This Thing Called Life Ch. 07

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From roomies to friends with benefits.
3.9k words
4.65
19.3k
8

Part 7 of the 10 part series

Updated 10/05/2022
Created 05/26/2013
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I was having a dream about the ravishing I had taken from Mistress when I noticed two feelings that seemed too real for a dream, one, my ass was burning from the fucking I had taken but it was a good burn, and two my cock was achingly hard and it felt all the world like someone was stroking it.

I opened my eyes to a beautiful sight, my cock was being stroked by my beautiful friend Ashley, her other hand was on her own cock underneath her slutty skirt. And then I noticed I had been cleaned up but was still in Mistresses bed but she was nowhere to be seen and neither was Flavia who I was gaining feelings for.

"Wouldn't mind waking up this way all the time, someone taking care of my morning wood," I practically purred.

"Actually its afternoon wood," she countered, well played.

"What time is it?"

"Time for you to get to work," she said.

"After we finish of course," I pleaded.

"No silly, we're just friends, we can't play together anymore unless it's on the job, I was only playing with it a little because you were sleeping at full staff and it's impressive Jack, it is really special," she smiled and I lost my smile as she let go.

I started for the door totally naked and she looked questioningly at me but I quickly reminded her that I had no clothes to wear as Mistress had brought me up here naked. There were lots of looks and whistles as Ashley led me back to her room but unlike yesterday I had no problem with the ladies knowing who I had been with last night.

I used Ashley's shower while she pissed into the toilet next to me and I found that surprisingly erotic. While I showered she informed me that it was three in the afternoon so clearly that was some night last night. I filled her in on what had gone down in the room the night before and she jerked herself as I gave all the details and I found myself stroking too.

I stepped out of the shower and she pressed her body tight against mine, the feel of her big tits was great as usual but then my hand starting stroking her cock as she stroked mine, we were just a breath apart, breathing hard.

"Just friends right?" I asked.

She pulled away, gasped, flush face, and nodded.

"Friends without benefits Jack, you'll thank me when you need a true friend when you go through the process of becoming a girl," she said.

"I still haven't decided on that yet," I said.

"Then how come every time we mention it your dick responds," she said.

I looked down and sure enough it was bouncing up and down on its own, very hard and very in need. I started stroking.

"Besides, can you give up Misty?"

"Misty?" I asked.

"That's what we call Mistress when we are not in her bedroom. That was her sex room you saw not her sleeping room, still you must have made an impression if she let you sleep there. Most of us ladies can't how do we say 'accommodate her'."

"Well she made an impression in me," I offered reminiscing.

Then she threw a sexy black lace bra at me.

"What's this for?" I asked.

"It's a gift, you WILL be a little girl Jack, in some way you already are, but you have to hurry, your job is at the sex shop in half an hour," she said and waved goodbye as I rushed out the door, trying to get all my clothes on.

I arrived at the sex shop, hopefully in time but was confused when I saw the door had a closed sign on it. Several customers cursed as they tried the door then walked away. I was about to call Ashley when suddenly breasts were thrust into my open truck window.

"Hey handsome are you ready to earn some money?" Barbie asked.

She looked stunning in a formfitting red dress that stopped just below her ass and showed off her spectacular tits. She wore makeup to match and clearly wore wigs as her hair was bigger today than any other time I had seen her, she really was a doll.

"Thanks for coming on me last night?" was all I could think to say.

"My pleasure stud, believe me it was my pleasure."

She escorted me to the shop and made clear the shop wasn't closed to us, in fact the door buzzed open as we approached and I looked up to see a video camera. We entered and stretch was at the booth, he just nodded as Barbie led me to the booths in the back while I flashbacked to being taken by Tree. Barbie must have noticed.

"This is where Tree takes all of us the first time," she said.

"And how long before you..." I couldn't finish so I just grabbed at my nonexistent boobs.

"I was in the doctor's office the very next day," she said.

"Wow, were you gay before that?"

"No, I was a virgin, I'd never had sex with anyone but what happened back her in the booth, it all made sense and now this is who I am."

"You're beautiful," I stated the obvious.

She kissed me on the cheek and said "that's why my friend likes you". Then we heard the buzzer again and Barbie quickly told me the plan and shoved me into the big communal booth at the end and she went into the smaller one next to it. She urged me to hurry and I dropped my pants and put my cock through the glory hole. She gasped at my size even though she's seen it before and then I gasped as she took almost all of it down her throat. Barbie had mad skills.

As she sucked I heard voices at the end of the hall, they belonged to Eric who I had only known as Eager at the frat and his roommate Matt.

"Dude, it said closed so what are we doing here," Matt asked.

"I told you, it's open for us, I got us hooked up," Eric said.

"We both have girlfriends dude," Matt whined.

"You're the one who complains she doesn't suck you off enough. Just check this out and if you want to pussy out then you can," Eric countered.

And then as planned Eric opened the door to the smaller booth to reveal Barbie with her dress rolled down over her boobs so they were exposed as she sucked on my dick. Where she hid her cock I don't know but the boys would clearly see a woman.

"Holy shit!" Matt yelled clearly losing his wet blanket.

Matt reached over and fondled one of Barbie's boobs.

"Oh these are amazing, so much bigger than our girlfriends' tits," Matt said.

Barbie smiled but gently pushed his hand away per the plan.

"Sorry cowboy, I play through the wall only," and she closed and locked the door.

Then my door opened and there was Matt and Eric. Even before I started messing around with dudes I was able to tell when a guy was very good looking and Matt fit the bill. He was a tall, corn fed, jock type in perfect chiseled shape and he sported cargo shorts showing off his toned legs and a tee shirt that showed off a chiseled chest and powerful guns. But the strange thing that took me was Eric. Even though I'd been with him before, seeing him in his khakis and Hugo Boss shirt and the way he blushed when he saw me made me think how cute he looked, that was a first for me.

"What are we doing, he's not done, and I'm not gay!" Matt blurted.

"This is how you do it if you want your place in line," Eric said.

I moved quickly in the hope Matt wouldn't bolt; I pulled my dick out of the hole and faced the pair.

"Damn, the guy is fucking huge," Eric said, going off script.

"What are you gay dude," Matt said even though he was looking at me too. "Besides it's not that big," Matt said cocky.

"I'm getting too close; can one of you take over for a bit?" I said.

Eric couldn't get out of his pants fast enough. Matt looked shocked but finally let the door of the booth close. Eric made sure Matt got a glance of his already hard cock modest in size as it was and then Eric stuck his through the hole. And then did Eric fist bump me as he was getting his dick sucked by a T girl on the other side of the glory hole, why yes, yes he did. As I said he was cute, yeah I wanted another turn at him.

"Dude, seriously, she is so much better than Yuke," Eric said.

Apparently Yuke was Eric's girlfriend, Asian I presume. I stroked my cock to keep it hard and caught matt glancing more than once and something was rising in his cargo shorts and it looked impressive. I kept my distance, he wasn't ready yet.

"Oh man, she's deep throating me man, holy shit, oh fuck, I can't hold, oh, oh, ooooooohhhhh!!" Eric yelled and started slamming his crotch hard into the hole, his legs shaking and his face pressed sideways up against the wall in ecstasy. After a bit more shaking he finally pulled out grinning and his dick rock hard and glistening with sweat and cum.

"She swallows dude, does Jenny swallow?" Eric asked, referring to Matt's girlfriend apparently.

Matt also swallowed now, sweating, and then he shook his head no, so apparently Jenny does not swallow. He rushed to the glory hole and unzipped his shorts while trying to keep Eric's eyes away from his cock. But for show off reasons he gave me a quick flash and yes he could have been my twin in that department. I was suddenly impressed with myself. He fed it through and his reaction was instantaneous. Eric and I had both experienced oral from men or male to female women but clearly this was Matt's first time and his eyes went wide.

"Fuck no! Fuck no! How the fuck?"

"Told you she's good didn't I?"

He just shook his head and pressed harder against the wall.

"Oh like that, oh please, like that, oh fuck it's so fucking good!"

Suddenly Matt pulled all the way out of the hole. His dick was sticking hard through his zipper but clearly he felt constricted so he ripped his shorts and underwear off. Man he had some balls on him, they looked fruit sized and so suckable.

"Damn dude you're hung like Jack here!"

I shot Eric a look; he wasn't supposed to say he knew me.

"Do you mind if I call you Jack?" he recovered.

"Thanks bro," Matt said, not catching on, he was too busy putting his cock back through the hole.

"Oh my Gooooooodddd, oh baby will you marry me please?" Matt then asked through the wall.

"Thought you had a girlfriend," Barbie called from the other side, giggling.

Matt was frustrated as the sucking stopped and realized he caused it.

"I'm sorry, please keep sucking I won't talk no more," he begged and then moaned.

"Let me know when I can get back in dude," I asked for the reason of getting closer to him.

"Won't, unnnggh, be long, uh, oh for fuck's sake, long due, she is so good!"

And then I took my shot. I reached between his legs and cupped his balls with my one hand.

"What the fuck?" he yelled and stopped for a moment, just a moment.

"That's hot Matt," Eric said.

"Shut up, I'm not gay, Eric," he said but then shuddered under my touch and continued to thrust even harder into the wall.

"It's just guys looking out for each other, we do that here. She can't reach the balls through the hole so we guys help each other. I could stop, or you could have your friend do it instead." I said.

"No, you keep doing it, it does feel good, thanks bro," he said reestablishing apparently his, well... balls.

I traded a wink with Eric, we had him. For a few more minutes we watched as Matt swore like a sailor and did his best to break the wall down with his pelvis. He was actually crying a tear of joy out of one eye and was losing control of his breathing which meant he was close when suddenly he stopped altogether.

"What the fuck, why did you stop, I was about to come?" he yelled.

Matt pulled his cock out and looked through the hole.

"Sorry baby, my jaw needs a break, you're an awfully big boy you know," she said and before he could protest further she shoved a tube of lube through the glory hole.

Matt looked confused for a moment but Eric and I continued with the plan.

"Holy shit dude!" Eric yelled.

"What?" matt asked, slow on the uptake.

"You're in luck man, she wants you to fuck her" I offered.

Then he smiled and got it. He grabbed the lube and oiled his rock hard cock all over; he was impressive curved a bit to one side which kept him from being my exact dick twin. What he apparently hadn't realized through this was I still had hold of his balls this whole time, I just followed his motions so as not to cause discomfort so either he just hadn't noticed or he was enjoying it. Barbie urged him to fill her ass.

"Her ass, has your girlfriend ever let you fuck her ass?" Eric asked.

Matt said never and fed his dick through the hole. Barbie mewed encouragement, genuine I believe, she was enjoying what he had to offer.

"Fuck, I'm in, I'm all the way in her ass," he said in shock.

"Then fuck me with that big cock baby, it feels so good in my tight ass, do you like my tight as?" Barbie was calling through the wall.

"Fuck yeah baby, such a tight ass, I've never felt anything so tight, you're so fucking hot, please baby, marry the fuck out of me," he said and then we heard nothing intelligible from him for some time.

Matt was moaning and groaning, fucking the wall with all his might but you could tell he was getting frustrated with the wall being a barrier, he wanted to go even deeper. Barbie was doing her share of yelling and then she went off script.

"Oh baby, your fucking cock is going to make me cum, you want me to cum for you baby?" she yelled.

"Yeah baby, do that for me, come for me you hot piece of ass!"

"Aaaaahhhh, ohhh, ohhh, yessssss, fuck yeeeeeaaahhh," she screamed as he pounded harder.

I could only imagine the load she shot on the other side of the wall, I'm sure it looked hot. The loss of control seemed to return to matt and I could see he was near cumming and like clockwork on the plan, we heard the door next door burst open loudly and barber screech and then a large voice Matt didn't know belonged to Stretch yelled out.

"You fucking cunt, every time I go to work to pay the bills, you come her like a little slut, some on we're going home!"

We heard the door slam and footsteps. Matt pulled from the wall, fully raging in both hard on and face and rushed from the door. I grabbed him by the balls uncomfortably this time and he yelped and then shoved my hand away.

"What the fuck dude?"

"You don't have any clothes on and he's her husband so what can we do and they are gone already." I said.

"Fuck!" he yelled looking down at his raging boner. "I shouldn't have listened to you Eric!"

"But you said it was amazing," Eric pleaded.

"Yeah but you got off, I didn't, I'm horny as fuck, I've never been so horny. You guys get out, I need to jackoff," he yelled and started stroking right there.

"No offense but the money in the machine is mine and I haven't got off either," I said.

Matt finally noticed the screen running porn, a selection called 'Tranny Surprise'. In the current scene the surprise hadn't been revealed yet, it looked like a beautiful woman was giving a hot stud some great head. Matt started to come to his senses look around where he was and nodded in my direction like he got it and would leave but then...

"But there is one thing we could do," I said and Matt perked up, clearly interested.

"Yeah?" he asked.

"Make sure you understand I'm not gay either dude, but I've gotta have some release too, and you know what we said about guys helping each other out," I said, playing innocent and held up the lube.

"No way dude, you are not going to fuck me," he said.

"You'd be doing me, you win you're bigger than I am," I said.

I had stroked his ego but it might as well been his cock, it throbbed and danced on its own.

"It would help you get off too?" he asked still stroking his cock even as I stroked mine.

"My girlfriend plays around with me down there sometimes so I'll just think it's her and I'm sure something will happen, I'm so horny," I said.

"You have to leave Eric," he said as he approached my ass with his dick.

"No, it won't be as easy as it was with her, we need him to get you inside me," I said.

"Alright, fine, hurry up, I need to fuck something dude," Matt gulped.

Eric took his hard cock and guided it towards my ass. He stabbed the tip off the mark several times in order to get a feel for Matt's cock. If Matt caught on to what his friend was doing he didn't say a word but finally he hit the mark. Matt pushed in fast; luckily I had some practice last night. He appeared to be making up for the barrier earlier because he jammed as far as he could in my ass and pressed hard against my body then hugged me from behind.

"Aaah, dude, of fuck, you're even tighter than she was," he moaned.

I was worried he'd be a bull in a china shop right away but clearly he was enjoying being buried to the hilt in an ass. He held it there for just a bit and then slowly pulled back with a groan.

"So fucking tight, this is awesome!" he said.

"You're huge, but I can take it, you know you want to fuck," I moaned, ready for it.

Then he really went for it. He grabbed my hips and started pounding in and out, moaning and groaning and yelling throughout. I braced myself against the wall and took it like a bitch in heat, I was rock hard myself. Then suddenly he slapped one of my ass cheeks and I grunted in surprise. I could almost feel him redden behind me.

"Sorry Dude, I do that with my girlfriend," he apologized.

"You treat her like a little bitch," I asked.

"Yes," he groaned as he fucked even harder.

"Treat me like that," I offered.

Then slap again, it felt good.

"You like having your ass slapped bitch, you like this hard cock stuffed in your tight ass?"

"Yes, I love when you spank me," I offered.

"Oh I'm going to fuck you good you little slut bitch, I'm going to cum soon in your tight little ass," he said before becoming unintelligible for a little bit.

"Eric get over here," I said.

Eric came out from behind Matt, entirely naked now, half hard and holding the bottle of lube. He started to lube up my cock and then his ass. Matt slowed his movements.

"What the fuck Eric?" Matt asked.

Eric answered by standing in front of me against the wall and guided my rock hard cock into his ass. Eric took it like a pro and groaned until I was all the way inside him.

"Dude!" Matt yelled. "What the fuck?"

Eric was moaning too much to answer so I grabbed his shoulder to get his attention.

"Eric, tell Matt what you want to do," I said.

"Well we're roommates and we both complain about how our girlfriends don't put out enough, so sometimes we would jerk off in frustration at night when we thing the other is sleeping," Eric groaned.

"That's normal," Matt said and was getting off rhythm but certainly wasn't stopping.

"So I'd seen your cock before but recently things changed, and then the other night I stayed awake and listened to you jerk and I couldn't help myself so I jerked off the same time," Eric said.

"We're in college and shit happens, what's the point?" matt said frustrated.

"Tell him Eric," I urged.

"I ate my own cum wishing it was yours!"

There was dead silence, it was out there now but I noticed Matt picking up steam.

"He's getting harder in me Eric, keep going."

"I want to get into your bed and I want us to sixty nine, I want to suck your huge cock while you suck mine, I want to take every drop of your gorgeous cock in my mouth and then when you are still hard I want you to fuck my ass, I want to be a good little roommate to you when you're girl isn't treating you right," Eric got out.

"Fuck, oh shit, that's it, I'm going to cum, oh fuck, oh shiiiiittt..."

Quickly he dismounted and I pulled from Eric and Eric dropped to his knees.

"You want this you want this bitch? UUUUUUnnnnnnghghhhh..." Matt groaned and shook and spurted all over Eric's face.

"Here's more for you, here it comes, here I cum, ooooohhhhh yeeeeesssss!" I stroked it out and groaned.

My cum added to Matt's and suddenly Eric was squirting in his own hand. Matt quickly gathered his clothes and was quickly putting them on. Eric and I exchanged looks, now that it was over it was Matt's shame moment but then Matt tossed Eric's shirt at him.

"Hurry and clean up and get dressed we are going back to the apartment and do what you were talking about. And you're not moving out to the frat now, you're staying you got that bitch!" he yelled authoritatively.

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