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Try, Try Again

Posted by: Author: Age: 28 Posted on: 3 comments
7 likes 842 views Category: Masturbation Female-Male Tags: Mom


After my roommate moved out, I lived alone for about a month before I realized I couldn't possibly keep paying the rent.

I placed an ad for another girl, but I only got a few takers and they were pretty high maintenance. I placed another ad in the free weekly newspaper for a girl or guy and I found the perfect roomie.

Sean was cute, neat and I was pretty sure he was gay from his blonde, skinny, hairless body and his very gentle mannerisms. He had long fingers and bony arms and he always seemed shy around me. I didn't ask him right away, but I just figured it was a secret and he didn't want to talk about it. He was from a strict Catholic family, so I didn't press the issue and anyway we both worked a lot of hours.

About four weeks in, I came home from a party around 2am and stumbled into the living room and passed out on the couch. I awoke at about 5am to the sound of Sean moaning and saying, 'Oh, yes, touch me, touch me...'

Whoa. Was somebody in there with him? I looked around for coats, hats, shoes, anything, nothing was there, and I didn't hear any other voices, either.

If I had been in my room at the other end of the hall, I would never have heard it, but he was definitely jacking off and talking quietly to himself. I held my breath and listened as he finished with a groan and a slapping sound.

I was kind of grossed out, but also kind of turned on. I get really horny right before my period, and this was that time. I tiptoed to my room and closed the door so it wouldn't click and touched myself silently until I fell back asleep.

Spring came about two weeks later and we decided to go for a run to wear off our winter fat. It was the first time I'd seen Sean wearing shorts. He had such scrawny, bony legs I almost felt bad for him. It didn't seem like he'd have much luck getting a guy as shy and skinny as he was.

Then I noticed his cock.

His running shorts were thin and wispy and he must have been wearing boxers, because his dick was totally obvious and semi-hard. I hadn't had a boyfriend in three months and I was getting to the point where I was masturbating almost every day in the shower, so even though Sean didn't really turn me on, seeing such a big cock on such a scrawny man just got me going.

I tried not to look while we were jogging, but I kept seeing him bouncing up and down and it really started to turn me on. Now I was the one feeling awkward, with the tingling in my clit starting as we were stretching in front of the building, and sort of 'accidentally' bending over in front of him to stretch my calves to see if I could get a response. I am athletic and definitely not petite, but I've got a nice shaped bum, and guys always seem to appreciate it.

Still thick and semi-soft. No obvious response.

When we got upstairs, I tried again: 'That really got my blood pumping,' I said. 'Thanks for pumping me up.' I looked at his eyes and he chuckled nervously.

Nothing. Damn it.

In the shower, I made myself climax three times with the spray head on pulse until I thought I could calm down without jumping my roommate. I couldn't figure out why I was getting so turned on by this effeminate guy I would never ordinarily be attracted to.

We turned on golf and sat on the couch that afternoon and he was wearing a pair of cut-off sweat pants. Once again, I saw that massive cock clearly through the fabric.

I decided to just bring it up.

'Dude,' I said, 'I think I can see your thing.'

Sean got really embarrassed and covered himself with a pillow, blushing pink in the cheeks. 'Sorry!' he exclaimed, looking genuinely uncomfortable.

'No, I'm not trying to call you out,' I said, 'but you are a lucky man from the looks of it.'

Sean was now slouched over the pillow on his lap, looking miserable, and I was starting to get crazily aroused making him wither in front of me.

'I hope that wasn't too direct,' I said. 'Just trying to pay you a compliment.'

'Thank you,' he said. He didn't sound very grateful. He sounded nervous.

'You don't have to cover it up,' I offered, trying to put him at ease.

'Um,' he said. 'I think I do now.'

I don't know what came over me, but I got pissed off that he was being so lame, and I ripped the cushion out of his hands and off his lap and, oh my god.

He was now fully erect, maybe seven or eight inches long and as thick as a roll of cookie dough, standing straight up in his shorts so that the waistband was pulled away from his skinny waist.

I have never seen a cock that big before or since. The sweatpants were so tented out that I could see his big balls through his leg.

Sean got up and rushed to his room showing me his enormous cock unmistakably through the fabric as he slouched hurriedly off. My clit was now tingling like it might soon break if I didn't touch it, but my heart was pounding at how weird he was being and how suddenly he'd just run away.

If I hadn't been so horny, I probably wouldn't have gone to his room, but I did and I knocked once and opened the door before he could answer so I could apologize.

Sean was sitting on the edge of his bed with his shirt off, bird chest showing, trembling. He didn't say anything as I came in and knelt down between his legs and ran my hands up and down his still-stiff, monster cock.

'Can I?' I asked. He nodded meekly.

I pulled him out and he sighed when my fingers touched his soft, bumpy skin. He was angled up towards the ceiling and wet at the tip. I rolled him in my hands, he was so thick I couldn't even grip him totally, marveling at this thing that my skinny, possibly gay roomie had been hiding in his pants.

I cupped his enormous balls as I slid my fingers up and down that cock a few times and Sean started moaning like I'd heard that night on the living room couch and saying, 'oh yes, oh yes, oh yes, touch it.'

I think I set him off by tickling the back of his ballsack and I gripped him tighter and stroked as fast as I could and he just started shooting straight up into the air so that it went up and came down all over my blouse and skirt and some of it got in my hair. I've seen some guys go off in spurts before, but never so much at any one time. He looked like he was almost crying as his little hips fucked out and he thrust his enormous cock into my hand to milk it all out of him...

It was the start of a very nice friendship.



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