Sissy Maid to Mom and Sister Pt. 05

I was cleaning the spot on the living room where mom had given Liz an orgasm using her mouth and Liz had squirted all over the floor when I felt tired and had to sit down for a moment. All the excitement of the day had taken a toll on me, and it was catching up to me. As I sat down on the couch for a moment, I noticed that my anus was throbbing. I couldn't sit down correctly, it hurt so bad. I was grunting with discomfort, trying to find a position on the couch that didn't hurt, when I heard mom's voice.

- Does it hurt too badly?

- Yeah, a little bit. -- I said trying not to show too much pain on my face.

- I'm sorry about that. -- Mom said, before lowering her eyesight. She seemed deep in thought. She then lifted her head and called out for my sister. -- Liz, please come down.

Liz had gone up to her bedroom after having given me an orgasm in the laundry room. She was making the plans mom had told her to, like inviting the guest to come over.

- Hang on, give me a sec -- Liz said into her phone as she came out of her room and leaned against the rail from the upper floor to address my mom -- Yes, mom?

- Let's postpone the plans for now. Bring the analgesic from my nightstand and come down to have a talk as a family, please.

- But I was just telling--

- Please, Liz, just do as I say. We'll have time later on to have fun, but, for now, do as I say. -- Mom turned towards me with a caring look on her face.

- Ok, mom. -- Liz said before turning towards her room and putting the phone back to her ear and proceeding with her call -- Yeah, sorry. My mom just told me we're gonna have to...

I couldn't listen more of her conversation as she entered her room.

Mom came towards the couch and took my hand.

- Come here, son.

I noticed she was no longer referring to me as a girl. I got up, following her instructions and she kneeled down in front of me. My mom kneeling in front of me with her face towards my crotch seemed like something that would turn me instantly, and the idea of it happening did, but the pain from my asshole made if impossible for me to have an erection and my thoughts were split between feeling sored and wanting to have more sex.

My mom put her hands under my French-maid outfit and pulled down my thong. I guess it was ok to consider it mine, already, although a few hours ago it was hers.

- Turn around, sweetie. -- My mom used her hands to direct me to turn around in place.

As I did, I felt exposed, even though a few moments ago I had been in the same position, only I was on all fours and my mom was pushing her finger inside my asshole. I felt a kiss on my butt cheek. My mom was kissing my ass. Then I felt another, and another. One more, but this one felt wet, as my mom opened her mouth and used her tongue. She started tracing a path with her tongue towards my asshole, though it made me a little nervous as I could still feel my butthole throbbing. Mom split my butt cheeks with her hands, which caused me a little discomfort, but then I could feel the tip of her tongue on my asshole. It felt soothing. As my mom's tongue covered my hot throbbing asshole, I could feel the trace of cool spit easing my pain, just to be reignited a second or so after her tongue had left that space.

- It feels so good, mom. -- I said when it hit me that my mom was licking my asshole. This time, I could feel a little bit of blood rushing into my penis.

Mom grunted and continued as she was doing so far.

I heard footsteps coming down the stairs and turned to see Liz coming down with her phone in one hand and in the other a small white tube.

- Here, mom. -- Liz stood next to my mom and put into her hand the tube.

- Thank, you, sweetie. -- Mom stopped licking my ass and unscrewed the cap of the tube.

Liz let herself fall onto the couch that was next to us and started texting on her phone. Mom put a covered the tip of her right index finger with the substance in the tube, which I remembered was analgesic, and started rubbing it onto my asshole.

- Usually, we apply this before penetration so it doesn't hurt so much the first times. -- My mom was rubbing my asshole with a bit more gel. -- But I was so caught up in the moment I forgot to ask if you had done this before. By the look on your face, I could see you hadn't.

- Well, not exactly. -- I said, blushing a little because I never thought I would ever share this with my mom or sister. -- I had once put my finger up there. It hurt a bit, but I also liked it. I just hadn't experimented more with it.

Mom spurted a bit more of the lube on her finger and she was tracing circles around my asshole. It felt really nice. The pain was almost gone.

- One is not supposed to use so much because it then renders you numb to feeling anything, which is not what you want when you're going to shove a dildo up your ass, but we're gonna rest now, so it's ok to use a bit more. I'll just put a bit more inside.

I felt mom's finger starting to push in me, but it was not as painful as before. I actually kind of liked it, though, she was right, I was starting to lose sensation, until I could no longer feel anything.

I felt another kiss from my mom on my butt cheek and then saw her rise to her feet.

- Well, now you can rest a little bit. Sit down for a little bit and, when you're ready, go up to your room to lay down. I'll leave some clothes on the bed for you to put on.

- Thanks, mom. -- As I turned, I didn't know how to show her my appreciation, and I ended up by giving her a hug.

My mom responded to my hug and, when she broke it, she gave me a kiss on my mouth. A big one. With her tongue caressing my lips.

- I'm feeling excluded here, you know? -- Liz said as she stared at us.

Mom turned to her with a big smile on her face and leaned down over her, still sitting on the couch, and put her hands on Liz's cheeks to pull her closer and give her an even bigger kiss. I could see them twirling their tongues around.

- It's your brother's special day, Liz. -- Mom said as she broke from the kiss with a tone so sweet, that I had only ever heard from my mother when she was talking to us. -- Be sure to be extra nice to him, too. I'm sure he'll be more than happy to reciprocate any signs of affection.

With that, mom glanced my way, still wearing a huge smile on her face, and then headed upstairs.

I sat down next to Liz. It was easy, as my asshole was not throbbing anymore, but I did still feel exhausted and bit sore from my knees. I could only guess the intense adrenaline rush I had experienced by being intimate with my sister and my mom was finally receding, leaving me tired.

- How did you like it, lil' brother? -- Liz put her phone away and turned to me. -- I bet you feel tired, but really happy, don't you?

- I do. -- I said, with a smile on my face. -- I imagine you must know what I'm feeling.

- Of course. Having "Lil' Johnny" shoved up your ass getting oral to cum? Yeah, it's a really nice feeling.

- It is. -- My smile grew even wider. Then, a sudden realization came to my mind. -- Sis, is the name supposed to be a joke?

- What name?

- Lil' Johnny. I mean, he wasn't little by any means.

- Oh, you're so adorable, lil' brother. I can tell you that no, it is not sarcasm for me to call it lil. My other toys are bigger. Maybe I'll let you see them some day. Not all of them, of course, as I still like to have my personal toys, personal, but who knows? Maybe It'd be fun to see which one of us can get stretched more.

I felt a little bit nervous at the idea of having something even bigger rammed up my asshole, given how sored I had felt before mom put the lube on me. And this nervousness must have shown on my face because Liz laughed at my expression. She then hugged me and rested her head on my shoulder. I looked down at her and saw the contrast of her head against the French-maid uniform I still had on. I rested my head on top of hers and said in a whisper:

- Thank you, Liz, for being so nice to me. I love you. I love you so much.

- I love you, too, Andy.

I was so comfortable in this position; my eyes were shutting by themselves. I was feeling like I was beginning to fall asleep, when my sister added:

- It feels so good to finally be able to share this feeling with you as well.

I hugged my sister and gave her a big squeeze, before she continued:

- You should go upstairs to your room and have some rest. I'm sure you'll feel like a million bucks after you wake up.

- Yeah, I'm sure you're right.

I kissed my sister on the top of her head, and then she looked upwards to me and closed in on me to give me a kiss on the mouth. Unlike my mom, Liz's kiss was slower, as if she were savoring every crevice of my mouth with her lips and tongue. She broke our kiss and got up from the couch just to head upstairs to her room. I followed after her, but split towards my own room.

On top of my bed, I saw mom had laid out for me pink knickers with a little bow at the front and a pink matching bra with wires under the cups. There was also an almost transparent pink gown. A teddy, that was to be used on top of the underwear.

I removed my dress, and underwear, and tossed it on a pile in the corner of my room, then dressed up in the attire my mom had chosen for me. They didn't seem to be new garments. I thought it was from her personal clothes at first glance, but something told me it may have been from my sister. I liked the idea to dress up in my sister's panties and bra, complemented with the pink teddy.

As I put on the knickers, I understood why mom didn't chose a thong for me. I felt a bit shaven and sore on my ass crack from having the thong all day long and moving around in it. I had never thought that it must be painful for women to wear those kinds of underwear all day long. Probably why on their days off I usually saw mom and Liz wearing big baggy pants and sweatshirts, and sometimes when they bent down, I could see they wore big cotton panties. It must be comfortable to give the body a break.

I put on the teddy, and the fabric was so soft that I could feel all my skin tingling. I could imagine the feeling like electricity firing up all my sensors and increasing my sensitivity to touch. I laid down on my bed and started caressing all of the clothes I was wearing. I was so tired I didn't realize the moment I fell asleep.

The sound of clacking woke me up some time later. I recognized it as the sound cutlery makes against plates. Liz and my mom were surely having dinner. It was around 8 in the evening. I went downstairs and saw mom sitting at the kitchen table and Liz leaning against the counter next to the fridge. She had an apple on her hand. In front of mom, on the table, there was a steaming cup with a spoon next to it. Probably what made the sound that woke me up. They both turned to see me when I entered the kitchen and I saw their gazes look down my feet and back up to my face. They were checking me out using the teddy and underwear mom had left for me before I went to bed.

- Hi, sleepyhead. You look adorable wearing my panties and bra. -- Liz smiled at me.

- He surely does. -- My mom added before sipping on her coffee.

- I certainly love the feeling of these clothes against my skin. -- I said before I sat down on the chair next to my mom's.

- I know, sweetie. -- Mom put down her coffee and turned to me, putting her hand on top of my high. -- Men's clothes are usually comfortable, but women's clothes make you feel so much more. It makes you feel sexy.

Liz sat down next to me and I smiled to her. It felt nice to be wearing women's clothes out in the open. I felt so good.

- Let's talk about all this, shall we, sweetie? -- My mom continued. -- As you may have guessed already, Liz and I have had more time being intimate with one another. It's been a couple of years already that we discovered that we wanted to show that we loved each other with more than words.

Liz stretched her arm across the table and reached mom's hand and they both squeezed tight while staring into each other's eyes.

- Three years, actually. -- Liz added without breaking eye contact with mom. -- But I had made advances towards mom even before that time.

- You had? -- I asked with curiosity.

- Yes. -- Liz turned for a second to see me, then returned her gaze towards mom. --

A couple of months after I hit puberty, I sensed what it was to feel turned on. I saw the boys and I could only think about having their arms around me, smelling their scents and feeling their penis against my hips, my womb, and especially between my legs.

Liz blushed a little and then turned towards me.

- But the thing is... - Liz continued -- it didn't happen only with the boys. I found myself fantasizing with women too. When I saw my teachers, like Mrs. Givens, I imagined what it would be like to have her hands cup my breasts, and fumble around with my clit. When I got closer to her in class, with the excuse of having her explain to me something on my notebook, her scent gave me desires of kissing her and put my hands on her hair, feeling our tongues touch each other and lay naked for her on a bed. Being at her mercy and having that blonde tall woman do anything she wanted with my body. Smell it, touch it, taste it. Feeling like she owned me and desired me.

Liz let go of my mom's hand and crossed her hands on top of her lap. She looked towards the floor and continued with a lower voice.

- I had all this desires, but I felt like a bad person for having them. I thought if anyone would ever find out I fancied women, I would be the laughing stock in school. I'd lose all my friends. They would all see me as a freak. I cried in my room and tried to will myself to not have these feelings towards other women. I punished myself every time I had a fantasy with a teacher or women from the magazines mom sometimes bought. Until one day mom found me in my room. I had been crying and she knew it.

- I did. -- Mom chimed in. -- I had known for a wile you were passing through difficult times, but I hadn't imagined they would be that kind of problems.

I turned to see mom and she had a look of compassion I had never seen before. I could see just the memory of Liz suffering because of her own nature still brought crushing feelings towards her.

- Mom held me tight and asked me what was wrong. -- Liz looked directly at mom with tears filling her eyes. -- And I couldn't keep it a secret anymore. I told her I felt bad because I found women beautiful and wanted to be with one. I hugged her and must have cried non stop for a very long time. I squeezed really hard on her because I was afraid mom would reject me, too, but I needed her so much that it all just poured out of me in that moment.

- It still breaks my heart thinking of my little girl crying because of who she was. -- Mom had a tear trail down her cheek. -- But I told her that there was nothing wrong with her. She was beautiful just the way she was and she was not alone. I also had those feelings. I loved looking at women, hence why I on occasions would buy some fashion magazines. And I loved being with men, too.

Liz's face was red and had shed a few tears, but she was smiling while looking directly into mom's eyes. Then she continued:

- Mom told me to be proud of myself. To accept me for who I was and to never let any fear of judgment make me think any less of myself. She told me to rejoice in the feelings I had with men and women and to never feel alone or unwanted because of these feelings. So, I did just that. I kept having fantasies with Mrs. Givens and with pretty much anyone else I found attractive. I was a happier person, I accepted myself, and I felt so close to mom to be able to share my real me and have her accept me for who I was. So close that on my eighteenth birthday I told her the wish I had wished when blowing the candles on my cake. I told her I wished for her to be the first woman I made love to. I wanted to give her my innocence while we made love.

- I said yes, of course. -- Mom said, this time looking at me. -- But I told her she had to be sure about it. I told her to wait one week, to think it over and made sure it was what she wanted. Meanwhile, I was making preparations to have her special night be as special as one could be.

- And indeed, it was. - Liz said. -- Of course, I didn't change my mind over the course of one week. I just wanted her more. I saw her and she was so beautiful. I fantasized about my mom entering in my room and kissing me while undressing me. By that time, I had managed to get a hold on some vibrators. I had been masturbating almost daily and each time I was able to reach an orgasm. It was such a beautiful feeling that I couldn't think of anyone more deserving to share this than with my own mother, my own family. The woman that gave me life and had loved me since day one. I wanted to tell her that I loved her in a way that was special and intimate. To let her know that I loved all of her and wanted to be near her.

- And she did as much. -- Mom was smiling and looking at Liz. The she turned to me. -- Our first night together it was magic. I was able to see my daughter have the most intense smile and she did the same to me. Over the years we have grown closer and we have been together on more occasions that I can recount.

There was a moment of silence on the table. Mom was happy, as was Liz, and they hadn't let go of their hands.

- I can't believe I never knew what was happening. -- I said. Suddenly, I was feeling left out. Like I was from another family. My face must have shown my sadness.

- Don't be sad, Andy. -- Liz intervened. -- We didn't forget about you.

- Really?

- No, we didn't. -- Mom told me. -- We've been aware that you too were special for a while now. Although, we didn't know what was it that made you feel good with yourself. I never found an opportunity to approach you because it had to come from you to share this with us, not from me.

- Well, as of lately we kind of figured out what it was that you liked. -- Liz exhaled as she threw her gaze up. She was remembering. -- A couple of weeks ago, I noticed some of my clothes were not where I had left them after I threw them in the hamper. At first, I thought it was mom that took them. Maybe to put them on... or maybe...

Liz turned to see mom with a mischievous smile.

- You thought I was using them to masturbate? -- Mom asked with genuine surprise on her face. -- I must admit sometimes I thought about it, but I preferred to have you, sweetie.

- Well, a couple days ago, - Liz carried on. -- we were talking about if we should let you in on our family dynamic. I mean, first we waited until you were eighteen and had gotten to know yourself a bit better. Then we decided that we would approach you about the subject in a couple of months. Given that you're really quiet and introvert, we weren't sure where you were on the process of understanding and discovering your sexuality. But things, turns out, have a different way to unfold as to what one plans.

Suddenly I became very aware that I was wearing girl's clothes in front of my mom. That I had exposed to them the most intimate part of my being. But, most importantly, that I felt ok with this.

- So, earlier, - Liz snapped me out of my own thoughts. -- when I told you that, if you wanted my panties, you should have just asked for them, I was serious.

I remembered the scene of Liz finding me masturbating with her underwear on.

- Well, I... - I was having trouble forming sentences. -- I didn't... I mean... You were... I just... - I let out a big sigh. -- I was afraid you were going to be mad at me, or be ashamed of me. I thought it was wrong to have these urges, so I always tried to hide them.

- I understand, lil' brother. -- Liz extended her free hand towards me. -- I really do.