Bisexual Sissy Ch. 01

I walked through the front door after a long day at work. It was an exceptionally long week and still had to go back tomorrow. I could think of nothing better than to have a shower, sit on the couch and relax with some mindless show on TV. My wife's car was in the drive, but I could not see my wife, so I headed to the shower.

As I was in the shower, the thoughts about work washed off me like soap suds. New thoughts appeared into my head. Yesterday, my wife made me clean out my anal passage with a nice warm enema. It was very sensual thinking back on it, but at the time it felt more like a punishment.

My wife had led me to the bedroom. She had asked me to get out of my work clothes and get the enema kit from the bathroom. This is not unusual apart from it was midweek, however, what my wife has planned, I was not going to say no. She asked me to fill the bag up with warm water. I enjoy it a little on the hotter side, so I had the temperature exactly right. I took it back to my wife who was waiting for me with a bottle of lube in one hand and a rubber glove on the other. I put the bag on the bedside table and gave my wife a kiss on her soft lips. She told me to lay on the bed, which I did raising my bum slightly in the air. The cold lubed finger slid into my tight but awaiting arse. The finger was removed, and the nozzle of the enema tube inserted. Warm water started to fill my insides. The first wave of wanting to expel hit, I wiggled a little and it passed. The other three came and dissipated as easily as the first. I looked at my tummy hanging down and realised I must be nearly finished. I looked up and the bag was finished. The cramps started and the feeling to expel was full on.

Right then, my wife appeared in the bathroom. 'Looks like you are enjoying your shower' Caitlin said looking down at my cock.

'It is nice in here, you should join me darling' I replied with a smirk.

'Once you are finished in there, I have laid somethings on the bed for you. I hope you have no plans for tonight Daniel?' Caitlin turned and left the bathroom.

The enema now made sense, my darling wife had plans for this evening, however I was not sure what they were and what the 'things' on the bed were. Maybe it was a new toy? My thoughts started to wonder again. I turned the water off and dried my body. My 6-inch cock was hard with the thoughts I was having and made a tent in the towel I had wrapped around me.

I went to the bedroom and stood staring at the bed. There was pink, white and frills. Lots of frills. I was a little shocked and confused. Did my wife mean she had left some things for her to wear? 'They are very cute frills sweetheart. Come here so I can help you get them on'.

Caitlin walked in. She said nothing as she grabbed a chastity cage from the bedside table. She knelt in front of me and caged up my cock. 'Hurry up and get dressed before you get too cold.' Said Caitlin sternly.

'Where are my clothes?' I asked confused.

'Yes they are your clothes Dani, its time to get dressed' Caitlin said, this time a little firmer. I continued to stand there and stare. 'Daniel, get your sissy clothes on now' my wife was very firm this time.

I have been dressed in girly knickers before in the bedroom, but never before been referred to being a sissy before. I obliged and began putting the clothes on. As I was getting dressed, I wondered about the fantasy my wife was going to play out this evening.

I began with a black frilly bra with white dots on it. Then the matching undies which was crotchless where my arse was. I did start to put her plan together. She is going to Peg me, this was something we have done multiple times. My cock began to swell again as I could feel the soft silky material of the bra and panties against my skin. The next item was a pair of white pantyhose which I pulled over my feet and then continued to pull until they went over my frilly panties which has a bulge where the plastic chastity cage was. Lastly was a pink skirt which I pulled up. This covered my undies and my caged cock.

My wife came back into the room. 'Good to see you can listen and follow orders Dani. You make a pretty sissy'. She added. 'Now twirl like a little ballarina', she ordered. I twirled an my skirt lifted. 'Wow, if I was a guy, I would be happy to find such a cute girl in my room'. I felt a little silly standing in our bedroom dressed like a girl, however, with my wife wanting to do this and me getting a pegging, I would suck it up for a little bit of time and try to enjoy the new wardrobe I was wearing.

Caitlin walked over to me and placed a ball gag in my mouth. She tightened the strap behind my head. She then reached over to the cupboard and pulled out a blindfold. 'Time to use your imagination'. My world went dark. She tied the blindfold in place. I was then led around the bedroom and pushed backwards. Thankfully, my wife had pushed me onto our bed. It was a quite different feeling being controlled when you have little control. My hands were then bound with some restraints and then ankles. I now had no control. What did my wife have in mind?

I did not have to wait long to find out. Her lips met mine and she started kissing me with passion. Her fingers found their way to my nipples. She rubbed my covered nipples and the feeling was so sensual. There was feeling, but not usual direct feeling. She began flicking my nipples through my bra. This sent my nerves shooting to my head and throughout my body. Her hands continued down my body, lightly caressing my skin toward my lower half. I could feel my skirt lift and a hand move into my pantyhose.

She did not have to go under my panties as the cut-out was perfectly placed for her to find what she was looking for. She started tapping my tight hole. She removed her hand and placed a pillow under my bum to raise it. The finger reappeared at my bum and the wet cold finger slid in. It stretched my hole and made more nerves shoot throughout my body.

I was moaning with pleasure while Caitlin was rubbing my prostate. I could feel my cock be restrained in the cage. She removed her hand from out of my stockings and skirt and ensured it all went back down neatly. My wet bum hole felt strange being allowed back to its normal state. I could hear some music start. It was some nice soft music that we enjoyed listening to while we made love, often with candles burning. Without my other senses, I was focusing on the breeze that was cool on my skin. I laid there waiting with thoughts of what was to come next. It seemed to take forever.

I felt movement on the bottom half of the bed and instantly my head began to wonder what was happening. My legs were lifted, and my stockings were ripped open. My bum cheeks were spread open and the head a rubber object pressed against my tight bum. 'How does my sissy slut like to be fucked?' asked my wife.

I just moaned against the ball gag as i could not answer. With that my wife thrust forward and a large strap on inserted my rectum. It felt huge as I had only had a finger in there previously today. I moaned against the gag with a little bit of pain. A few slower thrusts followed by faster harder ones. My wife mimicked my voice 'I like to be fucked hard in my back pussy by my wife', as she answered her own question. My cock was very tightly contained in it cage and was dripping plenty of precum.

My wife stopped fucking my arse. 'Time to roll over sissy, i need to fuck your hole harder like you want.' Caitlin rolled me over onto my front so my face was pressed into the bed and my arse high in the air. My arse felt very exposed, even though my skirt was covering my bum.

My skirt was lifted. Cold lubricant was dripped onto my warm arse. I could only guess what was now to come. Another strap on pressed against my arse, I grimaced in pain and this one was larger than the first. 'Do you enjoy cock inside you sissy?' asked my wife.

Inside I was begging to be fucked harder but without being able to say slow down, it was a little painful. All I did was nod. The new strap on was wider and longer. I wondered where my wife had been hiding this one. It made my cock nearly explode in the cage as it was going very deep. After a few slower thrusts, they become harder faster and deeper.

After the my arse started to normalise and I could take the dildo without too much pain, I noticed something different. I felt something slap my balls, another pair of balls. I was trying to think of a strap on I had come across which had realistic balls on it when my ball gag was removed. I tried to ask my wife about the strap on when my mouth was filled with another strap on.

'How do you like having a real man inside of you?' My wife asked. Only then did I realise that the strap on in my arse was actually a real cock. I tried to answer, but I could only moan while my wife had a strap on down my throat. I then focused my attention on the cock in my arse. It felt really nice, deep, wide, softer on the outside. My cock felt like it was going to break out of the cock cage, I wanted to cum, one touch would have sent me over the edge. I was bobbing up on my wife's cock in my mouth while I had the guy thrusting behind me. I was at the mercy of the guy with his pace and depth of his thrusts. The constant slapping of balls on balls was a nice reminder of what was going on back there.

Suddenly, the strap on was removed from my mouth and replaced with warm wet pussy for me to eat. 'Time for a drink sissy. Make sure you stay hydrated as we might be here all night'. I lapped at her pussy tasting all of her juices. I thought how much my wife must be enjoying this if she is this wet. The warm strap on was resting on my face and was dripping with sticky saliva.

'How did you enjoy being fucked by 2 cocks at the same time', asked Caitlin. I nodded while continue to lick her very wet pussy. The guy behind me gave a few deeper thrusts and my mouth and nose went deeper into my wife. I was covered with her sweet-scented pussy juice. She was very wet and turned on watching me get fucked. I continued licking at her clit and pussy. I heard my wife mutter oh fuck before she tensed up and came with my tongue inside her.

I was glad that my wife was so turned on for this experience. I guessed that my wife cumming also helped the guy in my arse and I could feel his thick cock get bigger, the thrusts got harder, faster, and deeper. He let out a moan as he came in my arse. I expected to feel hot cum fill my insides like my wife explains when I cum in her pussy. Maybe an arse is different for feelings, but the feeling of the cock swell she was correct about. The cock was then removed and left my arse gapped. It felt a little strange not having anything inside me, and although I had nothing in my mouth, I was speechless.

'The sissy will clean that up, he is a great cock sucker.' siad my wife. I thought quickly about what my wife had said and then realised what she meant once the guy had slid his large cock into my mouth. It felt huge compared to the strap on that had been in there just moments ago. I had never had a real cock inside of my mouth, only dildos that my wife used on me. It was such a different feeling, the cock was warm, the head of the cock was well defined and the taste of the salty cum tasted so nice. This cock had been deep inside of my arse, now it was deep in my mouth. 'make sure you clean that cock sissy' said my wife. I started sucking and using my tongue to taste the cock. The real cock made everything I had sucked before seeming inferior, and now I understood why my wife enjoyed sucking my cock.

Warm liquid dribbled in my cool gaping arse which was still high in the air. 'Sissy needs to have cum inside her if she is going to breed'. My wife was filling me with cum. The cock was taken out of my mouth just long enough for a piece of rubber to be put in there and then a ball gag replaced. 'You enjoyed the taste of the cum from the cock, make sure you clean the condom sissy.'

My head was racing, that is why it felt like another strap on in my arse and that is why I was not filled with cum. The guy was wearing a condom. The same condom that was in my mouth making me drool with the taste of salty cum filling my mouth. The warm cum in my arse felt like drinking a hot drink when you are cold. As it went deeper, the warmth disseminated. I felt so taboo having hot cum inside me, and my wife telling me to breed.

My gaping arse was filled by the smaller cock. My arse was lubed with cum and the strap on slid deep without any resistance. The guy in front of me then grabbed my body and lifted me to have me on all fours. The ball gag was removed, and wife told me to spit out the condom. I was compliant. She was getting very vigorous with her fucking when my face was covered. 'Lick that arse clean like you lick my pussy sissy' demanded my wife.

I realised that my face was covered with the guy's arse. I poked my tongue out and found a tight hole. 'Get him hard again sissy, you need to be fucked again' barked my wife. I lapped at his tight hole. I did not know what to do back here. He was smoothly shaven. I stuck my tongue into the tight hole. He moaned. I am guessing this is what he liked. I continued to penetrate his hole with my tongue and my hole was being pounded my wife.

The cock was removed from my arse and it was left once again open and gapped. It felt warm, but I could feel the cool air my used lubed hole. 'That's a good sissy. Getting that cock hard again tells me that you want to be fucked by a real cock again' said my wife. At that moment, my wife and the guy left me be. 'Don't say a word sissy' demanded my wife. I had nothing in my mouth, nothing in my arse. I was laying there in my blindfold, bra, panties, skirt, and ripped pantyhose on all fours.

My thoughts were running through my head. What was going to happen next? Another arse fucking, another mouth fucking? My cock pressed hard in the cock cage. Where had they gone? What were they doing? Were they fucking? I wanted to ask my wife, I wanted to know who the guy was. I was told one thing, to not say anything.

I heard some noise back in the room. My mouth was filled by another gag, a heavier but smaller gag this time. My body was rolled over again so I was on my back, restraints were removed from my hands and stretched up, at that moment legs were also raised and attached with cuffs to each wrist. My arms and legs were in the air. My head was still on the bed, my arse raised and spread open.

The openness was then replaced with a hard cock, I knew this time as he had no condom. It was such a different feeling having skin on skin. At least this time I was ready for him. My arse was already stretched and well lubed with his cum from earlier. 'I told you he is a good sissy. Good job for getting him so hard again. I knew you wanted him to pound you again.' All i could do was agree in my head. I wanted him back in my arse.

I felt thighs on either side of my head, the world went bright as my blindfold was lifted. 'I hope you are enjoying yourself sissy. Now it is my turn to be fucked. This is what you being fucked has done to my pussy'. I looked at her pussy, it was glistening wet and I was sure I could see a drip of juice. I wondered if he fucked her pussy while they were gone to make her this wet. I noticed the gag I had in my mouth was actually a dildo gag. There was a rubber cock coming from my mouth. Now I understood what she meant when she said it was time for her to be fucked. I tried to look to see who the stranger was, but I could not see past my wife. She ensured not being able to see by replacing the blindfold.

I could feel my wife lowering herself onto the dildo gag, I could smell her sweet pussy and the warm humidity as it got close to my nose. My wife was bouncing up and down on my face. Her juices were dripping down the gag and onto my face. The smell was intense. I wanted to take the gag off and eat her pussy clean, but I was still tied and gagged.

My wife was screaming with her third orgasm for the evening when I felt the cock swell up again in my arse and I felt a hot load of cum up my arse. I almost forgot the guy was still fucking my arse as there was no friction and it has been well stretched and lubed. The cock was removed from my loose hole and I could feel the weight remove from my mouth. My balls were aching wanting to explode and my cock was trying to grow but restricted in my cage.

The restraints were released from my ankles and wrists. I could feel someone lay beside me on the bed. My arms raised above my head and bound again. My frilly panties and pantyhose were removed, and my skirt placed back against caged cock. My ankles were then restrained again. 'I told you this sissy liked being fucked and could get you to cum twice. Good little sissy slut.' Caitlin said to the unknown man. The gag was removed. 'Clean the cock up again little sissy. Don't worry about trying to get him hard again as he is not going to fuck you again.' The cock was pressed back into my waiting mouth. I licked the cum from the softening shaft and gave him a few good sucks to ensure any cum left inside him was now in my mouth so I could savour the taste.

He removed his cock and some material pushed into my mouth. I could taste precum on them. My panties. Then the ball gag reapplied in my mouth, so my mouth was very full. The shower turned on. What about me, I was thinking. My wife said in a soft voice, 'Do not worry sissy, I am not going to fuck another man, that is only you. Only sissies fuck other guys in the house'. I was slightly relieved with her words.

I laid on the bed with my mouth full and gagged, my caged cock and my arse slightly covered by my skirt. My gapped arse was leaking some of the two loads of cum mixed with lube. I was waiting to get up and see who had fucked my arse. The shower turned off, and then no noise. The silence was broken by the front door closing. 'Now you can have your turn' said the familiar voice of my wife.

My cock was released from is prison and felt so hard. My hands and legs were released from their restraints. My ball gag was removed from my mouth and I removed the panties from my mouth. I removed my blindfold and allowed my eyes to adjust to the light. My wife laid down next to me and I rolled over and onto her. I lifted my skirt, and slid my aching cock into her wet stretched pussy. I do not think I have ever felt her pussy so wet. My cock entered easily and she was very quickly filled by my cum as I did not last very long. We laid there together with my cock still in her wet pussy. I could feel the wet mess that was in me slowly leak out.

A few minutes later she asked, 'You really enjoyed being a sissy slut to a real man, didn't you?' I nodded yes. 'It really showed', She said.

'Did you enjoy me being a sissy husband for you?' She nodded yes. 'It really showed', I said with a smile.

My wife gave me another pair of panties, these ones had a back to them. 'Put them on as we don't want any leaks.' I obliged.

'Who was the guy?' I asked as we sat up in bed.

'You will find out soon enough'. She replied. 'Lets go get a drink' Caitlin said as we stood up. As my wife was leading me from the room, I noticed that there were 2 cameras set up still recording. My cock began to ache and get hard thinking about the time I just had. 'Settle down Sissy', said my wife, 'you must document what had just happened'.

The End