TransgenderChapter 4 of 7Ongoing

Erin Pays the Rent

Erin Pays the Rent Pt. 04

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Erin Pays the Rent Pt. 04

As the bus trundled across town towards the college, Erin continued to think back to the past. As a high school senior, Aaron was facing big questions about what he would be doing next. Should he be applying to colleges and universities? Or just get a job to make some money while he sorted this out? Unfortunately, although his mom loved and cared about him, she was too frazzled from her heavy work schedule to be there for him as he struggled with these major life choices. And he did not really have any friends at school he felt close to.

One big change was the regular presence of Jeff in his life. Jeff would often ask him questions about what was going on. He knew Aaron was in his last year of high school, and a little about his interests, so he tried to get more information out of him. Did he drive? (No.) Any girlfriends? (Hah!) Favorite sports teams? (Not really on his radar.)

Eventually, Jeff casually asked Aaron when his birthday was. Aaron wasn't sure why he wanted to know, but he admitted that it was coming up in a little over a month.

"So, if you're a senior, you'll be turning eighteen?" Jeff asked.

"Yup," Aaron replied. Only later did it occur to Erin that this detail was important to Jeff for a very specific reason.

After the first time watching porn, Jeff had been careful not to make it a regular thing. Usually they would just talk, or stream something on his TV downstairs. Maybe one time out of four or five, he might tentatively ask if Aaron wanted to look at some porn again. Basically, Aaron wanted to look at porn all the time, but he did not feel he could ask Jeff--it had to be Jeff's idea. But whenever Jeff suggested it, Aaron would try to be at least slightly nonchalant when replying that yes, he might be interested in watching a little porn.

It always played out the same way, with Aaron having to excuse himself as soon as the video they watched was over, rushing home to masturbate. Although Jeff acted as if he was following a fairly random pattern with his choices, Aaron noticed that the subject matter seemed to evolve in a discernable fashion. Specifically, although things started out with fairly "vanilla" videos of one guy and one girl, he began to add new content to the mix: interracial, 2 guys on 1 girl, anal, and even a little light BDSM. Each new type of depravity elevated Aaron's excitement level further, and increased his now near-constant desire to be looking at porn. But Jeff kept him on a strict diet.

When he jerked off, Aaron would try to remember the most titillating aspects of the videos he had viewed most recently. In his mind's eye, he would imagine some variation on a cock going into some orifice--mouth, vagina, anus, maybe more than one of the above. He also noticed that his imagination would focus on the penis in question, and he would try to remember anatomical details, such as size, shape, skin color, etc. On those occasions when the ejaculation was shown clearly, he would lovingly imagine the blobs of semen shooting out the end of the hard-on, and splattering against the flesh of whoever was on the receiving end. That was usually what he was thinking about when he climaxed.

Aaron's eighteenth birthday came and went. His mom made him a nice dinner, and gave him a hundred dollars to spend on whatever he wanted. He appreciated it and gave her a big hug, but he wished he had some friends he could share his good fortune with. On the other hand, he remembered that Jeff had asked him about his birthday, and he wondered idly whether he might end up giving him a present. Well, he couldn't count on that, but he would see what the future brought.

In due course, he found himself heading to Jeff's after having received a text while at school. He was unusually excited about going over--it had been a while since they had watched porn, and of course there was that possibility of a gift. Jeff's door was open when Aaron arrived, so he walked in. He called Jeff's name, and from downstairs Jeff told him to close the door and come on down.

Aaron did as he was told, and found Jeff in his media room scrolling through a menu of porn. He immediately felt a jolt of excitement run through him--would he see something new and different? He took a seat on the sofa and watched the menu. Eventually, Jeff selected something called "Two On One Fun" and cued it up. Then he plopped down in his usual chair on the other side of the room.

The video started with a young-looking girl--probably barely over 18--with her brown hair held back in a ponytail sandwiched between two large guys. Everyone was dressed, the girl in skirt and tank top, the guys in jeans and t-shirts. She was kissing first one and then the other guy while they both ran their hands over her body, which was thin and lithe with small breasts. It seemed as if she was not wearing a bra.

Aaron was enjoying this, imagining he was there. He pictured himself as one of the guys, and felt a surge of excitement at the thought of fondling a cute girl like this. Then his mind took a left turn and he imagined being the girl and getting manhandled by two large guys. This provoked a much stronger burst of arousal, and he could feel his dick starting to harden.

Now the girl pulled off her top, and indeed she was naked underneath. Her pink nipples were erect, pointing out from her small, pert breasts. Then she slid off her dress, but kept on her panties. The guys pulled off their shirts, revealing muscled torsos nothing like Aaron's skinny body. The girl knelt on the floor between them and began fiddling with their belts and the fasteners of their pants, quickly pulling everything down to display their genitals. Neither was fully erect, but both seemed to be well endowed. After they had stepped out of their pants, she took a cock in each hand and began stroking it while licking her lips lasciviously.

This went on for a few minutes, and the penises steadily grew and hardened. In the end they topped out at perhaps six and a half inches for one guy and seven for the other. As usual for porn, they were circumcised. Aaron was growing uncomfortable watching this. He wanted to see the whole thing, all the way to the money shots. However, this was turning him on so much that he worried he might have to excuse himself and run home.

He glanced over at Jeff to see what he was up to, and caught Jeff staring right at him. It gave him a peculiar feeling. Jeff raised his eyebrows and then briefly glanced down at Aaron's crotch, making him even more uncomfortable.

"You know, you don't have to run home man," Jeff said. Then he reached over to a table on the far side of the chair and handed Aaron a box of tissues.

His meaning seemed clear. He was inviting Aaron to go ahead and masturbate in the room while watching the porno. Aaron didn't know what to do--he badly needed to pleasure himself, but he was kind of horrified at thought of doing it in front of someone else. Before he could go into a complete tailspin of doubt, Jeff solved the problem. He pushed down the sweatpants he was wearing and released his fully erect dick. Aaron flinched at the sight of another guy's cock so close to him, but then watched in fascination as Jeff began gently stroking its shaft. This was really hot, and the resulting arousal made Aaron's trapped boner even more painful.

It didn't take long for him to make his decision. He undid his jeans and pushed them down to his ankles along with his boxers. His no longer constrained dick immediately sprang to attention, all four and a half inches of it. Glancing again at Jeff's hand on his cock, he estimated that Jeff's dick was at least a couple inches longer and much thicker. It embarrassed him a bit, but not enough for him to pull his pants back up. Instead he started stroking his own straining hard-on.

Now he looked back at the screen. Things had escalated--the girl was sucking on one guys cock while stroking the other with her hand. Periodically she would change and suck the other dick while jerking off the one that had been in her mouth. Aaron loved this--it was exciting to imagine it happening in real life, and he found himself admiring the girl for her diligent servicing of two cocks at once.

Eventually, the guys stopped her and then one of them knelt in front of her, indicating that she should get on her hands and knees to suck him. She enthusiastically did so, and once she got started the other guy pulled down her panties and started fingering her pussy. It was pretty obvious that she was very wet, and he quickly slid his cock in and started fucking her. She was making a lot of excited moans as she got penetrated, and then she slipped into a rhythm, rocking her body forward and back so that as one dick slid out the other one slid in. It almost looked as if a single long pole ran from her vagina to her mouth. Aaron later learned that this was a position called "spit-roasting."

The girl was yelping with excitement as the two cocks penetrated her. It was a huge turn-on and Aaron felt his own sexual excitement rising. Suddenly, he caught a movement out of the corner of is eye and turned to look. Jeff was standing up and walking over to the couch, his erection bobbing in the air as he walked. What was he up to?

Jeff plopped himself next to Aaron on his left. With Jeff sitting right next to him, Aaron suddenly lost his nerve and stopped sliding his hand up and down his hard-on. He had no idea what was going on, but he was pretty worried that things were somehow going off the rails. He wondered if he needed to pull up his pants and make a run for it.

"I can do that for you," said Jeff, staring at Aaron's dick. Aaron experienced a wave of shock, embarrassment, and fear when Jeff's words sank in. He wanted to jerk him off. What should he do? He didn't want to offend Jeff, but he had not been expecting anything so...hands on. He sat there, not saying anything.

Finally, Jeff apparently interpreted silence as consent, and reached over and put his right hand around Aaron's dick. It felt strange and scary to feel and hand on his erection that was not his own. Aaron shivered from a mixture of excitement and discomfort. He didn't really want to be in this situation, but he was also feeling kind of turned on. Jeff started gently moving his fist up and down, and good feelings began emanating from Aaron's groin.

It was weird to watch Jeff's hand on his dick, so Aaron returned his attention to the video. It was just in time for him to see the guy taking the girl doggy style pull out, then penetrate her again--but the angle was different. He was trying to fuck her in the ass! The girl cried out in surprise and outrage around the big dick in her mouth, then this was followed by a yelp of pain as his dick went deeper. She tried to pull herself off of him but he had his hands on her waist and was holding her firmly. Meanwhile, the other guy was pumping his erection in and out of her mouth. She was stuck.

As the guy in back went deeper into her ass, the girl's face got red, and Aaron though he saw tears leaking out of her eyes as she squeezed them shut and whimpered. She seemed to actually be in pain. However, the two guys were not interested in that. They began pounding her from both ends, with her staying still between them, just trying to ride out the storm. Aaron found this both terrible and extremely hot, and his excitement grew. Jeff continued his stroking.

Suddenly, the guy in pulled out of her mouth and held his cock as it twitched and unloaded seven or eight big shots of cum on her face. Her eyes were still closed, but she flinched as the cum splattered on her eyelids and cheeks. He was groaning loudly as he shot his load, and the guy in back was cheering him on. Soon enough the second guy's orgasm came, and like his friend he removed his cock to decorate her behind with more strings of semen. He pulled out quickly, causing her to cry out in pain and surprise, then shot a large quantity of sperm all over her back and butt.

As this whole scenario was playing out, Aaron's climax suddenly came on. He didn't even have time to grab a tissue to catch it. His back arched and his dick jumped in Jeff's hand as a huge wad of cum shot out and hit him right in the face. He was so deep into his orgasm that he barely noticed that he had nailed himself. He was breathing deeply, gasping for breath as more shots of cum fired out and hit him on the chin and the chest.

As the climax died down, he became aware of a strong smell of semen, and then noticed that he had blobs of it oozing down his face. He flung his arm out to grab some tissues and wiped off as much of the warm, sticky liquid as he could. He looked down and saw puddles on his shirt starting to soak in, and a slow dribble oozing out of his pee hole. Truly, he had made quite a mess. He knew he should feel embarrassed at having done something so intimate and messy in front of Jeff, but he didn't really--because the whole thing had been initiated by Jeff.

Now he once again noticed Jeff's erect penis. It was much closer now--just a few feet away. Aaron couldn't help himself, and stared at it, comparing it to his own rapidly softening dick. Up close it seemed even bigger than it had from across the room. He felt an obligation to do for Jeff what he had done for him. He was afraid to put his hand on that big cock, but something underneath his conscious mind was pushing him to go ahead and touch it.

"Ca-can I do you?" Aaron stammered shakily, still woozy from his big climax.

In response, Jeff leaned back to give him clear access to his crotch. Well, that was it. He was going to have to follow through now. Since Aaron was right-handed and Jeff was sitting to his left, Aaron had to reach across his body while rotating his shoulders to the left in order to get his hand into Jeff's lap. He slowed down as it moved close to the erection, which seemed to be straining up to meet his hand. Eventually his fingertips touched the warm, smooth flesh of its underside, and Jeff gave a little moan of excitement.

Resolving to finish what he had started, Aaron closed his fingers around the shaft. It felt so warm, and he was surprised to find that he could not reach all the way around--in sharp contrast to holding his own dick. He felt a pang of envy and admiration for Jeff's endowment. Now he began slowly and gently running his grip up and down its length. He would start at the root with his fist buried in Jeff's copious bush, then bring it up to a point just below the head, then back down again. Jeff seemed to like this, giving little moans of encouragement.

Aaron was finding this whole exercise a little bit less awkward than he had thought it would be. The novelty of feeling another dick--and a big one--in his hand, and the realization that he was giving pleasure to someone that he considered to be one of his only friends, helped him feel somewhat more engaged in the project. He began to experiment with how fast he slid and how tightly he gripped the shaft, watching carefully to see which method provoked the most positive response from Jeff. He decided the thing to do was to slow down again, then gradually speed up and see if that got Jeff off.

Meanwhile the video was still going. The guys were once again double-teaming the girl. This time she was riding one of them reverse cowboy style while taking the other one in her mouth. As before, she was doing most of the movement, sliding most of the one guy's cock into her mouth as she raised herself up on the dick in her pussy, then moving her lips back to the head as she dropped back down onto the guy's crotch. Aaron noticed that she was still covered with sticky tracks of drying cum. It also occurred to him that the dick she was sucking was the one that had been up her ass previously, which shocked him. He felt his limp dick, which was still exposed and laying against his thigh, begin to harden and grow.

Jeff was starting to breath heavily and make little moans of excitement. Aaron realized that he was going to come quite soon, and wasn't quite sure what to do about it. He thought it would be weird to use a tissue to catch the ejaculation, but he was worried about the mess that would be made if he didn't. He increased the speed of his strokes, and kept his eye on Jeff's dick instead of the video. Meanwhile, his own dick was now almost completely erect again.

While he was dithering about how to handle Jeff's ejaculation, events took over. Aaron heard him make a loud sigh and felt his dick thicken with tension in his hand, then saw a large rope of cum shoot out the end. Aaron had been pointing Jeff's cock more or less straight up, and so the sperm launched up and came back down to land on Jeff's crotch and Aaron's hand. It made him flinch to feel Jeff's cum on his skin, but meanwhile the orgasm continued and five or six more blasts shot out. These also landed on Jeff's lap and Aaron's hand and arm. Finally a few dribbles came out and ran down the shaft to collect where Aaron's hand was touching it.

Knowing that Jeff's climax was finished, Aaron let go of his cock and grabbed a tissue to wipe off the cum that had landed on him. There was a lot of it! As he tried to wipe himself clean, he noticed that his erection was now rock-hard and straining as if seeking stimulation. While Jeff caught his breath and came the rest of the way down from his orgasm, Aaron began absently stroking himself, wondering if he might be able to get off a second time. Would that be weird?

Apparently Jeff didn't think so, because soon he sat up and pushed Aaron down so that he was reclining and began once again masturbating him. He paused and spit into his palm, then began again and now the slickness of his saliva allowed smoother movement. As he had when doing this by himself, Aaron closed his eyes and imagined that the girl from the video was sucking his dick. He felt his arousal growing, and now knew that he would be coming again soon. As he lay there, his fantasy of fellatio mutated and he pictured his hand sliding on Jeff's big dick. Then he imagined the cock ejaculating in his hand, and the feeling of warm cum landing on his skin. This thought process elevated his excitement to the level of imminent climax, and he began moaning uncontrollably. Jeff kept stroking and soon the wave of pleasure crashed on him and he felt his cock once again shooting multiple globs of semen. As before, it landed on his face and chest.

Aaron cleaned himself up, wiping as much of the cum on his shirt as he could. However, it had soaked in and he worried it would set and not come out. Jeff spoke up.

"Hey man, you should throw that shirt in my washer," he said. "I can loan you an old t-shirt."

"Yeah, that might be a good idea," Aaron agreed. He also thought he should take a shower since he reeked of sperm, and asked Jeff if he minded.

"No problem," Jeff said.

Aaron went into the bathroom in the basement and put on the shower, then stripped off his clothes and left them on the floor. He stepped in and pulled the curtain closed behind him. Then he heard the door open and sensed that Jeff was in the room with him.

"What's up?" he asked.

"You mind if I jump in with you?" Jeff asked. "I got a little messy."

Aaron did mind. He was weirded out by the idea of standing in the shower with another guy, but what could he say? It was Jeff's house, and they had just masturbated each other. What possible reason could he express for saying no?

He told Jeff it was fine and the curtain opened. Jeff stepped in behind him, and Aaron took note of the body hair on his chest and legs, very different from his own limited coverage. Aaron had rinsed his face, chest and arms, the places that had been directly nailed, and so he stepped back and let Jeff move into the water. Jeff quickly wet himself, focusing on his crotch. When he turned around to run the water on his back, Aaron was surprised to see that his dick was mostly erect again.

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