Our Second Encounter

Another story written by femdoll jona.

This is Story number 2. My very first story is called "Finally in person"

Our Second Encounter;

The day had arrived and I was flying in to my Mistresses town. It has been nearly 6mths since I have seen my her in person and I was ready for another fun filled week.

Of course as I am a submissive sissy, I am not 100% sure on what will occur and have already signed a contract stating my obedience and acceptance to Mistress Jae's term. The contract has been completed and agreed on my both parties and we have both acknowledge the Hard limits to our adventures

For me transforming from my male persona (Married male, father of 3) to a sissy femdoll, who is open to almost anything, and is exciting to say the least, especially when I am 'jona' I love being as slutty and free as I can be, she really loves being humiliated and Mistress Jae know this.

My training has persisted with hypnosis videos and audios, story reading, completing tasks and progressing with youtube tutorials. The previous weeks I was told to load my phone with sissy hypnosis files, involving lingerie, cock sucking, public humiliation, dildo fucking and being a slut for cum.

Unlike my last visit, I was not greeted by my Mistress this time, however had been given simple instruction. Travelled into town arrived at the hotel around 6:30pm, checked in and headed to my room. Had a shower, got cleaned up, was shaven and smooth, and ready to take on the persona as sissy jona.

The travel plans and meet ups have always been organised, we have a friendship that works in both realms, vanilla and kinky, but for this trip there will not be a lot of vanilla play.

After check in, showering and drying, I messaged Mistress Jae, and inform her that her sissy has arrived and just got out of the shower.

Her response was fast, like a pre-typed message:

Welcome back my sissy slave. A few rules for this trip.

1. Be honest at all times

2. Your clitty must be in a cage from now on, if not on already. Put it on NOW...

3. Your pussy should be clean and lubed and plugged, do this NOW...

4. I will be at the car park of your hotel in 30min.

5. We will go for a drive and talk about the week ahead and what's to cum on this trip. (not you 😊)

6. Put on your open crutch black one piece body stocking and school girl skirt

7. Then cover them with your boy clothes.

8. Also carry with you a small bag, with your redish wig, black eyeliner and red lipstick

9. This is the start of your feminisation, and you will always have feminine undergarments on while here.

10. Will be good to see you Darling jona, don't be late. 30min.. GO.

Dress in the lingerie always excites me, so putting on the chastity cage is always the first step, which was already unpacked. Clicking the padlock closed, I understand that what was left of my male persona was now confined to this cage and not coming out for a week.

Jona's male form has finally accepted this lifestyle and has been willingly wearing the chastity cage for well over 2 years, getting smaller and smaller rings and juggling it between days at home and wearing it to work, including with family and having to take it off before his wife noticed it. (He doesn't get to sleep with his wife a lot, so can manager lengthy period with it on.

After packing my small bag with the required items, I finish sliding on my body stocking, feeling it hug my body I slide on the mini school girl skirt and adjust it so it sits on my hips and in the right location. Cage on, body stocking on, Skirt on, bag packed, I move to the final step and getting the plug ready to fill my ass-pussy. Already clean and with a little lube I work it in and out until I can slide it all the way in. Once in place I pause, smile and know this is the beginning of the trip as jona.

My minds drifts to my sissy thoughts. 'I wonder where we are going, what does she have planned for tonight and this week' getting excited, I snap out of it and do a final check to make sure I have everything, I re-read the message and mentally tick off all requirements.

I grab my jeans, socks and shoes and place them on, followed by a T-shirt that just covers the sleeves of the body stocking. 15min have passed and I need to get a move on.

Scanning my room, I quickly unpack my travel bag, hanging clothes into the cupboard, remove my sissy clothing and items and store them in the bottom of the cupboard. I close the nearly unpacked bag and move it to the corner of the room. I am ready.

When I reach the 25min mark, my phone pings, notifying me my Mistress had sent me another message.

I have arrived, see you soon my darling sissy.

Grabbing my bag, I put my 2x room card in it with my wallet cash and ID if I needing it.

I walked out and headed to the carpark.

As soon as I reached the car park I was greeted by my Mistress. Like me she to was wearing casual clothing and after a hug and some small talk for about 5min she said 'Get in, sissy' with a huge smile on her face.

As we drove around for about 5min with some further small talk. She pulled over on the side of the road and started to talk.

'sissy jona, while in my company for this trip I have told you that you will be a sissy the complete time. I accept that at times you will need to be in your male form, like you are now, but will need to be 100% sissified underneath. Do I make myself clear? I nodded and verbally replied "Yes Mistress"

You have continued with your sissy transformation and have completed some milestones, however you have really been progressing to slow. I am a caring Mistress but you need to care more about my needs to, when I give you tasks you should be completing them a lot faster than you currently are. Do you understand? Yes Mistress, I am Sorry Mistress, I will do better' I responded.

This week I will be increasing your training and as you have no family or kids or work to use as an excuse, you will do what I ask. Nodding I accept. You will be a sissy, you will do as I wish and I will have fun watching you complete what I say. Are you sure and 100% you want to do this?

Without hesitation, I nod and say "Yes Mistress, I know I have been slack and make stupid excuses, please help me with my transformation, make me a sissy, humiliate me, please Mistress. I will do as you wish.

Mistress simply showed her approval as she smiled from ear to ear and said" I will gladly do all those things " however first stop is going to be a park I want to scope out for some sissy walking in a few days.

Mistress went on, 'Being a Wednesday night, I want to see how busy it is on a week night, as last Saturday when I checked it out, it was pretty packed with lots people. I want to see where you can walk in your full attire and not get interrupted. I want to be able to take some photos of you promoting your sissification in a public place. I'm happy if a few people see you strutting you stuff but not family's and kids. If it is good tonight, then tomorrow night it is public humiliation for my sissy.

You pulled into the parking spot in front of a park and I could only see 1 other car which had a couple in it, chatting to each other. The rest of the park looked quiet.

The evening sun was already down past the horizon and the ski glowed with the evening light. The park was illuminated by small lights on lamp posts spread out along a walking path. We got out of the car and I quickly offered to open my Mistresses door but she laughed and said Next time.

Before she locked the car, Mistress pulled out a large feminine shoulder bag and said hand me your bag and took all my contents out and placed them in her bag. This is a sissy bag and not a male back pack. The bag was heavier as I started to look inside, Mistress replied it has 2 water bottles in there if we get thirst. I put in on my shoulder and we walked towards the path.

Moving down the path the park had some really dark spots, you could still make out BBQ areas with tables and chairs, some with small shelters and some in the open. We continued to walk and only noticed a few people walking around, possibly 8-10 people max.

After about 5min of walking, we walked off the path towards one of the sheltered BBQ areas. When we stopped I asked if my Mistress would like a drink and started to take the bag of my shoulder. As I placed it on the table Mistress commented on how I feel about walking here in my full transformation tomorrow night. I stopped and looked at her. She was smiling and I smiled back saying; "Mistress, I will do as you wish, I came here to see you and to be guided by you, you are my strength that helps me stay focused on my sissification transformation, and being with you in person is a dream come true by itself. You excite me, and yes I sometime shy away, but I know I will love it. I would love to walk with you in public dressed like a sissy. It will be a new form of humiliation but would be an honour to do it by your side."

What about now, would you take your man clothes off here and now. I simply nodded. 'Good, Go on then, take it off now my good sissy'. That's 1 gold star for you already.

I removed my shirt, shoes, socks and jeans and then realised I wasn't instructed to put panties on, so now I stand with my sissy pussy full with a plug, my sissy clit encased in its chastity and my smooth shaven body covered with a black body stocking with a small school girl skirt.

Mistress just laughed, 'feeling sexy my sissy'. She walked forward ran her hands over my body, pitched my nipples one by one through my body stocking, then grabbed you caged clitty. Ohh you poor little thing, you are not going to see the light of day this week but Im sure you will get excited and try to get hard.... She let out another laugh.

Do you feel sexy darling? You look good enough to fuck.

Would you like me do a little video of this. Looking at the ground I said "Yes please Mistress".

Looking up Mistress already had her phone out pointing at me, at first a few flashes then she started talking. Here I am with my sissy, once a man but now a sissy cock slut. Tell me what you are?

I looked straight at the camera and replied "I am sissy jona, I am being transformed into the sissy slut I need to be, hope you like what you see. I want to be a sissy cock slut" Hear that men, this sissy wants cock, who's interested.

I was so horny and now in the mood, I stopped for a second and reflected on what occurred and then realised I had no make up on and was still looking like a male wearing some lingerie.

I didn't say anything for a while, as I looked around It was darker but we were clearly alone and no one else in ear or eye range.

While I stand there, Mistress said 'Yes please, Ill have that drink now.

I open the bag and unzip it reaching inside to grab the water, feeling around I felt my wig, and I think lipstick, or 2 or 3 similar size items, Rope and a water bottle.. no its not water it is a dildo. I looked at her and said there isn't any water in here.

Tip it out on the table. All of it, now sissy.

I lifted the bag and tipped it gently as the content fell out.

As I felt, the items fell out, a small towel, my wig, there was a roll of rope, a dildo, yes the 10' dildo Mistress fucked me with on our last encounter, that was fitted to her leather strappy harness. A small towel, my red lipstick, eye liner, a tube of lube, a few black marker pens and some rolled up black material.

Mistress looked straight into my eyes and asked 'where is the water, I still want a drink'. I clearly didn't have an answer and blurted out, maybe still in the car.

Mistress gave me 2 options, to go to the Car dressed like I was to get the water or let her tie me up so I couldn't hide, while she gets the water.

Of course not wanting to be seen by the 8-10 people we walked past near the car I opted to be tied up. It was dark and secluded and I shouldn't be seen.

I was told to fold the towel and put it on bench seat so I could sit on it comfortable without getting splinters -- Mistress is very caring in that way.

Once set up I was to sit down, Mistress proceeded to tie my ankles about 11/2 shoulder width apart to the bench seat legs then wrapped it up from behind my back where she made some sort of waist strap that kept me secure to the seat with the rope then proceeded to tie my forearms to my knees so my wrists and hands just hung over my knees. I was tied sitting down slightly learning forward without the ability to get my ass of the seat.

Once in place, Mistress took my lipstick and applied a lot to my lips, actually a real lot. Then with what light was available she applied eye liner and placed the wig on my head..

Mistress then stood back and took a few photos and said, tomorrow night is going to be so much fun, you are going to love it. Can you get out sissy, I struggled in the bonds but couldn't. I was stuck. I simply tried but couldn't. Mistress then grabbed her strap on dildo held it in place as if wearing it and moved towards my mouth. She was at perfect height to fit the dildo in my mouth. I opened my red sissy lipstick lips as she slowly fucked it into my mouth, Her first push was just the head of her monster cock, and then pushed the next thrust in deeper, and again as deep as she could. I could not move a lot so it went deep down my throat. Its so good to have my sissy cock sucker back in person.

She then grabbed my phone and earphones off the table, went through my Music and found the Hypnosis audios, found what she wanted and played a cock sucking hypnosis file, then put them in my ears, pulling a blindfold over my head which held the earphone in place and succeeded in removing 2 more of my senses. I could not move, I could not see anything and now I could only hear sissification cock sucking audio in my head. I felt her kiss me on the cheek lifted one of my head phones and said, 'Be a good sissy and stay here, Ill be back real soon!" then silence again.

After about 1 min, I wasn't sure if she was there or not, then my plug started to vibrate. It was low to med, the deep vibrations that Mistress new was my edging spot. I would never cum from this rhythm but it was teasing my G-Stop and I felt it deep within my pussy.

The angle I was force to sit in and being pulled onto the bench had the plug pushing hard into my sissypussy, the vibrations quiet but my moans were slightly auditable so I imagined.

Not sure if my moans were load or quiet, I could feel the vibrations of my plug as if I could hear them and the sound of the audio, "You are a cock sucker, you need to suck hard cock and want cock all the time. A cock sucker can't live without cock. You need to suck cock, you want to suck cock, you must suck cock, a lot of cock any cock. Say I am a cock slut, I am a cock slut". The words and music continued and my pussy vibrated, time felt slowed and I was unsure how long I was here for. The majority of the hypnosis files go for about 40min and I was truly getting into it, I started to say word, I quietly called out, I need cock, I am a cock sucker as I could feel my clitty leaking sissy fluid.

Was it 10min, was it 20min, I was not sure. Mistress should be back I tried to listern and sense if anyone was there, the Audio continued and never went silent so It was no luck..

Was I alone??

My senses starting playing up, "is someone there? Hello" I called out.. more time passed, I tried my bonds and still to no luck. Did someone just touch me. Hello I called out again.

Mistress is that you? I felt a hand touch me, then it stopped.. then I felt it again..

I winched in shock as my right nipple was squeezed. I felt a hand on my face, fingers running down my cheek, then touched my lips. I commented again, Mistress can I see you please?

Again a finger touched my lips, I opened my mouth and licked my Mistresses finger. She was playing with me, I sucked her finger as if it was her strapped on cock.

She was gone again, I wanted to play along as it had been so so long since I was in my Mistresses company. I spoke 'Fuck my face please' and I opened my mouth and waited.

Within seconds I felt her push her cock in my mouth again, I felt it go in deep and out then in again but what... I felt pubs on my noise, This was not Mistress and it was a real cock. It felt different, warm and flexible.

I tried to move but couldn't I had a real cock in my mouth. It was growing in my mouth with each thrust, soon it was at full length and girth as started to fuck my face, I felt his hand on the top of my head, as he started to really get into the rhythm.

I could not see what he looked like but knew his cock was smaller than my Mistress cock and I just sucked him as the words in my ears kept telling me to do. I sucked, licked and gagged on this random cock, I was getting into it, I slurped and moved my head forward with every thrust to try and get as much as I could in my throat. It wasn't long when he changed and started to tense up. His had moved to my head, where he pushed his cock in deep and held it there. At first I tried to pull back but couldn't, I know he was close to cumming and before I could mumble anything he shot his male cum deep in my throat. It was fast and over in about 4 spurts. He quickly pulled out and was gone. Here I was, still tied up just sucked off some random strangers cock that fed me his cum deep in my throat and belly and left.

I was still in shock at what just took place and was licking my lips when I felt 2 hands touch and hold the sides of my head. Think I was going to have the blind fold removed. I was wrong I had another cock pushed into my face and I opened my mouth. Something was different it was bigger and harder a lot harder. Without hesitation my face was fucked. It was like a piston driving into my mouth.. I gagged a lot and had tears welling in my eyes. He was not letting up at all and kept driving his cock deep into my mouth. When he pulled out, he turned my head and another cock was pushing into my mouth. I was sitting here tied up while 2 men took turns fucking my mouth, they changed every few minutes to stay hard. The audio in my ears ended and the next one started to play and it was at this time when I heard my Mistress say.

Ofcourse you can do that.. and without knowing what they asked the next audio started.

Their cocks were removed and I felt hot jets of cum spray onto my face, cum hitting my nose and eyes, in my mouth and all over my face. It was at this time the blind fold was removed and bright light was shining in my face, while my eyes adjusted another load of cum was sprayed across my face. Then another, and another with the last one, cumming directly into my open mouth from a distance, I made out 4 figures no 5, It was 4 men that cum on me, all over my face and clothes, cum leaking off my face onto my body stocking, as I sit there tied but, pussy vibrating and cum all over me.

When my eyes finally adjusted, I seen my Mistress standing with a camera that had a light pointing at me filming what I was doing.

As I looked at her in surprise, she just laughed and said; Welcome to your new life you sissy cock slut. Tonight is only the beginning.

Mistress then turns the camera to yourself and says, thank you all and everyone that watched this session, stay tuned for more sissification sessions with jona.

Tonight you have witnessed sissy jona receives her first every bukkake cum facial and forced cock sucking session. Thanks for watching. Mistress Jae signing off.