Careful What you Sign up for

Part Three

“Come on ladies, I need to pick up some stuff before the party, it’ll only take a second and I know y’all want to look around too” Misty exclaimed taking Matty’s hand and pulling him towards the store. It was the one place on campus Matty had never been for a number of reasons. For starters he wasn’t interested in most of the products that they sold in this particular store because the internet gave him unlimited access to anything he might need from the store but much more privately. Secondly he was far too embarrassed to be seen coming or going from the store that was parked at the end of Greek row despite how busy it was on a regular basis and the fact he probably wouldn’t be recognized. Lastly, being an adult novelty store on campus, it was a rarity. For years the school had tried to have the store shut down, moved, or straight up bought out but the student body and particularly the Greek row had fought vehemently to keep the sex store open despite the taboo image it had on the campus image. 

Matty felt his feet moving to keep up with her hand pulling him towards the door. Part of him wanted to stop and turn back but his body refused and he followed her step by step to the door, finding himself smile with delight. He was embarrassed enough to be out in public as is, the only redeeming quality was no one would recognize him. Ashley stepped up behind him and pushed her ample chest into his back when he froze inside the door looking into the store at the large selection and variety of adult toys. He felt himself gulp and start to burn up when Ashley whispered into his ear “what’s wrong sugartits, never been in a sex store?” She reached up under his arms and grabbed the prosthetic breasts and gave them a good squeeze from behind. Out of nowhere, he became almost insatiably horny and Ashley gave him a little push into the store. He stumbled a few steps forward which gave room for the other girls to enter behind him. 

The girls separated to do their own shopping while Matty clung to Ashley’s side. She grinned evilly as she strolled through the most provocative section of the store which openly displayed almost every type of dildo and butt plug. Everything from realistic to vibrating and large non humanoid plastic prosthetics lined the shelves. Ashley stopped and took hold of a rather large realistic dildo and stared into Mathew’s eyes as she began to stroke the length. Mathew couldn’t explain why but all of a sudden he too wanted to stroke the dildo, admiring the size with a whisper in the back of his head questioning what it’d feel like inside of him. He pushed the thought from his head when Ashley took his hand in her free hand and put it on the dildo above hers. Almost instinctively he began to stroke it, getting more horny with each pass. She removed her hand and watched for a moment till Matty realized he had the attention of all of the girls when he snapped out of it and quickly pulled his hand away. Ashley continued to grin maniacally as she took his hand and pulled him over to the scant lingerie. 

She sorted through the stringy garments briefly and pulled a few off the racks and tossed them in a basket that Matty had not realized she grabbed then quickly pulled Matty towards the dressing room before he could look in the basket. She shut the door behind her and locked it and almost in a blink had slipped out of her dress. She pointed towards a chair in the corner commanding Mathew to sit with her glance. She was standing in her undergarments when there was a light knock on the wall. She grinned and stepped towards the wall where Matty saw what looked like a small door built into the wall. She opened a small latch and the door swung open. Matty saw a hand come through with a $20 bill which Ashley snagged before stepping away from the wall. Seconds later a dick was fed through the hole. It was already raging hard, probably about 8 inches long but skinny. Matty was stunned, he had never seen a glory hole in real life nor had ever expected Ashley to be a participant. 

“Go on, it’s not going to suck itself” she said as Matty sat frozen in the chair. He turned to look at her shocked. “I’m not going to let you watch me undress so keep yourself occupied over there and I have no intention of sucking that dick and he already paid.” She said sounding a little domineering. “Then why did you take his money or open the door in the first place” Matty tried to argue. “Because $20 will help pay for my new lingerie, now suck his dick and be a good girl. You’ll need the practice going out dressed as you are and you wouldn’t want a jock to discover you don’t have much more to offer other than being the punch line of a bad tranny joke at the end of the night” she justified sounding ticked off a little also hinting at some pretty damning blackmail. Despite his best efforts to refuse, his body started to act though, he could feel himself being pulled towards the hole almost excited to suck the length poking through the wall. “Wrap him up first, no telling what you’re going to get with a glory hole” Ashley said breaking his trance when he realized he was already on his knees in front of the hole, his hot breath tickling the head of the shaft inches away from his face. Ashley had covered her chest as he turned around to look at her where she nodded towards a small shelf with a couple bottles of lube and a bin of condoms. 

Matty reached up and pulled a condom out, tearing the package open with his teeth while his free hand latched on to the length and began stroking. He placed the condom on the head then slowly rolled it down, using the lubricant of the condom to aid his stroking. ‘Why do I feel like I’m so good at this and how am I doing this’ was the only thought to pass through his head before taking the head into his mouth. The cherry flavored numbing lube helped a little as he began to bob up and down on the length. Breathing through his nose he found himself progressing further and further. His body seemed to be on autopilot till he realized his nose was touching the wall, the entire length stuffed down his throat, and Ashley was snickering behind him with her phone recording  while he deep throated the strangers cock for several seconds. Matty pulled off and turned to tell her to stop before he realized she was completely naked. “Keep going, if you slow down or stop now it’ll only become harder to finish him” she said as she took a few step towards him while he was on his knees. 

Matty continued as Ashley knelt behind him and pulled the basket towards them. Matty felt the skirt of his dress pulled up from behind. The angle he was crouching and the tightness of the fabric made it perche perfectly on top of his ass cheeks. He adjusted instinctively when he felt her fingers hook into the waist band of his underwear and pull down till they rested on the floor trapped by his kneeling position. He saw out of the corner of his eye her hand move up to the small shelf to grab a bottle of lube, curious as to what she was doing but still focused on the task at hand. The condom had greatly reduced the effect of his tongue but he just knew in the back of his head that he was going to get this guy off one way or another. 

Moments later he felt Ashley rubbing and groping his ass which added to his fire and despite being horny as all hell, he wasn’t getting an erection. “You have a very nice ass” Ashely whispered in his ear before his head bobbed back forward. Her fingers traveled down in his ass crack which had been naired smooth where her finger teased his rosebud. She paused for a second and took her hand away before with a sudden return her lubed pointer and middle finger forces their way in. Mathew expected it to hurt but instead her fingers pressed firmly on his prostate which almost made him double over in ecstasy. For a few more second she probed his inside before her hand pulled away again. 

Now something new and hard was pressed against his ass. With some extra lube Ashley toyed with the butt plug, pressing the tip of the tapered plug in and out a few times before pushing it in deeper. The first bulb of the plug was only about an inch and a half in diameter which lead into two more bulbs each increasing in size before tapering back down again. Ashley seemed to become impatient and pushed harder to get the second bulb in thinking ‘you’d think he’d be a little looser after the machine had a go at him’ to herself. 

With the second bulb in she paused for a second and reached between his legs, finding a hold on his still flaccid dick. She gently tugged, rolling his head between her fingers. Her hand was so expertly skilled and felt beyond glorious, if he hadn’t been sucking the dick in front of him it would have been every fantasy of his to get a hand job from his childhood crush. He let out a few moans into the cock that was bulging in his throat but made sure not to let his teeth ride on the length

Ashley let go of his dick now and returned to the plug which was at the last bulb. She quickly rammed the plug home in one final aggressive push.  As Matty blacked out for a second he tilted all the way forward against the wall. Ashley forced her fingers through his long brunette hair and held his head there. He began to choke briefly as his air flow was cut off. “You can cum now” Ashley commanded in his ear and right on cue he almost doubled over again in ecstasy, his flaccid cock giving up the pent up load onto the floor. At the same time he finally felt the pulsation of the cock in his throat, finally giving up the seed he’d fought so long, the spasming of his throat muscles choking on the cock sending the guy over the edge. Ashley continued to hold his head against the wall despite his struggles to push away. “Nuh uh, not till he pulls out, even though he’s wearing a condom you earned that load and it’d be wasteful to not let any of it spill down your throat, you sexy little slut” Ashley seductively whispered into Matty’s ear. The guy pulled out after a few second and Matty gathered himself trying to catch his breath. It took him a few minutes to recover from his own orgasm and catch his breath. He had never cum before without being hard and didn’t know exactly how he managed to stay soft despite being overwhelmingly horny and reaching his climax.

Realizing that there was now several inches of hard plastic in his rear. He reached back to feel the base of the plug but Ashley swatted his hand away and pulled up his panties and fixed his dress. She slammed the door in the guys face as he looked down trying to get a view in to see who he had just paid for.

“What did you put inside of me” Matty finally asked as Ashley began to dress herself quickly to leave. “Just giving you the full experience of one of the girls is all, Misty is a little wild so she probably has a vibe shoved up her cunt keeping the oven warm for the boys tonight and you’ve probably never been on the receiving end of penetration so I figured you’d really need everything you could get while I’ve still got you dolled up and being so adorably subservient.” Ashley justified. Mathew had so many questions as to why he was going along with this. Mentally he was appalled to have gone as far as wearing panties but everything on top of that was just more than he’d ever consider. Internally he was trying to fight back but everything she said he did without question yet he couldn’t voice any of his own questions racing through his head. “You’ll be fine, it’s all just fun, you look every bit the part and I doubt anyone besides us girls will become the wiser as long as you can keep up the act.” Ashley said as she took his hand and unlocked the door. 

The other girls were already standing at the register checking out with a few items each. A couple of boxes of condoms, some lube, Misty with an empty remote controlled vibrator box, stuff you’d really only find at a sex store. Finally Ashley stepped up with just a see through red thong and the now empty butt plug box. “I take it you’re already on the test run” the clerk said scanning the box. “Yes she is” Ashley said holding up a small remote and clicking a button. The plug came to life, vibrating against his prostate which made him let out a little yelp and stand up straight turning red. His own feminine voice startling him thanks to the voice changer. “I see that’ll be...” the clerks voice trailed off to Matty as the pulsation was getting him real close to the edge again. Ashley took his hand and pulled him outside and shut the vibrator off with “can’t have you soiling those panties yet there big girl, you still have a full night ahead of you and I still have the remote.”