Jen's Journey part 4   by Brightside.

All comments welcome to: g_pi2004@yahoo.co.uk




Jen had been in Dublin now for two weeks and was starting to feel settled in. Her course was much easier than she expected and so she was able to keep up with the work without exerting herself.

This meant she spent most of her spare time masturbating.

Her experience on the plane had been a watershed for her, the first time she'd been able to act out her fantasies so fully in public. She realised she liked being used now and wasn't as dominant as she'd always thought of herself. But apart from a brief return bout with Inge (she'd taken the stewardesses number as she left the flight and had met up a few days later for an all-night girl-on-girl session that had been strangely unfulfilling) she'd had no sex since she landed.

She was getting increasingly horny.

Not able to get into student accommodation she'd taken to renting a room in a house shared with two others, a mid-twenties lawyer who was always at his girlfriend's and a stunning girl a couple of years older than Jen who was also studying the same subject. This had proved a boon for Jen as Siobhan had helped her out numerous times with how to approach her work. They would've been great friends but Jen was so taken with the raven-haired young woman that she just clammed up whenever they got to talking personal things. In fact, Siobhan had asked her to a bar this evening to meet some of her friends and Jen had declined - not that she has anything else to do, so she didn't want to stumble over her words all night like a love-struck teenager and embarrass herself.

So, still frustrated with herself for missing out on being with her housemate, and knowing the other one was definitely out, she indulged in her current favourite pastime - namely watching porn while trying to fit her fist up her arse. The thorough stretching she'd received in the cockpit should've made it easy and she didn't know why she struggled now. She'd tried it every night since she landed and the pain when she reached the knuckle stage was too intense, so she'd resorted to using her trusty old vibrator and bringing herself off that way.

The night before, however, she recalled that the co-pilot had smeared some lubricant into her that hadn't so much lubricated as numbing her slightly allowing such a huge penetration. So after college she'd shyly sneaked into the sex-shop on the way home and purchased some anal lubricant, ignoring the smirking guy behind the counter.

She lay out on her bed, turned on her right side towards the door of her room and looking at her laptop playing some hardcore lesbian porn. She smeared her left hand with lubricant and worked some into her ring, clenching slightly at the cold. On the screen a beautiful blonde with pert tits was thrusting into a larger red-haired lady with a strap on nearly as big as Jen's arm. It was so hot and Jen quickly had her fingers together in a beak shape and was pushing them into her up to the first knuckle on her index finger.

The lubricant was definitely doing something, not so much making it glide any easier, but making her feel colder, number. It felt a bit weird but she soon got used to it. She pushed harder and had all five fingers in her up to the second knuckle, feeling deliciously stretched already. Her thoughts drifted from the porn to Siobhan and she withdraw her hand slightly before thrusting it further into herself, almost to the widest point in one go. She gasped in pain, but it was a good pain and with her right hand she stroked her clit, sending pulses of pleasure through her.

Again she withdrew slightly and pushed harder, quickly reaching the widest point - her arse splayed obscenely wide open - and then she took a deep breath and gave it one big effort. As the widest point went past her anal ring it suddenly snapped down onto her wrist and with a grunt of satisfaction Jen came, squirting slightly much to her surprise.

`Uuuuuuurrrrnnnnnngggghhhhh!!!!!' was all the noise she could make as she felt this huge shape in her beautiful arse. She frantically strummed her clit as she built to another orgasm - and then heard the knock at the door.

"Jen, are you okay?" said Siobhan. Panicking, Jen killed the video on her laptop and tried to pull her fist out of her arse at the same time, but she'd tensed up at hearing Siobhan's voice and her fist wouldn't come out.

"I..I...I'm o-okay!" blurted out Jen as she pulled harder, feeling way more pain on the way out than her fist had on the way in.

"Are you sure? I heard you cry out?" Siobhan asked through the door, concern in her voice.

"No, no, I'm fiARGHHHHH!!!" yelped Jen as her hand popped audibly from her arse with the most intense pain Jen had felt in years - tears springing to her eyes instantly. Her door started to swing open and Jen quickly covered most of her body with the duvet, only her large breasts mainly visible. Siobhan's head appeared around the edge of the door, "...well that sounded like you were far from fine. What's up?" she said enquiringly. Her eyes briefly taking in the scene and her cute upturned nose wrinkling at the smell of Jen's sex.

"Oh, god, I'm sorry!" she blushed starting to back out until she saw how much pain was Jen was in, at which point she fully entered the room and approached Jen's bed, sitting on the edge as Jen, mortified at her crush being so close to her at such a moment, said nothing but tried to cover her breasts by pulling the duvet up more with her left hand.

"It's okay Jen, we all do it," she said kindly, "I'm always a bit frisky when I start my period too." Siobhan giggled. "But why the tears? What's wrong?"

Even through the pain, Jen was puzzled. "I'm not on my period."

"Well, where's all the blood from?" asked Siobhan, equally puzzled. Jen looked down horrified as she realised her left hand had a lot of blood on it and it was all over the duvet where she'd held it.

"Oh god," she moaned as she realised the wetness around her arse wasn't lubricant like she'd thought initially. The pain was not as bad as it had first been but it really hurt. "Are you hurt?" asked Siobhan, "Show me," she demanded, pulling the duvet away.

Jen tried to cover herself, but noticed Siobhan's eyes alight on her nipple bars with interest before she asked, "Where are you hurt?"

Jen couldn't see a way out of this. "Um, my bum. I was, um, playing," she said lamely, blushing and not able to look Siobhan in the eye. Siobhan rolled her over and parted her cheeks - Jen felt powerless to resist. "My god, what were you.....doing....." she glanced at Jen's hand and saw the blood up to the wrist, "....ah, and you managed it I see. Was it good?"

Jen was taken aback at the question and looked back over her shoulder. "It was until the end," she said, then laughed when she realised what she'd said. Siobhan laughed lightly too and slapped Jen gently on the behind, turning Jen on despite the pain in her arsehole. She shivered. "Oh I'm sorry," said Siobhan, mistaking the movement for pain, "there you go." With that, she leant down and kissed Jen's left buttock where she'd slapped it. Jen nearly came.

"Well you've torn your ring I'm afraid," Siobhan said, all businesslike suddenly, "you'll have to go to the hospital tomorrow after I clean it up tonight. Shouldn't need stitches though, it's only a small tear."

"Hospital?" Jen said in astonishment, "but people will find out! My god, my parents!" Jen rolled over and struggled to sit up, but Siobhan held her in place. "Hush, and hold still before you do yourself any further damage. Hmmmm, well you could go and see a doctor I know at the hospital rather than going to A&E. He's very discreet - always helped me with my problems," she said with a smile.

"Problems?," Jen asked weakly. "Yes, but enough of them. Wait here while I get something to clean this up," said Siobhan, standing up and giving Jen's rump a little slap. Jen stayed where she was as she heard the other girl moving around in the bathroom before returning with a steaming bowl and a bottle of antiseptic.

"Okay," she said truthfully, "this is going to hurt you a lot more than it'll hurt me."

Jen tried not to cry as Siobhan cleaned the wound and applied antiseptic but it was all too much and before it was all done she'd passed out through exhaustion.



The next morning Jen awoke face down on the bed and very sore. She rolled over on her side and saw the Siobhan had dressed the wound and placed her knickers back on, and on her pillow was both the name and address of a doctor and a sealed envelope addressed to the same person.

Gingerly she got dressed and with no lectures or workshops that morning she decided to head straight to the hospital to get her bumhole seen to. She felt embarrassed enough about Siobhan knowing but her kindness the night before had eased it somewhat. She hoped this doctor (a Dr. Anderson) was as discreet the other girl had said.

After taking the bus (walking was painful) she arrived at the hospital and proceeded to the 5th floor as directed on the note Siobhan had left for her. She easily found the waiting room and reported to the receptionist, noticing that she was the only other person there.

"Yes?," said the receptionist frostily.

"Um, I've been told to come and see a Doctor Anderson?," mumbled Jen, thrown by the older woman's hostility.

"Well the doctor isn't seeing patients today, so please leave," the receptionist said with a nod towards the waiting room door.

"But I have a letter for him!," Jen said in a pleading voice that grated even to her as she handed over the envelope. "Please give it to him!"

The woman stared at the envelope like it was a puppy that had just crapped on her new living room carpet, before reluctantly rising and taking it without a word, leaving by a side door. Jen gently sat down on a padded chair and sighed in relief.

It lasted all of 2 minutes before the older woman returned and beckoned Jen to follow, leading her through the side door and into the doctor's office where a mid-forties man was bent forward over a desk filling in paperwork.

"That will be all Gladys," he said, "you may as well take lunch now."

"Yes Doctor," she affirmed, before closing the door to the office behind her.

Jen patiently stood in front of the desk as the man finished his form and then glanced up smiling. He was ruggedly attractive thought Jen, temples just greying but with an impish grin that put her at ease. "Please Jen - I may call you Jen? - have a seat," he said, gesturing towards a chair to Jen's right. "Siobhan has told me your problem so we may as well get right down to helping you out." Jen blushed slightly and cast her eyes downward.

"Oh no need to feel awkward," he laughed lightly, "you won't be the first and you won't be the last. Now if you could just pop behind the screen behind you and remove your clothes, I'll be with you in a minute."

Jen moved behind the curtain across half of the room and removed her clothes and neatly folded them onto the treatment table. She thought about whether we should remove her top or not, but decided to keep her bra on as he wasn't going to be examining her top half. Naked now except for a wispy lace bra that barely hid her prominent nipples, she leant back against the treatment table - the fleshy part of her arse protecting her delicate and hurt hole.

She waited a few minutes until she heard a chair scrape in the room and the doctor approach and pull back the side of the curtain.

"Ah, all ready then?," he said, a cool detachment in his eyes that seemed very professional. "Okay, if you'd like to bend forward over the table for me?"

Jen turned round and bent forward, bracing herself on her elbows as the doctor pulled up a chair and sat down behind her.

She heard him snap a latex glove on and felt her cheeks being pulled apart. She blushed even more at the thought of a stranger looking right up her intimate places like that.

"Hmmmm, okay, well I see what you've done here - arch your back slightly please - yes....well it's not a big tear and Siobhan did a decent job....okay." Jen felt something cold applied to the torn area and felt the pain lessen considerably. "I don't think you'll need stitches," Jen sighed in relief, "we'll just glue.... this...bit," Jen felt something hard pressed against her which didn't hurt at all, then the pressure eased.

"Okay," said the doctor, standing up and removing the glove, "all done. You'll feel some pain for a couple of days during bowel movements but should be fine after that. Obviously I'd not recommend trying that again for a while, " he turned to look at her with a smile as she pulled on her lace knickers. "Return here at this time in a fortnight and we'll check on your progress."

With that he returned to the other side of the curtain while Jen finished dressing and was back writing notes on his desk when she emerged herself. He seemed disinterested so she simply said "Thanks" and let herself out. The receptionist wasn't at her desk in the waiting room when Jen reached there so she shut the door behind her on the way out and made her way home.

The next week passed uneventfully. Siobhan never mentioned what had happened but Jen caught her glancing at her smiling out of the corner of her eye a few times but she was still too embarrassed to say anything to the older woman. The doctor had been right about how painful her bowel movements were but after 3 days it didn't hurt so much and by the end of the week she felt no pain at all. Her only problem was a complete lack of sex drive on her part. She normally masturbated several times a day but whenever she felt like it a dull pain in her bumhole made her lose interest quickly. So by the time she was due to visit the doctor again she'd managed to come once in two weeks and was intermittently horny as she could be and equally passionless in turn. It was driving her crazy!

When the fortnight was up she returned to Doctor Anderson's office in a grip of excitement. Her short journey on the bus had turned her on immensely, and even such a older man as the doctor was seeming attractive to her now. The receptionist coolly directed her to a chair in he waiting room while she spoke to the doctor on her phone. It was all Jen could do to stop squirming on her seat. The thought that he'd be able to see her state of arousal both appalled and excited her more.

Once more the receptionist led the way to his office and closed the door behind Jen. The doctor was looking at something intently on his computer screen and glanced up as she arrived. He grinned broadly. "Ah, Jen, nice of you to be so prompt! I'm just checking your notes now." He looked at the screen again before turning his gaze to her.

"Right, well we'd better have a look at how that's healed. Before we start the examination however, I have a small favour to ask." Jen was puzzled. "Um, what do you mean?"

"Well obviously your visit here has been kept confidential as Siobhan requested and all payment has been waived." Payment!, thought Jen, I didn't think about that! She started to worry now, all arousal forgotten. The doctor noticed the look on her face. "No, don't worry about that, as I said it's all taken care of. We fund the use of experimental treatments such as those used on yourself by sharing our work with the hospital in general. I was going to ask if you minded the medical students in my group attending the examination?"

Jen was taken aback, but didn't see how she could refuse the request. After all, one doctor looking at her wasn't much different from two or three. "Um, yes okay," she said quietly. The doctor beamed. "Splendid!" He reached for the phone and pressed a button on the handset. "Yes, it's me. Please send in Andy, Charlie and Katherine."

Or four, thought Jen wryly.

The door opened and a young woman entered, about Siobhan's age, followed by a man and a woman of the same age. All three wore white coats and held a pad and pen in their hands. The doctor stood from around the desk and approached Jen. "Katherine, Andy and Charlie," he said by way of introduction, indicating them in the order in which they'd entered the room. Katherine was Jen's height about 5' 9" and had shoulder length brown hair tied back in a ponytail. She had a slender frame but very prominent breasts. Andy looked to be over six foot and clearly worked out a lot. His blue eyes looked at her intently beneath his floppy blonde hair. Charlie was a petite thing, probably only 5' 4" with a boyish figure and long blonde hair.

Jen was mortified. They were all stunningly attractive. She started to feel herself heating up as they looked at her in that studied way doctors use to let you know who's boss.

"Right, well Jen, if you'd like to remove all your clothes for me and step into the robe provided? I'll be in shortly." He motioned her towards the curtain with a hand on her elbow. Jen started, and quickly moved behind the curtain and started to undress. There was indeed a green robe hanging up for her that tied at the front of her neck but was split up to the small of her back. At least she would be covered she thought as she removed all her clothes and the slipped the robe on, tying the strings beneath her chin. She heard the doctor explaining to the others on the other side of the curtain.

".....so as you can see a small tear in the anal ring caused by an excess attempt at self fisting by the patient....."

Jen's jaw dropped.

"......but this new binding glue combined with enzymes to promote muscle repair should have returned the anal ring to all it's glory. Now, we shall examine the patient."

He pulled back the curtain allowing the three junior doctors to enter first while Jen sat on the examination table unable to meet any of them in the eye. The doctor approached her, "If you could resume the same position as last time you were here please?"

Jen stood up and turned round, again bracing herself on her elbows as she felt the robe naturally slip either side of her buttocks exposing herself to all their gazes. Jen burned with embarrassment.

She heard a latex glove snap into place and her cheeks part as the doctor began talking to the three others behind him. Jen felt something cooling and wet smeared around her anus. She felt very, very horny all of a sudden and almost automatically reached for her itching clit, only stopping her self in time.

"...as you can see the tear appears to have healed quite nicely and a gentle amount of pressure....", she felt a lubricated fingertip push into her arse which only made her hotter, "...and the ring is holding integrity nicely. Now to test the healing properly we'll have to apply more pressure on the afflicted area." Jen felt the fingertip withdraw only to be replaced by two fat fingers which slid into her with ease. She couldn't help but moan in lust. "As you can see," the doctor continued, slowly sawing his fingers in and out of her clenching arsehole, "as anticipated the patient is incredibly responsive to stimulation in the anal region, as can be seen by the wetness around her vaginal region." Jen realised she must be leaking copious amounts of pussy juices but at the time she didn't care, the fingers felt too good. She'd been missing this for too long.

The fingers withdrew. Jen gasped in disappointment, but melted at the next words she heard.

"Charlie, why don't you now examine the patient and the strength of her anal ring?" She heard another glove pulled into place and felt a much smaller finger than before pushing into her. "Very good," said the doctor, "now try a second finger, yes that's good, now a third - look how the patient arches her back in appreciation - now push your thumb and little finger together like so.... yes....now push slowly and watch the newly repaired area closely."

Jen was in heaven. The tiny hand, much smaller than her own, pushed slowly into her arsehole, stretching her to just over half of the width of her own fist. She fought to deny the orgasm that was building, not wanting to come in front of these strangers, but as the widest part of Charlie's fist slipped inside and her arsehole clamped down on her wrist she came with a small scream and shook violently. Charlie flexed her fingers inside Jen's rectum with a fluttering motion that made her come again straight away.

"It's so hot in there," Jen heard a woman's voice say in amazement as Jen's struggles subsided and her breathing slowed to deep gasps. "Okay," said the doctor, "clearly the healing has worked to such a point. Now Charlie if you'd like to slowly remove your hand....." Jen grunted in a mixture of pleasure and pain as the small woman pulled out far too quickly, luckily she didn't feel the same pain as before so didn't think she'd torn that time. "Now Katherine, if you'd be so kind as to continue the examination?"

`What!?!', thought Jen, `what does he mean continue? Someone I don't know has just fisted me in the arse!'

She struggled to stand up and felt a firm hand on her back holding her down. "What? What are you doing?"

"Quiet Jen," said the doctor soothingly, "we must complete the examination to determine if you've healed properly. We can't leave you with a weakened sphincter. The only way to test properly is to stretch you to the same level and show that no more tearing occurs. No please be quiet."

Jen wanted to protest and opened her mouth to do so, then just grunted as she felt a much larger hand pushing into her. `Okay,' she told herself, `I'll let this happen but then I'm leaving.'

And then, frankly, she didn't care anymore as her ring stretched delightfully past Katherine's first knuckle. "Unnh, yes!" she gasped as the hand went further and further, stretching her to a point nearly as wide as she'd ever been with herself. The pain built up as the junior doctor pushed harder, becoming almost unbearable, and then with a huge scream Jen had the biggest orgasm of her life as the hand pushed in to the wrist.

"AAAAIIIIIEEEEEEmphf!", Jen howled and then was cut off in her prime as a large hand clamped over her mouth. Her eyes rolled back in her head and her buttocks wobbled as she trembled from fingertip to toes in ecstasy.

"Now, " exclaimed the doctor, "pull it out!" Katherine did so roughly and Jen peaked again, and then again as it pushed fully back in again. The junior doctor started pulling her hand out and then roughly forcing it back in, twisting it around as she did so. Jen never stopped coming all the way through as her arsehole was thoroughly stretched over and over again, the pain making it all the more enjoyable.

"Now form a fist inside her, " instructed the doctor and Jen felt something indescribably good as Katherine formed a huge balled fist inside her bowels. "Now slowly pull it out, slowly.....that's it....look how wide she can stretch....slowly.....that's it!" Jen's eyes bulged in agony as the fully formed fist pulled out of her, the pain soon transforming into yet more pleasure. She's stopped coming for now and was just enjoying the thorough fisting she was getting.

Katherine pushed forward with her clenched fist, stretching Jen much faster this time, but the previous action had loosened her nicely enough that it just felt amazingly good, before pulling out again. Once more she started punching in and out of Jen's abused arsehole sending bursts of pleasure each time she was fully stretched.

Then suddenly she stopped. Jen rotated her arse in expectation of more, hell, she wanted more now.

"See how the patient remains dilated even after the fist is removed? Well done Katherine, excellent work. Now Andy?"

Jen didn't even hear a glove this time before feeling a much larger hand pushing into her in the beaklike shape. Oh wow, this was much bigger than the previous girl's hand and therefore much bigger than anything she'd taken before and she couldn't help but notice that the hand was indeed ungloved - clearly this was no longer a medical examination.

She no longer cared and moaned into the doctor's hand still tightly held over her mouth. Andy's hand was now stretching her further than even Katherine's fist and was still going. The pain became intense and she tried to pull away to get a breather, but was unable to due to the hand on her back. She struggled to stop the huge invader going in further but to no avail, tears started streaming from her eyes as the pain felt almost as bad as when she'd torn herself.

"Help me hold her," said the doctor and she felt the female doctors' hands on her shoulders and legs, prevented her from moving much. Still the hand pushed on and Jen was sure she was going to split again. She screamed into the hand covering her mouth and tried flailing her limbs, but she was held too tightly.

And then it happened. She reached the widest point and the hand drove into her about 6 inches, way past the wrist. Jen came, emptied her bladder all over the man standing behind her and then passed out.....


....she came to sometime later, not too long to judge by the fact that the huge fist was pistoning in and out of her gaping arsehole. She heard voices talking distantly as her hearing slowly returned.

"....well when you showed me the video I didn't think she could take it...."

"....what an anal whore, she nearly sucked my arm off..."

".....I could park my car in that now, look at how wide she's gaping with Andy...."

Jen realised she was no longer held or indeed gagged and as the huge clenched fist popped free of her again she moaned in a mixture of pain and extreme pleasure.

"Ah, she's awake," she heard the doctor say. "Andy, you can stop your fun now. It's time to move onto the next stage of the examination....."


Continued in part 5....




