that came halfway up my calves and a loose fitting cream colored sleeveless button down blouse. I was surprised to find that there were no panties or even a bra laid out for me. Next to the pile of clothes was the same red wig and a pair of high heels.

I put on my new outfit and went downstairs for breakfast. My sister, Jane, and mother, Erica were already seated at the kitchen table chatting over cereal when I walked into the room. The soft lycra of the leggings stretched snuggly around every contour of my legs and ass; but more importantly it gently blanketed my cock and balls allowing them a combination of support and freedom as I walked. I was enjoying the way the fabric clung so tightly to my body as I strode across the house.

"Good morning Suzy." Jane said with a twinkle in her eye.

I could tell that she and my mother were reveling in having me dressed up like a girl. I never would have expected that they would be getting as much enjoyment out of it as I was.

"Good morning." I replied as I poured myself a bowl of cereal.

"Eat up Honey, we have a lot to do today."

I looked up at my mom unsure of what she meant.

"I got a call from Patrick this morning. We planned on going out again tonight but he wanted to know if I had a friend that I could bring along for his friend. I couldn't think of anyone else I would rather go on a double date with, so I told him that I knew just the girl. But we have a lot of work to do today to make sure you don't blow your cover tonight."

"That's not all she'll blow tonight!" Jane couldn't resist.

Both of them laughed at Jane's comment as I sat there blushing, but also excited about the prospect for that night.

After breakfast we got up and Jane and my mom watched me walking around in the heels giving me tips on being more graceful. As I strutted through the living room I was starting to get a little excited and realized that my penis was creating an obvious bulge in the front of the leggings.

"That is a problem." My mom said as she pointed right at my crotch.

"We need to figure out a way to keep that under wraps.

"I have an idea."

Jane walked up to me and pulling down the front waistband of the leggings she grabbed my penis in her other hand pushing my semi-erect cock down between my legs.

"If only we could keep it pressed down like this it wouldn't be nearly as obvious."

My cock was getting harder as my sister struggled to hold it in place.

"Come on Suzy, you're not exactly helping the situation here."

Her hand was now wrapped around my hard shaft as my cock stood at full attention.

"I can't help it. It feels good when you hold my cock."

Being a young man, my libido was on fire. When I had the house to myself I had been known to jerk off four or five times in a single day. I didn't know what to do.

Fortunately, my sister didn't wait for me to come up with an idea. As I stood in the middle of our living room with the leggings pushed down around my thighs Jane knelt down and took my cock into her mouth in one swift motion.

I closed my eyes and let my head fall back as her warm lips enveloped my rock hard cock. Instinctively, I moved my hands to the top of her head as it bobbed up and down the length of my cock.

When I opened my eyes I saw my mother sitting on the edge of a chair watching her daughter suck my cock. Her bathrobe was completely open and her hand was between her outstretched legs rubbing her pussy.

The sight of my mother masturbating for the second time in the same day was so hot that I immediately came in my sister's mouth. I heard a muffled noise when I released my first shot of cum into her but she continued sucking and licking as I emptied myself into her.

After she finished and pulled her mouth off of me she stood up and pulled my face to hers. Her lips pressed against mine as our tongues touched. I felt something warm in her mouth and realized that her mouth was still filled with my cum. Our tongues swirled and danced in a pool of my cum as she kissed me. Slowly I felt that she was pushing my cum into my mouth with her tongue. I didn't resist and soon my mouth was full. She pulled away from me leaving me with her sweet taste on my lips and a mouth full of my own cum.

I looked over at my mother as I swallowed my cum and saw that she appeared to have two fingers buried deep inside of her pushing her to another climax.

Jane took my soft penis and tucked it into the leggings as she pulled the waistband back up around my hips.

"Much better, now nobody can tell you even have a penis."

The rest of the morning and afternoon progressed with more lessons on walking and talking like a lady as well as tips on makeup. Before I knew it Jane and I were in her bedroom getting me ready for my date while my mom got herself ready in her bedroom.

After trying on several outfits, Jane and I settled on the silver dress she wore to her junior prom. The top of the dress is a shiny material with a wide strap that goes around the neck and leaves the shoulders bare. The top only shows a little cleavage since it was made for a high school girl. Below the chest line the dress flairs out into a thin matte silver material.

Jane gave me a red strapless bra with her silicone inserts. The material of the dress came up just enough to cover the top of the bra and was tight enough that my chest looked very realistic.

Because I am several inches taller than my sister, the dress that probably came down to her knees didn't even go halfway down my thighs. Jane gave me a pair of red silk panties to match the bra and a pair of silver high heels that only covered my feet with three thin silver straps at the toes and ankles.

Jane also gave me a thin silver ankle bracelet, which I put on my right ankle, and a pair of clip-on earrings.

We had just finished up when my mom walking into the room and said that they would be here for us any minute and that we should wait downstairs.

Before leaving my sister's room my mom turned to me with a smile that covered her face from ear to ear and said.

"Oh Suzy, you look so beautiful! Are you ready for our date tonight?"

"I think so."

"Ok, let's go down and wait for the guys to get us."

We left my sister and I followed my mom to the living room with butterflies in my stomach.

My mom was wearing a very short black dress that had a plunging neckline which made it perfectly clear that she wasn't wearing a bra.

As I walked down the stairs thinking about the night that lay ahead and feeling the silky material of my sister's dress gliding across my bare skin I was starting to get turned on again. By the time we sat down on the couch I had a full blown boner, which didn't escape my mother's attention.

"Suzy, not again!"

"I'm sorry; it just feels so good to dress up like this."

"It's Ok. But I guess we need to do something about this, and we don't have much time."

My mother abruptly got up from the couch and walked around to side. She bent over propping herself up with her arms on the arm of the couch.

"Come on and let mommy help you out with you little problem Suzy."

I didn't skip a beat and quickly positioned myself behind her. In her position her dress left little to the imagination and I could already clearly see her purple thong panties. I lifted up the back of her dress and stared at her firm round ass as I pulled her panties down enough to expose her sweet pussy.

While I held her panties off to the side with one hand I used my other hand to hike up my own dress and release my cock from my panties. I stepped closer and my penis brushed against her soft pussy hairs as I pushed the tip of my cock against her. She adjusted herself by pushed her legs further apart to give me easier access and my cock slid right into her waiting pussy on my first thrust.

"OHHHHH" She let out a moan as I penetrated her.

My cock effortlessly slid in and out of her sopping wet pussy as I pounded her. I tried to move fast knowing that our dates would be there soon. I was pumping my cock into my mother as hard and fast as I could when the doorbell rang.

We both froze for a moment.

"I'll get it." My sister flew down the stairs stopping briefly to look at us as she passed through the living room.

I stood here holding on to my mother's hips with my still hard cock buried deep inside of her. Every movement of hers made her pussy squeeze my cock pushing me closer to the edge.

We could hear Jane talking to our dates inviting them in to sit in the formal sitting room while they waited for us to get ready.

"Don't stop now Suzy!" My mom snapped.

I slowly started fucking her again quickly increasing my pace to a furious pounding. I couldn't believe that I was fucking my mother like this while our dates were waiting for us in the next room.

"OH FUCK!" She screamed as her pussy tightly gripped my cock. I exploded inside of her as her pussy pulsated to the rhythm of her orgasm.

I pulled away from my mom and tucked my soft penis back into my panties while she pulled up her panties and fixed her dress.

She turned to me "Ready?"

"I think so."

"Just relax and have fun tonight, ok?"

"I think I can do that." I said with a tilted smile.

Our dates were patiently waiting for us as we walked into the formal sitting room.

"Is everything ok? I heard you scream."

"Oh, that was nothing. I was in such a hurry I just stubbed my toe.

"Well, you two look gorgeous."

For our date we went to a new 'luxury' movie theater that just opened up in town. The big draw of this place was that the seating area was sectioned off into semi-private zones each with a soft leather couch big enough for four people and a waist high privacy wall.

The movie playing that night was a cheesy romantic comedy that none of us were too into and before long I looked over and saw that my mom and her date were making out next to us. By this time my date had his hand on my right thigh and was caressing my leg. I took my mom's lead and turned to him. He saw his opening and our lips met. Kissing another man is very different than when I kissed my mom or my sister. He was much more forceful and took the lead. I let his tongue enter my mouth and explore, doing my best to follow his lead. His hand moved further up my leg as we kissed but I knew that I had to stop him.

My mom's date was now on the ground between her legs pulling down her panties, which gave me an idea.

I slipped off the couch and knelt between my dates legs, pushed his knees apart. I managed to get his belt buckle opened, but needed his help with the button on his pants. After a brief struggle I had his pants around his ankles and let my hands explore his thighs like he did to mine. His legs were a little hairy and not nearly as soft as mine. I slowly moved my hands up his thighs until I reached his cock. I took it in one hand and his balls in my other slowly, gently massaging him as I lowered my mouth onto him.

His cock wasn't very big and I had no problem fitting all of him into my mouth. As I sucked him off I could see my mom enjoying the tongue bath that she was receiving from her date. I wondered if he was enjoying the taste my cum.

I turned my attention back to my date and gently tugged on his balls as I sucked and licked his hard cock. I would tease him by pulling my mouth up so that only the tip of his cock was in my mouth and then used my hand on his shaft while I flicked his tip with my tongue before pushing my mouth back down onto him burying my nose in his thick pubic hair.

His grunts, which started soft, were getting louder and more frequent as I fucked him with my mouth. I sensed that he was getting ready to cum and started working him faster and harder. His cock swelled up in my mouth and shot a stream of hot salty cum into me hitting the back of my throat. I did my best to swallow his cum but it just kept flowing out of his mouth that I could barely breathe.

Eventually his river of cum subsided as his penis grew soft in my mouth. I licked the rest of the cum off of him as I pulled my mouth away but remembering my experience from earlier in the day with Jane I had a twisted idea.

Using my hands on his knees I pulled myself up and crawled on top of his lap until I was straddling him. I could feel his soft cock pressing against my own cock through my panties. Thank god I fucked my mom before our date otherwise I would be rock hard by now. I leaned into his face and pushed my mouth to his. We kissed for a moment before he realized that I still had some of his cum in my mouth. My mouth wasn't as full as Jane's was when she did this to me, but it was obvious that I was pushing something into his mouth. At first he hesitated and then he submitted to me as he ate his own cum out of my mouth.

I felt his penis getting hard again as we kissed and slowly started to grind my hips and my soft cock into the base of his growing penis.

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