Nurse Jenny Lends a Hand

By Emmcee20.


Feeling dizzy and light-headed and clearly reacting to something I’d either eaten or come in contact with, I’d taken a fall and cut my left hand quite badly. It was soon apparent that I was going to the hospital. My son delivered me to the emergency room at the hospital, and within an hour or so, I was in a bed in ER with a drip in my right arm, and blood tests are taken as they tried to figure out what it was. High temp and not really with it. Nurses came and went, taking blood pressure and temp. High temp and sweating like crazy. Finally, a doctor arrived, and I was to be put under observation, kept on the fluids, and no food.

Lying on a bed in the ER, curtains were drawn and listening to the late-night sounds of the hospital. My head began to clear a little. The sensation in my lower abdomen gradually reminded me that I had not been to the toilet in some time, and I was feeling the need to pee. I ignored it for a while, figuring I won’t be here all that long, and I’ll be able to get up and go.

Time plodded on and the need built. A couple of nurses had popped in to check on me, and, after an hour or so, one replaced the fluids bag for my drip with a fresh bag. That just made me feel the need even more, and I asked her if I could go to the toilet. She smiled sweetly and said, “I’ll ask the doctor if you are mobile.” And off she went.

Time dragged, and my need grew. I heard someone passing by and called out. Another nurse popped her head in. Again, I said, “I need to have a pee.”

“Oh, okay, I’ll get you a bottle,” and she was gone.

A bottle? What for … Oh! Now I was more nervous. What … How …? I’ve never done this before, and I don’t know if it will work, but I can’t reach my cock anyway with this drip and a hand bandaged.

The curtain opened, and an older nurse – in her 40s, I’d guess, but tall and lovely looking – stepped in with a weird what looked like paper mâché bottle in her hand and closed the curtain behind her. She came around to the side of the bed. “Hello, I’m Jenny,” she smiled. Clearly summing up the situation with the drip and bandage, she then added, “Do you need a hand with this?”

Already embarrassed and knowing it was about to get acutely more embarrassing, I nodded a yes as I muttered, “Yes, please.”

“Okay, let’s see,” she added as she pulled back the sheet that covered me in my hospital gown. She put the bottle on the bed and leaned over me to gather the gown to lift it above my waist to get it out of the way. And then she looked down at my cock in preparation to go through the standard procedure that I am sure she did several times a day, but this time she visibly paused and said, “Oh!” then looked at me and smiled.

Even on my best day, with a raging hard-on, my uncut penis is a bit under 4” when hard but on a day like this, feeling ill and needing to pee, it retreats from attention. “Okay, sweety, just spread your legs a little for me,” and she placed a hand on my inner thigh to pull them apart gently. Her hand was warm and firm, unlike my dangling digit. She maneuvered the bottle into place and tried to scoop him up into the opening, but he was too small and hung to my ball sack. She leaned over me more and again looked me in the eyes and smiled before reaching in and gently lifting my cock between her thumb and forefinger and gently stretching him forward and into the opening of the bottle as she pushed it onto my short shaft and nestled it against my balls and then let me go. He gently flopped down into the neck of the bottle. Again, she looked at me, “I am so sorry,” she smiled.

I am sure she meant for the personal nature, but my mind also added that she was sorry about how small I am. An embarrassed tingle went through me. She stood back up.

“Just put your legs together to hold it in place, and you should be fine. I’ll pop back in a couple of minutes,” and she was gone. But not far. Just outside the curtain, I heard the earlier nurse arrive.

“Oh, did you help Mr. James with the bottle?”

Nurse Jenny replied in a whisper, but, being close to the curtain, I heard, “Yes, but God, he’s sooo small!”


“Yes, tiniest, I’ve seen!” she giggled, “but it’s kind of cute too.”

I couldn’t help feeling a bit of a tingle in my loins at that comment. I don’t get many women and even fewer who find a small cock cute. I had to concentrate on peeing, but hearing them and knowing they were nearby. My nervous bladder wouldn’t release. Minutes went by, and still no flow, just a dribble or two, but I knew I needed to go.

Nurse Jenny came back in, and I felt my nerves rise. “Are you finished, Mark? Or do you need a little more time?” she smiled. The way she emphasized “little” as she smiled made me feel like I was going red. “You look a little flushed – are you okay? I’ll check your temp while I am here.”

She came over to the bed and moved up to my shoulder, and got the temp gadget that they stick in your ear from the stand. She leaned over me, her boobs in her snug uniform right in my eye line as she took my temp in my left ear. Then, she stood up and checked it, and looking down on me, said, “Mmm, still up a quite a bit. How are you doing with the bottle? It can be hard, I know.”

“Not finished yet,” I said. But, of course, her saying ‘it can be hard’ didn’t help!

“Hospitals give some people a nervous bladder being so public like this even in a cubicle – try thinking of something wet like a river or something.” But, of course, the words ‘thinking of something wet’ didn’t bring a river to mind. Rather it brought her to mind, knowing she was thinking about my ‘cute’ cock and just hoping that my fantasies might come true.

“I’ll come again soon,” she smiled and left. Her voice, her words, and her proximity all worked to get me a little hard still encased in the neck of the bottle that, like a woman’s pussy, I struggled to fill. Finally, after a while and lots of concentration on rivers, my pee began to flow and flow and flow. I realized it was hours since I’d last peed, and with fluids pumped into me, I started to wonder about how much the bottle would hold. But, I needn’t have worried.

Lying there, helpless with a bottle of warm piss attached to my dick, I waited. Not too long went by, and Jenny was back. “Hello, sorry to keep you waiting – we’ve been a little busy. How did you go?” she was beside me now, and I said, “I’m finished thanks,” and she moved to take the bottle away.

Again, her warm hand on my thigh as she pulled it away from the bottle that she held in her other hand. Then she reached in to take my cock in her thumb and finger and lifted it slightly, and started to take the bottle. To my surprise, she gently shook my cock to make the last drops fall, just as I might in the toilet if I didn’t prefer to sit down to pee. I try to avoid urinals where I have him on display to much bigger guys. The warm digits holding me like that surprised me, and I flinched, my leg bumping the bottle, which created a little wave that lapped over the end and onto my cock, balls, and sheet.

“Oh, dear!” Jenny gasped as she withdrew the bottle. “I am soo sorry! It was only a small amount, but let’s get it cleaned up.” She went into action, putting the lid on the bottle and setting it aside before getting a new bed liner and asking me to roll to one side. I did know that she was getting a full view of my balls and bum. Quickly she tucked the liner under me after taking the wet one away. “There, no damage was done. Now to clean you up a little.” She grabbed a pack of what looked to be baby wipes, placed it on the bed, and took a couple. She proceeded to clean my thighs and thatch of pubic hair. New wipes and she said, “Let’s see what we have here?” as she pulled my legs apart, and my cock was in full view. “Here we go,” she added as she wiped his length and wrapped the wipe around him to gently stroke and clean the pee away. I got hard in her hand, and she looked into my eyes and smiled as she stroked a little more.

“Oh, he’s so sweet – he must be, what? Something over 3 inches?” she said, stretching her index finger to compare the lack of length. She squeezed and pulled the foreskin back tight on my shaft to make the pink head bulge, and she ran a finger along the underside sensitive ridge as she pulled forward, and the gathering skin trapped her finger. She stroked me a few times more before she stopped.

More wipes as she released him briefly, only to take him in her hand and hold him up so that she could clean my balls of any residual piss. She stroked me more as she fondled and squeezed my balls. Her index finger extended to the sensitive strip of skin behind my balls that led to my backdoor hole, her fingernail scratching its way closer while she clenched my balls in her hand. I gasped at the pleasurable pain, and there was a bigger smile on her face as she stroked me faster and squeezed me tighter. Soon she was pumping my little cock with her thumb and two fingers encasing him as she stroked and pulled the foreskin back to the painful pealing point. Too small to wrap more fingers around and still stroke its full length, she pumped into my balls harder.

“Oooh, you like that tight feeling in my hand with your little pee-pee, don’t you, Mark?” And, not too surprisingly, I came in her hand. A few little spurts of cum. “Aww, he’s so cute, Mark. Your little man was excited by me washing him.” I was as embarrassed as I could be. She continued to stroke and gathered my cum in the wipes. She kept stroking until he was empty and began to wilt.

“Oh, dear Mark, he is so small again. So tiny, he almost disappears into your balls. He’s such a cute little clitty he should be kept in some nice panties.” I winced a little at the comment, and she saw the reaction on my face to this last remark. “Do you wear panties, Mark? Pretty lace sissy panties, perhaps? I would love to see you in them!”

I was scarlet with my embarrassment, and Jenny was clearly enjoying her role. Cleaning up the mess, she smiled and said, “You take care now, and I will come back to see you later. Or I might tell one of my friends to pop in, okay?” And she was gone, but the tension was high. And I started to wonder if it was me who had spilled the pee, or she had done it on purpose?

Other nurses came and went – more BP and temp checks, a new drip bag. After some time, the need to pee arose again. After my first experience earlier, I was unsure of what to expect. I hadn’t seen the lovely Jenny again, but a few of the other faces were familiar. Again, need outweighing embarrassment and, when the next nurse came in, I told her I needed to pee. She smiled and said she’d be back with a bottle. I was not sure, but she sounded like she could have been the other nurse who Jenny told me was small. I was right.

She came back, and I saw her name was Leonie. She came around to the side of the bed – the same routine. They pulled back the sheet, then turned to the shelf, got a pair of gloves, and put them on. It was the first time I realized that Jenny hadn’t done that. She turned back and pulled up my gown.

“Jenny mentioned you’d need a hand. Please spread your legs a little, Mr. James,” and her hand was on my thigh to pull it aside. She was a lot shorter than Jenny and had to lean over me. She seemed to take a long time looking at me down there, and my fantasy brain again took over, and I felt myself stiffen a little at the thought of her face so close to my crotch and a gloved hand nearby. She glanced up at me and smiled, obviously seeing his little growth. She placed the bottle, and it a little harder. I slipped in without issue … unfortunately! “There you go,” she said with a smile, “ready for you to let the fluids go. Give me a call if you need a hand.”

The smile and twinkle in her eye told me Jenny had shared the whole story with her.

Again, the pressure to perform was on, and about ten minutes went by before I had finished and was ready to have it taken away and see whatever else Leonie had in mind. She was back shortly after, and I was stiffening in anticipation. She pulled back the cover and was just about to remove the bottle when the curtain parted, and the doctor came in. He stopped and waited while she efficiently removed the bottle and covered me again, leaving with a smile but a disappointed look in her eyes.

“Hello, Mr. James, I’m Dr. Phillips. I’ve been looking at your results. Unfortunately, you have a low-grade infection that is keeping your temp up. We’re going to get you onto some antibiotics and move you into a ward to keep an eye on you. We’ll take some more blood tests tomorrow afternoon, so you’ll be with us a little longer. Any questions?”

“I’m feeling a bit hungry and thirsty. Any chance of something?”

“We’ll be able to give you water, but we’d rather keep you fasting in case we decide to go looking inside your gut for the cause. Ice chips are fine – a little water is okay, too, but not too much. I’ll let the nurses know, and they’ll get you settled upstairs. Take care.” And he was gone.


About an hour later, I was in a private room on the 4th floor. Finally, getting something back from the medical insurance I pay top dollar for. Again, the attentive nurses were lovely, and I was ensconced in my room. Since arriving, it must have been about six hours, so it was about 4 in the morning. It was quiet, and I slept … and dreamed!

Visions of Nurse Jenny came to mind very easily in all sorts of situations where she took advantage of her power over me, having humiliated me for my small cock and talking about me being her sissy. But, unfortunately, dreams and reality can blur, so it was quite late when I woke the next morning. I felt disorientated but knew that I needed to pee. A couple of nurses came to the door to chat about me – a shift changes hand over, I soon realized. As they finished, I mentioned the need and got an “I’ll be right back with a bottle for you” from the cute young blonde.

Minutes went by, and still, no one came. My need was growing. I was ready to press the call button when I heard footsteps at my doorway. I looked over, and there was Nurse Jenny, smiling at me as she said, “I got a call from my friend up here to say you needed help to pee again. I’d finished my shift but thought I would lend a hand!” and she entered and closed the door behind her and dropped her bag on a chair. “How do you feel today? Any stronger? That little pee-pee clitty of yours needs some exercise? Come on then – let’s take him into your bathroom?”

Surprised at all of this, my cock was straining, but my bladder was aching for release. Go to the toilet? I’m supposed to be in bed – the thought of the bottle was quite attractive. “Come on, up, you both get!” she asserted, and she was beside me at the bed and tossing back the bed cover. My gown was mildly tented, and Jenny looked down and smiled as she brushed her hand across my little morning chip off the old block – I could hardly call it wood.

Dragging the drip bag stand across, she said, “Come on, into the bathroom.” So, I swung my legs over to her, and she assisted me in standing up and then steered me to the bathroom while wheeling the stand. Once inside, she said, “Okay, let me help you.” The gown was slipped down off my arm, and the Velcro tabs were undone on the drip arm so that it fell away, and I was standing naked in front of her. She knelt beside me, reached out, and fondled my growing cock as she pulled me toward the toilet and then lifted the seat. It was hard but also busting to go. “Here you go, sweety, let your little pee-pee flow while I watch. It is so cute and pretty to see my girl’s clitty all wet like that when you pee.” Her teasing tone was tying my innards in knots of humiliation, desire, and need, and I didn’t know which one was winning and unraveling first.

“Come on, Mary, let me see you pee.” The girly name just added to the torment. “Here, I will help you,” and Jenny reached out and grasped my hard cock in her warm hand and pointed it down to the toilet, “Come on, Mary, do a wee for me.”

I struggled to get it to flow, but I was also busting. I was as hard as I have ever remembered but felt the fluid strain to flow. “I think I feel something starting, Mary. Come on, let me see.”

I was speechless but reveling in every word Jenny spoke. And I felt the flow start, just a bare trickle.

Jenny stripped back my foreskin, so the bulbous head was showing, and a few drops of pee emanated from my slit and dribbled into the toilet bowl. “Good girl. More now, come on, we can’t be here all day.”

A brief splash and then a slow trickle, and I felt the flood gates were about to open when Jenny clamped her grip on my shaft tight and reached around to squeeze my balls in her warm wet hands. The pressure on the shaft and balls made me cry out as I half fell against the wall, relieved that there was a rail to catch to hold myself up, and all flow ceased. Why was her hand wet?

“Good girl, we don’t want it all wasted at once, do we. Your clitty needs to grow again and flow for me. She released my balls, and I soon realized that her hand had gone back under her uniform, and she was playing with her pussy. This play turned her on! Gently stroking my cock, I could feel her rocking motion against my leg as she fingered herself.

“Come on, Mary, more wee, please.”

And my flow built again, and she allowed a short spurt to escape before clamping me closed again, and her other wet hand was on my balls taking my breath away except now one digit was nibbling with a nail at my rear hole, which tingled to the touch.

And we repeated the cycle, only this time the wet digit pushed into me just a little, and I felt myself spasm and clench my sphincter. “Oh my! Sweet Mary likes to have her hole filled too! Lovely girl! More pee, please!” and her grip released, but the digit stayed in place and pushed forward. I felt an involuntary desire to push back on the invading finger, and my pee flowed again. Jenny allowed a steady stream to cascade into the toilet before she slightly increased her grip on my little clitty and then pushed what I now knew was a cunt juice slickened thumb into my bum. I almost came on the spot, except that I was still peeing through a rock-hard little cock.

I’d never felt sensations like this before. Pee was just pee until yesterday when I met Nurse Jenny. My back door was not a play area until now.

My piss flowed while she pumped in and out of my bum and kept my penis in her fingers. My pee trickled to an end, but I was still hard. Jenny then added, “Well done, my little pissy sissy. Time to clean you up again, I think.” Still, with a digit buried in my, she leaned forward from her kneeling position and slipped my cock into her mouth. It was hot and wet and sucked firmly on my little shaft while her tongue did laps around the crowned head. She broke free briefly to say, “You have a yummy pissy clitty Mary!” and she took me back in her mouth, bobbing her head in short motions as she took my short shaft into her mouth – it wouldn’t reach her throat.

I knew this wasn’t going to last long, and that was fine, but the final surprise that tipped me over the edge was when she pushed forward more and took my entire cock in her mouth, and her fingers scooped my balls up, and she sucked one in as well. My ring pumping continued, and I exploded in her mouth uncontrollably. She just kept up the suction, swallowing my meager seed supply. It was little time at all before my wilted and shrinking cock plopped from her lips, and she leaned back, letting her thumb pop out of my backside.

And she looked at my dwindling manhood and tickled my balls one more time as she repeated last night’s comment, “Oh dear Mark, he is so small again. So tiny, he almost disappears into your balls. He’s such a cute little clitty.”

Quickly she was on her feet and washing her hands – notably not rinsing her mouth; she had swallowed my offering whole. “Come along, Mary. Back to bed.” And she put my gown back on me and steered me out of the bathroom and into bed. Then she opened her bag.

“I have a couple of gifts for my sweet girl. Something she can keep to remember me by. I have made sure the nurse on the call knows I am giving you these gifts, so don’t worry. You can decide what you want to do with them when you go home this afternoon.”

With that, she pulled out a small, pink, quite slim (about thumb-sized) butt plug and some lube. She spread some lube on the tip and turned to me. “Come on, my sissy, spread your pussy for me.”

I spread my legs at her demand. Again, it was an involuntary response to the plunging pleasure I’d felt a while ago – again, a new experience for me. Jenny placed it at my sphincter that still felt stretched and, with, “Here you go, my girl. My little cock that is about as big as your little cock,” she slipped it into me. It filled and stretched me a little more, and then I realized that it had a neck that sort of held it in place. It was a delicious sensation. And then she bent down, and I realized she was reaching under her uniform and removing her panties. She took them off and stood to hold them for my perusal. They were pretty nylon briefs in a pale blue with cute lace around the top and legs, and they had a definite wet spot in the crotch.

“These are for you, sweety. Your little clitty will look and feel so nice in the lace. Feet up, Mary.” And she dressed me in her panties. “The last present is this,” and she took my hand and fed it under her hem and up to her soaking wet pussy. The heat was amazing, and I started to harden again as she pushed me closer, and I slipped two fingers inside her wet lips. She jerked off with my hand, her holding my wrist as she plunged me inside a few times before pulling me out and steering my soaked fingers to my mouth. I opened eagerly and suckled her juices.

She released my hand and grabbed her bag, passing me one final gift of a piece of paper with her phone number on it. “Call me sometime, Mary, when you feel better. We could have a lot of fun! Bye.” And she was gone.

I was barely back in bed and covered when the door opened with the cute blonde there saying with a big grin towards me, “Here you go, Mr. James is free now the nurse has finished,” and in came my family to visit.

The cute blonde nurse disappeared as the family traipsed into my room—lots of concern and loving care as they asked how I was and what the doctor had said. I dutifully gave them a very edited report of my hospital experience. They certainly didn’t need to know about the extra special care Nurse Jenny had given me. While they were there, a doctor popped in to say that the tests would be back soon to confirm that the antibiotics were doing their thing, so I should be expecting to go home later that afternoon.

After an hour or so of the usual uncomfortable long pauses of not knowing what to say, the family said their goodbyes and arranged who would pick me up that afternoon, and they were gone.

A short while later and the blonde nurse, Leonie, was back. “Is everything okay, Mr. James? Jenny said to make sure I gave you a hand with anything you need.”

Her emphasis on the word ‘anything’ had a clear meaning. The baton had been passed on to the next shift (though a rather diminutive baton it might be, so to speak). Having peed and cum earlier, that post-orgasm need-to-pee had built up, and I couldn’t resist her offer, so I said that I think I needed to use the toilet again. “Would you prefer a bottle? We keep a record of how much you pass.”

I paused briefly and then nodded a yes. “I’ll be back soon,” she smiled.

True to her word, I soon heard movement at the door. My fantasy brain had been hard at work, knowing that Nurse Jenny had made sure that Nurse Leonie knew all about me. My surprise must have shown as Nurse Leonie entered with two interns. Their name badges read Tegan and Sarah. They looked cute but surely were barely out of their teens.

“Hi Mr. James,” she smiled, “I hope you don’t mind, but we have some first-year trainees on the ward, so I thought they would benefit from seeing one of the regular tasks we do. Do you mind?”

I had three women looking at me and didn’t think saying no was an option. I nodded assent and tried to smile. “Okay, ladies, come and join us; pop around to the other side so you can see everything clearly.”

They moved in, and I was lying in bed, surrounded by two cute young nurses and the lovely Leonie.

“Okay, Mr. James has kindly said we could use him for our little training exercise.” As she said this, she was dropping the pee bottle on the bed and snapping on her rubber gloves. “We often need to help patients who are not mobile and need to pee – that was Mr. James because of his drip and his injury… do you mind if I call you Mark?”

She’d turned to me briefly. I muttered okay but was busy watching the two trainees, both cute but looking nervous.

“Okay, thanks, Mark. Mark has a bit of an unusual problem that can make this task rather difficult,” she commented rather matter-of-factly, as she pulled my sheet back so that my legs were exposed, and then it dawned on me that my gown barely covered me or the panties that Nurse Jenny had dressed me in.

“Usually, you can just slip the bottle onto the penis and leave it for the patient to do his business, but, as you will see, Mark is a difficult case as his cock is soooo small!”

Again, this comment stung my ears as the gown was lifted to expose me to the two girls. They giggled at the lacy panties and the small bulge my cock made in them. I hadn’t thought of this and gasped as they all leaned in to look at my lace-clad little member.

“So, you need to show respect and politely ask him to spread his legs and definitely try not to laugh at how small it is. Can you spread your legs, please, Mark?”

She reached in and pulled the panty leg aside to release my cock and then took my shriveled member between thumb and forefinger and brought the bottle to thread him in. I didn’t think he could shrink more! “Now make sure. However, little shaft there is that you can fit it into the neck as, otherwise, you’ll get a spill.” All the while, she was acting on her statements as she fed me into the bottle. “Then you let him do his business. Come on, Marky, can you do a little wee-wee for me?”

The two trainees were leaning in and stifling a giggle as they took in the lack of size. I wondered if they had ever seen one smaller. The baby talk heightened the embarrassment as I took in the idea of these nurses talking about me in panties and my small cock to whomever they might on the ward. I know I was scarlet, and my bladder suddenly felt empty. But they just stayed there talking about nursing. I closed my eyes to remove them, but that didn’t really help as I heard Leonie talking.

“Some patients get nervous and really struggle to release, but Nurse Jenny told me that Marky here doesn’t mind being given a hand to get things going.”

Suddenly the warmth of her hand was on my thigh and slipping up to my crotch. “Sarah, just hold the bottle in place,” and I felt her thumb and index finger wrap around the top of my shaft and balls, capturing them in one hand. “Being so small, his little pee-pee might fall out.”

She squeezed, and I felt him get harder, and the bottle slid back and forth as if I was fucking it. Each inward stroke put pressure on my balls but not touching the sides with my shaft. Finally, I spread my legs wide to give more access.

My hand was taken in a warm grasp, and I realized that Tegan was holding it. She pulled on it, and soon my eyes were open as I knew she was taking my hand to her crotch. I could feel her heat as she thrust onto my fingers, and I tried to wriggle them inside her. The crisp cotton of her uniform seemed to slip away, and I felt the heat of her pussy as she pulled me into her. Her thin panties had slid aside as she guided me to her lower lips, and soon the heat of her pussy devoured my fingers, and I tried to use my thumb to rotate on her clit. The constant stroking of my shaft had me hard, and Leonie’s voice crept into my consciousness.

“Oh, look … he’s got hard. It is so cute! Goodness, almost four inches, I’d say!”

The bottle had apparently gone, and I felt the firm grip stroking me and then the wet heat of a set of lips as he disappeared into Sarah’s mouth.

“You have to suck hard, Sarah, to get anything out of such a little clitty, but Mary likes her balls squeezed,” and she acted on her words, taking my balls in her other hand and crushing them in a grip I couldn’t believe was possible.

It sent a chill through me and took my breath away, but the pleasurable pain was too much, and I immediately squirted into Sarah’s mouth.

“OH!” she said and giggled, pulling back, “he’s cum so easily, and there isn’t enough cream to make a coffee. Is that all he has?”

My tiny eruption didn’t dribble down her chin like in pornos, but I was spent and seeing stars. Tegan was still rocking onto a couple of my fingers, and my hand was wet with her juices, and I felt her grip me as she moaned and then pulled away. Then, finally, I came back to Earth and looked up into their smiling faces.

“Yes, ladies,” Leonie said, “It isn’t always as straightforward as it may seem, but we try to assist our patients as best we can.”

Sarah busied herself, wiping me clean and popping me back into my panties, and then, patting my little shrunken button, she pulled up the sheet. Leonie then turned to me and added, “Jenny said to make sure you remembered to use all the gifts she gave you as soon as you can.”

She smiled, and the three ladies were gone, and soon I felt the real need to pee but quietly made my way into the toilet and finished the task. Shortly after that, yet another doctor came in to tell me that my results were all getting back to normal, and I would be discharged very soon, and that I could get dressed.

It wasn’t long, and I was in a wheelchair passing the nurse’s station where I got a cheery but professional, “Bye Mr. James,” from Sarah as she brushed something from her lip with her little finger, which she then wagged at me (the universal sign for a small cock), and then it was down to the departures where I was given a simple lunch and signed my discharge papers.

My lift arrived, and I was on my way home. A couple of recuperation days passed, and I was feeling a lot better. However, every waking moment, and most dreaming ones, was filled with thoughts of Jenny and the gifts she gave me. My brain told me that I would be humiliated by her and that she would do whatever she wanted … and my fantasy brain said that was just perfect!


After a couple of days of sick leave and got me to the weekend, I decided to make the call. I dialed the number. My nerves were jangling as I tried to figure out what to say when she answered. The phone rang and rang. I was sure she would be at work or not available and was just about to hang up when I heard, “Hi, this is Jenny.”

The lump in my throat was about the same size as the one in my pants, and my voice came out as a bit of a nervous whisper, “Hi, Jenny, this is Mark … um, Mary … I met you at the hospital early this week.”

“Oh, Mary! How are you feeling, dear? All better?” She was so cheery and warm.

“Yes, much better, thanks. I just wanted to thank you for your help.” I was sooo nervous.

“No, you didn’t;” I could hear the cool laughter in her voice, “you wanted to thank me for the presents I gave you and to see me again, didn’t you?”

Her directness caught me off guard, but she was right. Although, before I could answer, she started with a series of rhetorical questions. She already had all the answers.

“You enjoyed my presents, didn’t you? Especially my panties? They were still so warm when I put them on you. You sniffed them to remember my scent, didn’t you? You have been wearing them a lot since I last saw you. In fact, you are wearing them, now, aren’t you?”

There was a pause, and I knew she wanted to hear me say the words, “Yes, Jenny, they are lovely and feel so nice.”

“Is Mary’s little clitty a bit hard as she feels that soft material?”

“Yes, Jenny,” I murmured.

“It’s okay, Mary. Are you stroking your little pee-pee while we chat?” She knew I would be. “And do you have the cute little plugin your boi pussy?”

Her voice was teasing and demanding at the same time, but I managed to eke out the words. “I’m touching it, but I don’t have the dildo … in me.”

“Oh, dear, how disappointing! Of course, that’s not a dildo, silly. It’s a butt plug – my dildoes are much bigger than that,” her tone was playful but firm. “Stop touching yourself and go and get the plug and slip it in, then come back to the phone; I’ll wait!”

I knew she meant it, so it was another, “Yes Jenny,” and the phone was down as I rushed to my bedside table where I had kept her gifts.

Slipping her panties down, my cock sprung up to attention as I lubed the slightly larger plastic cock and bent to slip it inside me. It was smooth, and I felt little resistance, but I had already practiced this a few times this week. Once into its base, my sphincter gripped the little neck, and a warm glow grew inside me as I slipped her panties up over my hardon and dashed back to the phone.

As soon as I picked it up, I heard her, “Good girl … and so quick too,” she giggled. “Does that feel better?”


“Good, now I want you to start stroking your cute little cock through my panties and make it cum in them; start stroking my girl … just thumb and one finger. But, of course, that is about all it takes with your cute little button, isn’t that right?”

“Yes, Jenny,” I gasped as I was stroking.

“You can call me Nurse Jenny because I am here to make you feel better. Does stroking yourself through my panties make you think about what my pussy would be like Mary? Keep stroking! I could tell you if you asked nicely?”

“Please, Nurse Jenny, tell me about your pussy,” I managed to stammer as my stroking pace increased and the soft material clung to the damp head of my cock.

“Good girl, for the asking so nicely. My pussy has a nice triangle of trimmed brown hair just above the shaven lips. My pussy lips are thick, fat, and juicy that I love to have French kissed by an attentive partner who knows how to use a tongue. My clit stands up like your little cock when you have cum. Of course, your little pee-pee could slip between my pussy lips, and it would look just like a hotdog with the thin little sausage wrapped in soft, warm wet…”

“Ugghhh! Oh, God!”

I came listening to her description, her voice dripping sex as she gave details of all I had dreamed about for days. Nurse Jenny was totally in my head.

“Ahh, good girl! Keep stroking until you are empty. Did you make my panties nice and creamy? I hope so because I want to see them later, so don’t take them off. Go and get dressed, and I will text you my address. You can meet me in one hour; don’t be late!”

And she was gone! My cock softened in the wet panties, and I wiped my fingers on the lacy trim. My after-orgasm brain started to kick in; what was I getting myself into? I didn’t care; after all she had already done, I had to see her pussy and whatever humiliation she put me through, I was sure it would be worth it. On later reflection, I am not so sure, but that was several hours earlier.

Only a few seconds went by, and my phone beeped the arrival of a text. A glance said it was about a twenty-minute drive, so I had better get moving. True to her words, I didn’t change, just throwing on some slacks and a shirt and slip-on boat shoes. I grabbed my keys, wallet, and phone and headed to the car. How I got there in one piece, I don’t know, as I was daydreaming the whole time, all the possible fantasies I had ever considered could be coming true. I struggled to bring Nurse Jenny’s face back from memory, although her crisp uniform and casually direct manner were obvious in my mind.


I was soon at the address, an inner suburban home with a smart, older look and well-trimmed gardens. It seemed to suit her. I pulled into the drive and was just getting out of the car when I heard her voice, “Hello Mary, don’t come in, we need to go shopping first.”

I looked up in the direction of her voice and saw the lovely tall Jenny, only not the Nurse Jenny I met in the hospital. This was Hot Jenny walking down the path in tight black pants that showed off her long legs and a sexy semi-see-through blouse in light blue. Her nipples stood dark and erect on her ample breasts as they bounced, unencumbered by a bra, with every step she took toward me. The four-inch heels, and a glimpse of stocking, completed the vision of loveliness, and it must have shown in my expression.

“Come along, Mary, mouth closed, and door open!”

The teasing humor in her voice was music, but it brought me back as I ran around to open the passenger door for her. She stopped beside me and reached out to touch my arm as she leaned in and placed a soft, warm kiss on my cheek.

“Nice to see you again. Come on, let’s go.”

She was soon in the car, and I was reversing.

“Umm, where to?” I asked.

“Don’t worry. I’ll tell you the way. Just head back to the main road.” A brief pause as I left her street and then, with her hand finding my thigh, “Are my panties comfy or a bit sticky and wet?” Her hand crept to my crotch, so I knew which pair of her panties she was asking about. I just went red-faced; “Aww, that’s so cute, you’re embarrassed … but you are here, so I think you rather like it, don’t you?”

Her hand was caressing my crotch as I mumbled, “Yes, very much.”

“Good because we’re going to have some fun!” I couldn’t imagine what would happen, but I was rising to the challenge, and she noticed. “Oh good, there he is.”

She smiled as she fondled. She sat back, lithe and sexy, and her pants showed the faint outline of suspender clips on her thigh. My mind drew pictures. Her hand just stayed there, gently owning my cock as she gave directions, and we pulled into a small shopping center about ten minutes later and got out of the car.

“Come along. We just need a few things,” and she took my hand and led me into the mall.

It was clearly upmarket and had all sorts of boutiques all clustered. So we walked, and I followed in her wake, picking up on the wonderful perfume she was wearing and thinking how passers-by would see me as the luckiest guy around with this gorgeous woman.

“Here we are,” she smiled as she turned to look at me and pulled me into a shop.

The front window simply had ‘Close to You’ in a stylish font. We walked in, and I quickly realized this was a very chic lingerie store. Jenny must have felt my hesitation as she looked around at me.

“Come along, silly. They don’t bite … well unless you really want them to.” She smiled and pulled me forward.

It was a decent size store with only a few customers browsing, and another attractive 40ish woman was at the counter. She recognized Jenny immediately and came straight to us.

“Jenny! How are you? So good to see you,” and they hugged.

“Hi, Sue, doing well, thanks. I just popped in for a couple of things.”

It was then that Sue’s lovely face turned in my direction, “And who is this?”

She looked me up and down in appraisal. It was uncomfortable; at least I thought so until I heard Jenny’s next comment.

“Oh, silly me. This is Mary; she’s my new sissy, and she needs a bra and panties set.”

I gasped at the words and how loudly they were said and that I was only referred to in female gender, but Sue just smiled and watched me, now professionally assessing me.

“I’m not sure of the bra, but she likes my panties size. She’s still wearing them from this morning.”

I didn’t know where to hide, and, scanning the store, I noticed a couple of elegant women either just smiling or taking a direct interest in our conversation.

Sue said, “Hmm, she looks a little flushed, Jen. Let’s take her to the fitting room.”

And I was guided and towed to the back of the store, passing one of the customers who made eye contact with me and gave a knowing smile; through the racks of lovely looking apparel, we went to a curtained area. Moving in and Sue closed the curtain behind us, and then she was all business.

“So, Mary, have you been fitted for a bra before? Do you know your size?” Sue asks.

I had no answer – curiosity had meant that I’d tried some lingerie as a teen but not much since. I had tried panties and loved how they felt, but any bras I could get my hands on were all too big. So I just shook my head. I’m not in top shape but not fat, though I have always had a bit of man-boob that seemed to run in my family. I was teased as a kid at school and home by brothers because I had sensitive nipples, which girlfriends and my ex used to have fun playing with and always got me hard; we’d had fun with panties, but it had never been a big thing for me to wear a bra and I certainly hadn’t thought about getting a bra fitting.

“Mary could be a B cup Sue. I saw her at work,” Jenny said.

“Well, I will measure it anyway. Pop your shirt off, please, Mary,” Sue added. I was in stunned silence. “Perhaps she’s a little nervous? Is this your first fitting, dear?” She smiled at me. Again, I could only nod. “How about a glass of wine to relax while we sort things out for you? Andrea?”

She had called the name over her shoulder, and from the rear of the store, a younger version of Sue walked in with a small tray and a couple of glasses of champagne. Again, buxom and beautiful and about 25, she smiled at me as she offered the tray. Then, she casually glanced over to Jenny.

“Hi Jen, you’ve brought someone new for us to help. Thanks,” Andrea said.

“Hi Andrea, yes, this is Mary, my new sissy,” Jenny said as she took the glasses and gave me one. I took a large gulp. “This is all pretty new to her, so I thought we’d start with some nice lingerie.”

“Good idea.” Andrea turned to me, “You’ll look and feel wonderful, Mary, I promise. But, I’d better get back out into the store. See you both later.” And she was gone.

A few sips more of the champers, and I started to feel the bubbles do their thing. It crossed my mind to wonder what Jenny meant by ‘we’d start with some nice lingerie.’ I hadn’t realized, but Sue had busied herself while Andrea was there and now had a tape and notebook at the ready.

“Are you ready now, Mary? Let’s get that shirt out of the way,” and Sue and Jenny tugged at the hem and pulled it up, taking my glass and setting it aside.

I was soon self-consciously topless in front of these two lovely women and automatically folded my arms. But, unfortunately, it had disastrous effects as it only served to bunch my man-boobs up in front of them.

“Ahh, yes, Jen, I see what you mean. Some nice breasts there. May I, Mary?” Sue was beside me and pulling my arms away to inspect, and then the tape was in hand from around her neck. “Arms up please,” she added, and Jenny assisted by lifting them while Sue leaned in to feed the tape around me, her face close to my little boobs, and I felt it encircle me across my nipples and tighten at the back as she pinched the tape together to read the size.

There was a pause as she wrote on the pad, then the tape loosened and slipped under my man-boobs and tightened again, Sue’s warm hand against my chest. The pause repeated, and then Jenny smiled into my eyes as she released my arms. The glass of wine was offered again, somehow miraculously full, but I didn’t mind.

They stood each side of me as Sue explained, “Good call, Jen, Mary’s a 36B cup. But the question is, what style of bra? How firm are your breasts, Mary?”

I almost giggled at the question. It wasn’t something I had ever thought of.

“Not sure? Okay, let’s see,” and her warm hand was cupping my small boob.

“OH!” I gasped in surprise, but also a tingling feeling went through me.

“Sorry, Mary, did I surprise you? You have nice firm breasts and clearly sensitive nipples,” Sue commented as her fingers cupped me, but her thumb grazed over my nipple, which immediately stood up hard.

It wasn’t the only thing that was now hard as her full breasts brushed my arm while she seemed to enjoy continuing unnecessarily to caress my nipple – I couldn’t imagine this being a standard part of a fitting for a woman.

“I can see you will have fun with these, Jenny,” Sue said.

Jenny agreed as she joined in on my other side and copied Sue’s actions. Jenny leaned in close to my ear. “Is your little cock as hard as your nipple Mary?”

Sue heard. “Oh, really? How disappointing. Is she tiny?”

“Yes, Sue, barely my heel size when hard, which it is now, but it’s hard to tell. I know you like yours a bit bigger, sorry.”

“What a pity, but at least she has nice titties to play with. I will see what we have in a B cup. What color?”

“Pink and lacy, please. I’d like to see them stay hard,” Jenny said.

I was just a toy to play with, and Sue was gone, so Jenny leaned in to suck my nipple while tweaking the other. I was somewhere in a dream world when I heard the curtain part. Andrea’s voice startled me, but Jenny didn’t stop. “Mum said that Mary is tiny down below. Is that true?”

Jenny pulled away briefly. “Yes, tiny, just a little clitty, really.”

“Can I see?”

There was excitement in Andrea’s voice as I was stunned to hear Jenny say, “Sure, why not? We’ve teased her long enough, I think.”

“What… I … but…” I stammered.

“Shh, Mary, it’s alright,” Jenny cooed as Andrea knelt in front of me.

She tugged at my belt and zip, and my pants were falling in a few seconds. Looking down, I could see straight into her bountiful cleavage and could see her nipples standing hard against the blouse material.

“Jenny, you naughty girl! Look at these panties you made her wear after cumming in them. And now she’s leaking again. I thought you respected our products more than that!” Andrea admonished in an amused tone. “Well, let’s see what we have here then!” and she reached to the waistband and pulled them down to my ankles in one silky motion.

He flipped up out of the panties as they went down to release him and was standing as proud as he could and was a little leaky from all the arousal. The foreskin slightly peeled back from the constant female attention.

Andrea glanced up at me. “Step out, Mary.”

My pants and panties were now gone with my shoes, and I was naked in front of this gorgeous girl. Andrea reached out to fondle the ball sack as she exclaimed, “Oh dear! You’re right. Such lovely balls but a tiny little shaft. Whatever will you do with it, Jen?”

“There are lots of things, Andrea. I was always taught; it is better to give than receive, so there are plenty of things to try.”

“I guess so as long as you have fun. May I?” she asked Jenny.

I was confused, just a presence in the room.

“Yes, of course, enjoy yourself!” Jenny replied, and I felt her hand squeeze my arm as she continued to tweak my nipple.

“Ta,” was the reply, and Andrea leaned in and swallowed me into her vacuuming mouth, and she began to bob back and forth along my shaft.

Her tongue rounded the head, and she used her teeth to strip the skin back along with my cock as she pushed into me and took my breath away by catching the ridge with her teeth as she withdrew before briefly biting down and then sucking me in as she moved forward again. I’d never had a head job like it! Her hand cupping my balls squeezed as she bobbed in and out. I had to shift my feet to plant them so she didn’t push me over. Instead, she pulled on my balls harder, and they tingled in her grasp as she slurped and sucked me.

I felt her finger scratching at the trail to my backdoor, and then she found the butt plug and just stopped momentarily, perhaps in surprise. But then she was off again, and I was desperately trying not to move too much as I knew I would explode soon. She tapped the plug sending tremors inside me as she held my balls and squeezed harder – such beautiful pain, and that was it! I felt the first spasm of orgasm, and, sensing it was coming, she plunged me deep as she could and just held me there as I sprayed into her mouth. On the third shot, she pushed the plug into me and pulled away so that I leaned forward, and the next couple of strings of cum flew onto her cleavage and ran down into her tits.

“Mmmm, yum! Time?”

From behind me, I heard Sue’s voice, “One minute and twenty-eight seconds! Well done! But I think a lot of groundwork was done before you started, so it doesn’t really count,” Sue laughed.

I was stunned again and standing naked in front of three women while they talked about me, the old chill of embarrassment, turning me pink. Andrea somehow found a wipe and cleaned me up before standing.

“She tastes good, and it’s kind of nice not having to gag on something trying to push past my tonsils,” Andrea said while she casually opened her blouse to expose her awesome tits so she could wipe the cum away. “Well, back to work! See you soon.”

And again, Andrea was gone.

“Here you go, Mary, let’s try these,” Sue said as she held a stunning-looking lacy pink satin bra and panty set on a hanger for me to see. My eyes must have betrayed me as both she and Jenny laughed. “First the panties,” and she knelt before me to help me put them on as I stepped into them. “Oh, I see Jenny; now that she’s cum, she really does shrink! Well, that will be good for a neat panty line anyway.”

And she slid the panties up my legs and gently pushed my shriveled cock back in place between my legs.

“Now the bra; your turn Mary.” She offered it to me. “Arms through first and then bend forward a little to bring it up to your breasts, so they fill the cups, then fasten at the back. Try it.”

Nervously I did. Jenny just watched with a smile as I stood and blindly struggled to fasten at the back. “It’s okay,” Sue commented, “lots of girls struggle, but it is the best way to put it on, so practice.”

Soon it was in place, and Sue had adjusted the straps and checked that the cups filled and firm, and I felt a sudden sensation of just yummy.

“My, my Jen! Her nipples certainly enjoy a well-fitted bra,” Sue added with a chuckle. My nipples found every slight movement added a tingle from the lace cups, and the firm encompassing band just felt right. I’d never considered it, but perhaps this had always been meant to be.

“That is beautiful, Sue, and she loves it! Well done!” Jenny gushed. “Let’s get her dressed, and I can take her home.”

I started to move to undo the bra, only to have her brush my hand away. “That’s no way to treat a gift and all the expert help you’ve had from Sue and Andrea! So be proud and wear it; it suits you!”

Abashed and now wondering how many would notice as we walked out to the car, I pulled up my pants and slipped on my shirt.

“I believe these are yours, Mary,” Sue said as she handed me the used panties I’d worn here and smiled.

I was almost in a trance as we walked back through the shop, and again there were attentive looks from a couple of customers who were still there. Then I realized why as I passed a full-length mirror – two things: I had a pair of panties dangling from my hand, and the outline of the bra stood out clearly with a now obvious bustline against my shirt showing my boobs off quite clearly. I blanched at what they thought and then saw their smiles, and one gave a little nod of what looked like approval!

At the counter, Sue suggested, “Can I pop those in a bag for you, Mary?” as she took the panties.

I handed them over, and a small bag was returned with the shop name clearly printed on it.

“I’ll put it on your account if you like, Jen?”

Nurse Jenny said, “Thanks, Sue. We’d better get going. I’ve got somewhere to be and someone to do!” She laughed, and we headed out the door. I could see my reflection in every window as we passed in the brighter light of the mall, and my perky tits stood out. Jenny noticed me looking. “Come along, dreamer, most people don’t see anything of you while they are looking at me! Let’s go.”

And she put her hand behind me to steer me out, but her hand fell right on top of the bra band where it joined, and I felt the pressure as she massaged it to remind me.


Out to the car, and I opened her door for her. So in we got, and it was back to her place. Jenny absent-mindedly caressed my neck as I drove until her fingers slipped to my shoulder, and she fiddled with the bra strap. My mind raced, but somehow, we got back to her house. Out of the car and up the path, and she paused at the door. Jenny turned to me.

“Are you ready for anything that I say goes? Now is your chance to say no and just leave. You can keep the set I bought you.”

There was something in her eyes that demanded an answer but also her compassion in offering an escape. Her confident stance made me feel that she knew the answer anyway. I just had to know where this could lead – it was all new to me, but I loved it, even the humiliating attention.

“Yes, Jenny, I’m ready, and thank you for the gift.” I smiled.

“Aww, that’s sweet. Okay, when we go in, you strip off your outer clothes in the hallway and meet me in the bedroom.”

She turned, opened the door, and entered, making a right turn into the first room. I closed the door behind me and stood momentarily pondering on the polished wood floors of the hall that ran the length of the house with doors off each side and a backdoor visible at the end. I removed my shirt, shoes, and then pants and dropped them on a hallway chair. In the cool air of the house, my nipples stood out hard against the lace of the bra cups, and my cock stiffened against the silky panties. I took my first hesitant steps into what would be a life-changing experience. I entered the bedroom.

To be continued…


*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.


Leave a Reply

Your email address will not be published. Required fields are marked *

Translate »

You cannot copy content of this page