Hubby's First Time
I sat in the hotel room and waited. Shortly after the agreed time the door opened, and in walked Mistress leading Hubby by the hand. I stood and bobbed a curtsy.
They'd been downstairs having a romantic dinner, she dressed in a dark blouse and skirt, he in smart jacket and trousers. We exchange some pleasantries - yes, room service was good thank you. Dinner in the restaurant was lovely, the wine excellent and the service in the Country Manor as good and attentive as ever.
Mistress poured herself another drink and I asked Sir,
'You know why I'm here, Sir? To provide you and Mistress with services. I understand that she's discussed this with you?'
"Yes, we've talked and I'm looking forward to your help', he said, looking me over a little nervously.
I'd spent ages getting my makeup right, choosing my red angora cowl neck sweater and black pleated skirt, trying to look my best for Him, my steel collar clearly visible as a sign of my submission to both.
https://xhamster.com/photos/gallery/5469555/390723626
I am six foot four in my heels so I lowered myself onto my knees as Mistress brought Him a drink too. 'And you're sure you're OK with me pleasuring you, Sir?' He looked down at me; 'Yes' he said, It's what Mistress would like, and whilst I'm new to all this, it's fine'
'I'm new to playing first hand too, Sir, but I'll try and make it as enjoyable as I can for you...
'...Thank you', I said, and started to unbuckle the belt on his trousers. 'Let me help you get ready. I'll take off your trousers and pants and I'd like you to sit over there in the chair' He took off his jacket as I slid his trousers to the floor and undid his shoes. He kicked them off and I looked up. His shirt tails covered his pants, thankfully there was a bulge starting to form already. Mistress Sarah was behind me and to one side, watching proceedings with interest, head tilted slightly as I gently felt his bulge growing through the fabric. I put my face close to him
'Would you mind unbuttoning your shirt too please' I said as I gently kissed and nuzzled his growing excitement. As he undid his shirt I stood and slipped the sleeves off his shoulders but didn't let his arms out altogether. Gently rubbing my fluffy breasts against his chest I lead him to the chair and sat him down - the shirt holding his arms in place by his side, I guided his pants down as he sat, to be rewarded by his semi erect penis swaying from side to side, right in front of my face as he sat.
'I hope you don't mind a little restraint, Sir. I don't want any help or interruptions once we start'. His arms were by his side, held in place by the shirt around his back and underneath him. I gently opened his legs and knelt between them, my full fluffy breasts caressing the inside of his thighs, deliberately so - I know how soft and sensual angora can feel there - I hoped it was having the same effect on him as it was on me - I was attempting to get hard inside my tiny cage and knew it would not be long before my lacy panties would be damp with my own excitement.
I leaned in and kissed the tip of his penis, gently licking the end whilst I held the shaft in my left hand, squeezing gently. With my right I gently rolled down his foreskin, the penis head and glans smooth and shiny in front of me. He was partly (mostly) shaved.
'I love how you have a little landing strip, Sir' He looked at me. I continued 'It's such a lovely sign of your relationship with Mistress. Your secret with her, a sign of Her gently imposing Her will...' I gently stroked it, feeling the short stubbly pubes, and the smoothness either side. In my mind some men are trimmed, some completely shaved (particularly if chastity devices are involved) but a landing strip is a very feminine style - I'd tried and failed to make an effective one myself - my hair too fair to make a decent impression. At this point the temptation to lower my lipstick lips around the head of his penis was strong, but penetration had not been allowed by Mistress, so I gently breathed on the tip as my soft hands went to work.
I gently stroked his strip as I continued to massage his shaft with my left hand then cupped his balls with my right, rolling them between my fingers. He was still growing, sticking straight up - the hardening shaft and head still as I moved his foreskin up and down gently.
I stood up on my knees slightly and pressed him between my fluffy breasts, the large oversized cowl covering his head as I squeezed my breasts around him. I rubbed them up and down his shaft and moved the cowl out of the way with my chin to see his shiny head poking through the soft fluffy fabric of my sweater. I kissed it again and sat back down on my heels.
I reached down and picked up a small bottle of essential oil, lavender, and poured a little over his domed penis head. It ran down in little rivulets to my hand where I rotated it and gently massaged it into his penis - now sliding my hand up and down the slick skin, over the head, back down - feeling the veins and ridge of the head ripple under my fingers as I gently masturbated him. He shuffled his bum forward; he was completely hard by now, I could feel his pulse deep inside the shaft. I let go - it glistened as it stood in front of me gently moving as he breathed, pulsing slightly as he maintained his hardness. It was a good size, around 8 inches - slightly bigger than mine used to be.
I took it in both hands, fingers interlocked on his side, my polished nails also shining in the lavender oil. I gently rubbed my thumbs under his glans - softy circular one up one down, together, concentrating on massaging his most sensitive parts, before returning to stroking him, I kept up this cycle for some time, also massaging his smooth balls as my hand went up and down his shaft... Sometimes I would swirl my fingers over the crown of his helmet - until eventually I was rewarded with a stringy trace of precum - silvery and shining. It sat on top of his oiled skin and formed a string as I lifted it upwards.
'Are you enjoying my services, Sir ? I said as I continued to play with the precum on the very tip of his erection
It was hard to deny at this point 'Mmmyes' , he mumbled in a husky whisper, and glanced at Mistress, who was now leaning in, watching her sissy ministering to her Husband intently, hands cupping her chin, knees together as she sat on the sofa opposite.
'I'll carry on shall I?' I asked - she nodded slightly and I dripped a little more oil on him and went back to alternating between shaft rubbing and massaging his glans...
Soon he started breathing more deeply, getting closer I think. I placed one hand under his balls and massaged the area between his balls and anus gently with my oily middle finger... all the time rubbing the very tip of his crown or the underneath of his glans - now with just a single finger, gently making circular motions like a lady rubbing her clitoris... quicker then slower as more precum appeared on the tip. His chest was heaving at this point and I stopped altogether - his fully erect, slick engorged phallus right in front of my face... twitching at the point just before orgasm... more precum oozed from the tip a little faster than before, I let it run down his shaft this time to add to the oil. Softly I started stroking him again, again pressuring his prostate behind his balls. He tried to move his hands up but they were still restrained by his shirt. I stopped again and was rewarded as his precum turned creamier and ran in a stream down his penis... I caught it with my hand to form a little pool. I turned to Mistress Sarah
'He's cumming Mistress, but hasn't orgasmed yet - you do want him to orgasm don't you?' She tipped her head slightly to affirm and as the flow of cum stopped, I paused... for two or three minutes before I went back to stroking him. He looked at me past his glistening penis - eyes telling me to get on with it. I looked, slight smile on my lips, my hands poised ready.... but poised they stayed - teasing him, paying with the pool of precious cum cupped in my palm with the fingers of my other hand....
Then back to rubbing his cum into his penis, now I released my hand from underneath him, my polished fingertip circling the very top of his helmet as I pumped his shaft - still with very soft hands but quicker now. The cummy oily mixture making a delicious sloppy, classic, unmistakable sound as I masturbated him. He started to arch his back and I moved my had quicker still, His breath became shorter and quicker, I pushed him back down as he tried to lift his buttocks from the chair, and then he came...
I continued to rub, pulling the tip of his penis towards me - not letting up the rhythm at all. I was still kneeling directly in front of him and great gouts of his cum were flying in my direction. I love cum! It splattered into my face and hair to start with then as I continued to pump him, it ran down my hands and dripped onto my black leather skirt. I kept up the rhythm - going faster if anything - into the zone where the sensation of cumming becomes intense for the cummer, he really did arch his back this time as his penis continued to pulse in my hands, the last few blobs of cum flying off the tip as I rubbed... and then, without letting go, I slowed and almost stopped. He sat back down looking ant his engorged penis, his cum covered transvestite, his wife... Mistress now had a loving smile as she looked at him. I gently ran my hand up and down his shaft one last time and released him. I love how erections sustain themselves afterwards before diminishing slowly.... His was no exception, it continued to pulse gently too as the cum and oil mixture continued to dribble onto my lap. The cum on my face also slithering from my chin onto my bright red sweater - it shows up so well on red angora! Some ran down my neck inside too - I savoured the taste on my lips and the musky unmistakable smell of fresh sperm.
https://xhamster.com/photos/gallery/5469555/390723497
'Thank You Mistress,' I said as I turned to look at her 'for allowing me to pleasure your husband - I hope you enjoyed my service'. I turned back to hubby, 'Thank you Sir, I hope you enjoyed your hand job. I enjoyed pleasuring you - including giving you a ruined orgasm before the main event. I hope you didn't mind'.
'There is one last thing for me to do before I hand you Back to Mistress.' I said as i turned back to him. 'If you will allow me...' I motioned my arm towards the bathroom door, and I led him in. I ran some warm water and soaped up my hands before once again kneeling before him, this time washing the mess of cum and oil from his now shrinking penis, balls, thighs - cum really does get everywhere. I rinsed the suds off him, again masturbating his shaft but now there was no reaction as it gently returned to it's flaccid state. I stood back up and caught the sight of my cum covered face, white goo spattered all over my breasts in thick strings, soaking into the soft fluffy fabric. Another hard to explain trip to the cleaners, except this time the cum was not mine, it was much better than that!.
I dried him, rubbed some body lotion into my palms and again kneeled in front of him. One last little kiss on the tip and I moisturised him, gently rubbing the cream into his still blushing skin, the smoothness of his balls and pubic bone, save the little black landing strip of stubble . I looked up and said 'Now I can return you to your wife, Sir . I think she may have something for you'. He led the way back into the bedroom and Mistress turned to him, holding his chastity device in her hands. He lay on the bed as gently, she slipped the ring over his penis and balls, then slid the cage gently up to make the join. Slipped the lock in and turned the key.
I curtseyed to each of them in turn, Once again expressing my thanks for being allowed into their space if only for a short while. I turned to the door and cum still running down me, returned to my own room in the far wing of the hotel to savour the experience in my own little sissyspace.
They'd been downstairs having a romantic dinner, she dressed in a dark blouse and skirt, he in smart jacket and trousers. We exchange some pleasantries - yes, room service was good thank you. Dinner in the restaurant was lovely, the wine excellent and the service in the Country Manor as good and attentive as ever.
Mistress poured herself another drink and I asked Sir,
'You know why I'm here, Sir? To provide you and Mistress with services. I understand that she's discussed this with you?'
"Yes, we've talked and I'm looking forward to your help', he said, looking me over a little nervously.
I'd spent ages getting my makeup right, choosing my red angora cowl neck sweater and black pleated skirt, trying to look my best for Him, my steel collar clearly visible as a sign of my submission to both.
https://xhamster.com/photos/gallery/5469555/390723626
I am six foot four in my heels so I lowered myself onto my knees as Mistress brought Him a drink too. 'And you're sure you're OK with me pleasuring you, Sir?' He looked down at me; 'Yes' he said, It's what Mistress would like, and whilst I'm new to all this, it's fine'
'I'm new to playing first hand too, Sir, but I'll try and make it as enjoyable as I can for you...
'...Thank you', I said, and started to unbuckle the belt on his trousers. 'Let me help you get ready. I'll take off your trousers and pants and I'd like you to sit over there in the chair' He took off his jacket as I slid his trousers to the floor and undid his shoes. He kicked them off and I looked up. His shirt tails covered his pants, thankfully there was a bulge starting to form already. Mistress Sarah was behind me and to one side, watching proceedings with interest, head tilted slightly as I gently felt his bulge growing through the fabric. I put my face close to him
'Would you mind unbuttoning your shirt too please' I said as I gently kissed and nuzzled his growing excitement. As he undid his shirt I stood and slipped the sleeves off his shoulders but didn't let his arms out altogether. Gently rubbing my fluffy breasts against his chest I lead him to the chair and sat him down - the shirt holding his arms in place by his side, I guided his pants down as he sat, to be rewarded by his semi erect penis swaying from side to side, right in front of my face as he sat.
'I hope you don't mind a little restraint, Sir. I don't want any help or interruptions once we start'. His arms were by his side, held in place by the shirt around his back and underneath him. I gently opened his legs and knelt between them, my full fluffy breasts caressing the inside of his thighs, deliberately so - I know how soft and sensual angora can feel there - I hoped it was having the same effect on him as it was on me - I was attempting to get hard inside my tiny cage and knew it would not be long before my lacy panties would be damp with my own excitement.
I leaned in and kissed the tip of his penis, gently licking the end whilst I held the shaft in my left hand, squeezing gently. With my right I gently rolled down his foreskin, the penis head and glans smooth and shiny in front of me. He was partly (mostly) shaved.
'I love how you have a little landing strip, Sir' He looked at me. I continued 'It's such a lovely sign of your relationship with Mistress. Your secret with her, a sign of Her gently imposing Her will...' I gently stroked it, feeling the short stubbly pubes, and the smoothness either side. In my mind some men are trimmed, some completely shaved (particularly if chastity devices are involved) but a landing strip is a very feminine style - I'd tried and failed to make an effective one myself - my hair too fair to make a decent impression. At this point the temptation to lower my lipstick lips around the head of his penis was strong, but penetration had not been allowed by Mistress, so I gently breathed on the tip as my soft hands went to work.
I gently stroked his strip as I continued to massage his shaft with my left hand then cupped his balls with my right, rolling them between my fingers. He was still growing, sticking straight up - the hardening shaft and head still as I moved his foreskin up and down gently.
I stood up on my knees slightly and pressed him between my fluffy breasts, the large oversized cowl covering his head as I squeezed my breasts around him. I rubbed them up and down his shaft and moved the cowl out of the way with my chin to see his shiny head poking through the soft fluffy fabric of my sweater. I kissed it again and sat back down on my heels.
I reached down and picked up a small bottle of essential oil, lavender, and poured a little over his domed penis head. It ran down in little rivulets to my hand where I rotated it and gently massaged it into his penis - now sliding my hand up and down the slick skin, over the head, back down - feeling the veins and ridge of the head ripple under my fingers as I gently masturbated him. He shuffled his bum forward; he was completely hard by now, I could feel his pulse deep inside the shaft. I let go - it glistened as it stood in front of me gently moving as he breathed, pulsing slightly as he maintained his hardness. It was a good size, around 8 inches - slightly bigger than mine used to be.
I took it in both hands, fingers interlocked on his side, my polished nails also shining in the lavender oil. I gently rubbed my thumbs under his glans - softy circular one up one down, together, concentrating on massaging his most sensitive parts, before returning to stroking him, I kept up this cycle for some time, also massaging his smooth balls as my hand went up and down his shaft... Sometimes I would swirl my fingers over the crown of his helmet - until eventually I was rewarded with a stringy trace of precum - silvery and shining. It sat on top of his oiled skin and formed a string as I lifted it upwards.
'Are you enjoying my services, Sir ? I said as I continued to play with the precum on the very tip of his erection
It was hard to deny at this point 'Mmmyes' , he mumbled in a husky whisper, and glanced at Mistress, who was now leaning in, watching her sissy ministering to her Husband intently, hands cupping her chin, knees together as she sat on the sofa opposite.
'I'll carry on shall I?' I asked - she nodded slightly and I dripped a little more oil on him and went back to alternating between shaft rubbing and massaging his glans...
Soon he started breathing more deeply, getting closer I think. I placed one hand under his balls and massaged the area between his balls and anus gently with my oily middle finger... all the time rubbing the very tip of his crown or the underneath of his glans - now with just a single finger, gently making circular motions like a lady rubbing her clitoris... quicker then slower as more precum appeared on the tip. His chest was heaving at this point and I stopped altogether - his fully erect, slick engorged phallus right in front of my face... twitching at the point just before orgasm... more precum oozed from the tip a little faster than before, I let it run down his shaft this time to add to the oil. Softly I started stroking him again, again pressuring his prostate behind his balls. He tried to move his hands up but they were still restrained by his shirt. I stopped again and was rewarded as his precum turned creamier and ran in a stream down his penis... I caught it with my hand to form a little pool. I turned to Mistress Sarah
'He's cumming Mistress, but hasn't orgasmed yet - you do want him to orgasm don't you?' She tipped her head slightly to affirm and as the flow of cum stopped, I paused... for two or three minutes before I went back to stroking him. He looked at me past his glistening penis - eyes telling me to get on with it. I looked, slight smile on my lips, my hands poised ready.... but poised they stayed - teasing him, paying with the pool of precious cum cupped in my palm with the fingers of my other hand....
Then back to rubbing his cum into his penis, now I released my hand from underneath him, my polished fingertip circling the very top of his helmet as I pumped his shaft - still with very soft hands but quicker now. The cummy oily mixture making a delicious sloppy, classic, unmistakable sound as I masturbated him. He started to arch his back and I moved my had quicker still, His breath became shorter and quicker, I pushed him back down as he tried to lift his buttocks from the chair, and then he came...
I continued to rub, pulling the tip of his penis towards me - not letting up the rhythm at all. I was still kneeling directly in front of him and great gouts of his cum were flying in my direction. I love cum! It splattered into my face and hair to start with then as I continued to pump him, it ran down my hands and dripped onto my black leather skirt. I kept up the rhythm - going faster if anything - into the zone where the sensation of cumming becomes intense for the cummer, he really did arch his back this time as his penis continued to pulse in my hands, the last few blobs of cum flying off the tip as I rubbed... and then, without letting go, I slowed and almost stopped. He sat back down looking ant his engorged penis, his cum covered transvestite, his wife... Mistress now had a loving smile as she looked at him. I gently ran my hand up and down his shaft one last time and released him. I love how erections sustain themselves afterwards before diminishing slowly.... His was no exception, it continued to pulse gently too as the cum and oil mixture continued to dribble onto my lap. The cum on my face also slithering from my chin onto my bright red sweater - it shows up so well on red angora! Some ran down my neck inside too - I savoured the taste on my lips and the musky unmistakable smell of fresh sperm.
https://xhamster.com/photos/gallery/5469555/390723497
'Thank You Mistress,' I said as I turned to look at her 'for allowing me to pleasure your husband - I hope you enjoyed my service'. I turned back to hubby, 'Thank you Sir, I hope you enjoyed your hand job. I enjoyed pleasuring you - including giving you a ruined orgasm before the main event. I hope you didn't mind'.
'There is one last thing for me to do before I hand you Back to Mistress.' I said as i turned back to him. 'If you will allow me...' I motioned my arm towards the bathroom door, and I led him in. I ran some warm water and soaped up my hands before once again kneeling before him, this time washing the mess of cum and oil from his now shrinking penis, balls, thighs - cum really does get everywhere. I rinsed the suds off him, again masturbating his shaft but now there was no reaction as it gently returned to it's flaccid state. I stood back up and caught the sight of my cum covered face, white goo spattered all over my breasts in thick strings, soaking into the soft fluffy fabric. Another hard to explain trip to the cleaners, except this time the cum was not mine, it was much better than that!.
I dried him, rubbed some body lotion into my palms and again kneeled in front of him. One last little kiss on the tip and I moisturised him, gently rubbing the cream into his still blushing skin, the smoothness of his balls and pubic bone, save the little black landing strip of stubble . I looked up and said 'Now I can return you to your wife, Sir . I think she may have something for you'. He led the way back into the bedroom and Mistress turned to him, holding his chastity device in her hands. He lay on the bed as gently, she slipped the ring over his penis and balls, then slid the cage gently up to make the join. Slipped the lock in and turned the key.
I curtseyed to each of them in turn, Once again expressing my thanks for being allowed into their space if only for a short while. I turned to the door and cum still running down me, returned to my own room in the far wing of the hotel to savour the experience in my own little sissyspace.
3 years ago
The accompanying photos a true delight to behold