Office Affair

A Friend with benefits.

I shut down my computer and closed my file drawers. Another long week at the office was over.

My co-worker Jerry stuck his head in my door and said "TGIF, Sally. The gang is stopping for a drink. Will you join us?"

I hate the silly expression TGIF, but I was definitely ready for a cocktail.

"Sure, I will meet you at the bar."

Jerry is the office comedian, a real wise guy. He is liable to say anything; usually funny, sometimes over the edge. I thought about the time he went too far with Julie from accounting. She took time off, and when she returned to work it was obvious that she had breast implants put in.

She was pretty skinny with small breasts, but suddenly she had a rack. She was nonchalant about it; I suppose she thought that everyone would be polite. Not Jerry.

In the break room, in front of everybody, he just stared at her breasts.

"Hey, Julie. Those are nice. Are they new?"

She was humiliated, but I laughed along with Jerry and the whole crew. It was probably inappropriate, but I couldn't help myself. I just think he is funny.

I didn't take my briefcase or anything else from my office. I wasn't going to do any work this weekend, I had enough.

I didn't bother to drive; our favorite watering hole is just a short walk away.

I went into the bar, and the whole crew was already there with drinks in hand. There were about six of them, from several different departments. I won't bother to list their names, because it is not relevant.

I joined them at their table and ordered a glass of Chardonnay. It was very noisy in the bar, and even more so because there were several different conversations going on at the same time at our table.

Jerry was holding court as usual, telling jokes that were slightly vulgar but he always makes them funny. I didn't add much to the conversations; I mostly just listened and nodded my head yes or no.

I was on my second glass of wine when people began to stand up and say goodbye, and suddenly it was just Jerry and me left at the table.

We talked about how things were going at the office, just idle chatter and gossip. It was a little quieter now that the gang had left.

Jerry suddenly became very quiet and subdued, not his usual self.

"Jerry, what's up? Is it something I said?"

He answered "No, not at all. I was just thinking about something."

"Do you want to talk about it? You can tell me anything, you know. Let me help."

After a few minutes of awkward silence he finally spoke softly.

"Sally, if you spent the night at a friend's house, and woke up in the morning with your underpants down around your ankles and semen oozing out of your asshole; would you tell anyone about it?"

Oh my God, I thought, he has been raped!

How awful for him. If word gets out with our group in the office, he won't get sympathy he will get ridicule. The women are just as bad as the men; they will humiliate him beyond belief.

"No, Jerry. I wouldn't say a word to anyone."

His attitude instantly changed, and he said "That's great, Sally. Will you come home with me tonight?"

He was laughing so hard I thought he would fall out of his chair, and I realized that he had tricked me.

"You smart-ass! You had me believing you! Very funny!"

"Yeah, I got you good!" he said, still trying to stop laughing.

What he could not know is that I have had a strong fantasy wish to try anal sex for some time. Lately I have been watching internet porn scenes where some cute young girl takes a guy's huge cock up her ass and loves it. I usually masturbate and give myself an orgasm while I watch.

I fantasize that it is me in the video, and try to imagine what it feels like to have that long cock shoved up my ass. I put my middle finger up my ass, and that feels pretty tight, so I can imagine how a stiff, hard cock would stretch it open.

It's time to turn the tables on Jerry, and shock him for a change.

"I will on one condition. That you not tell anyone either."

That stopped him cold. I could see the wheels of thought turning in his head as he realized that I had just agreed to go home with him and let him fuck me up the ass. I just smiled at him and let it sink in.

He slowly began to grasp the fact that I meant what I said.

"Gee, Sally. What a pleasant surprise. Will you really come home with me tonight?"

"Like I said, on one condition. No one ever knows."

"Done deal!" he said, and threw down enough cash to cover our bar bill.

I left my car in the company lot where it would be safe, and I got in Jerry's car.

It was an awkward drive to his house. We both wondered if the other one really meant it. I stared out of my window while he concentrated on driving. Neither one of us said a word. I was certainly hoping that he understood me. I suppose if he just fucks me in the 'normal' way it will be OK. But it will be a big disappointment.

We arrived at Jerry's condominium and went inside. He poured us both a drink, which we didn't need or want. I moved closer to him, and he put his arms around me. We were not lovers, but we decided to act like we were. He kissed me and I kissed him back, and I reached down and touched the bulge in his pants.

That encouraged him, and he squeezed my butt with both hands. Our clothes almost flew off in a race to see who could get naked first. It was a tie.

I dropped to my knees and took his stiff cock into my mouth. I like to suck a guy's cock and make him cum in my mouth, and that would have been fine with me. But he stopped me, and helped me stand up. He reached around behind me and found my asshole hiding in my butt-crack.

"We have a deal, remember?" he said as he pushed his middle finger slowly up my ass. I had never had anything in there except my own finger, and his was much bigger than mine. He was not shy about it, he pushed it in all the way as I fondled and stroked his hard cock.

His cock was very nice, and stiff enough to do chin-ups on it. He was not qualified for the porn business, but it was by far the longest one I have personally experienced. I began to have second thoughts about taking it up my ass. At the same time I was tingling with anticipation about what it would be like.

We walked side-by-side into the bedroom, and he gestured towards the bed. I understood, and climbed onto the bed and lay face down. I spread my legs slightly and waited impatiently for my first ass-fucking. I almost blurted out "Just shove it up my ass and fuck me!" but I decided against it. Instead I said "Do we need something to help it go in?"

Jerry went into the bathroom and returned with a jar of Vaseline. I know you are not supposed to use it all the time because it is petroleum-based, but just once should be OK. And I knew I would need it to take his long meat-pole up my virgin asshole.

He stood by the side of the bed with his cock bobbing and swaying almost in my face.

"Sally, I want you to do this."

He handed me the Vaseline and moved even closer. I took a gob of it and began to put it on his cock. I coated the pink helmet-head and then the shaft, stroking it from the head to his balls. This aroused me even more because I was preparing his cock to go in me. It was like Anne Boleyn sharpening the axe that the executioner was going to use on her.

I guess he wanted more than my permission; he wanted me to be proactively involved. The lubrication allowed my hand to slide back and forth easily on his hard cock, and I knew he would cum all over my face if I didn't stop.

His cock had a solid, heavy feel to it that I loved. It was completely straight, with no upward curve or sideways bend. I probably would have been smarter to hook up with a guy with a smaller cock for my first anal adventure. But you never know what you are going to get until a man takes his clothes off.

I said "I think it's ready, but I don't know if I will be able to take it all. It's really long. Will you stop if I ask you to?"

"Yes. Of course."

I knew he was lying. You can't expect a man to stop when he has his cock half-way up your asshole. But it was too late to turn back now. I could only hope that he would show some consideration if I started to squirm and squeal.

I resumed my submissive face-down position, and he climbed onto the bed behind me. He fumbled a bit but finally got his legs outside of mine, hovering above me. The last vestige of modesty left me and I spread my butt cheeks so he could clearly see my asshole.

I felt the tip of his cock touch my anus, and a thrill went through me like electricity. After all of my fantasies, I was actually going to be sodomized.

I felt the pressure build as he began to push, and I tried to relax my asshole to help. I don't know if it really worked, but the head of his cock went into me. I let out a gasp as it stretched me to the max.

I don't make a lot of noise when I am being fucked, and I think the women who do are just acting, but this time I couldn't help it. I grunted like a wild animal as his cock forced my asshole open. Jerry stopped because he thought it was too much.

I whispered "It's OK. Don't stop."

The spasms subsided, and the tight ring of my anus just gave up and stopped resisting and relaxed. He resumed pushing and it slid into me gradually, just a little at a time. The Vaseline was helpful; I don't think it would have gone in without that.

I held still and kept quiet so he didn't think I was uncomfortable. I wasn't. I was in ecstasy. The feeling of his bare cock sliding up my ass was blissful, with the big head exploring and leading the way. I felt stretched and full of cock.

When I felt his wiry pubic hair press against me I knew it was all the way in. I swear I could feel every vein and wrinkle, and I could definitely feel the helmet-head somewhere in the vicinity of my belly button (on the inside!).

Words fail me when I try to describe how I felt. His cock was truly inside me; let me emphasize INSIDE ME! I wondered if when he began to thrust into me he would bump into one of my internal organs. I went limp with submission and arousal and anticipation; knowing that he was going to fuck me until he finished.

Jerry locked his feet around my ankles and held my shoulders with both hands as if he was preventing me from escaping. I had no intention of escaping. It felt different in my asshole than it does in my vagina. Even though they are right next to each other, your asshole is more private and intimate, and to allow a guy to shove his cock up in it caused some embarrassment and I felt my face blush.

I guess I was ashamed of myself for enjoying it so much. I hoped that he didn't run into anything gross, but if he does soap and water will take care of it.

Jerry has obviously done this before, because he was not embarrassed at all about being up my asshole. He began to slowly, methodically fuck me with a gentle rocking motion.

The head of a cock has always intrigued and aroused me, and I could feel it prodding and poking up against my soft insides. A cock is a magical thing, because if anything else was that far up my ass I would be screaming to get it out. My reaction to this was the opposite; I lifted my hips a little so it would go in the last fraction of an inch.

Jerry fucked me expertly with a steady rhythm, and the only sounds were our breathing and the creaking of the bed frame as we rocked it back and forth. Jerry concentrated like a man on a mission, and the sounds from the squeaky bed were as regular as a metronome keeping time.

I was completely submissive, just waiting for him to finish but wishing it would never end. I kept thinking about the tiny slit-hole at the tip of his cock where the precious semen would come out. I hoped he would stop with his cock all the way in when it happened. I didn't want it to gush back out of me; I wanted it all to stay in me.

Some women seem to think cum is just a smelly, messy by-product of sex. Not me, I want it in me, I need it and you could even say I crave it. If a man cums in my mouth I swallow it all, even though it has an unpleasant taste. Now the thought of receiving a load in my stomach from the other direction was very erotic.

My wait was over too soon, but when a man has to shoot his load he can't help it, it has to happen.

Jerry pressed tight against me and bellowed like a bull. I felt his cock throb and pulse, and spurt after spurt of cum squirted into me. I have never felt a man ejaculate that much, it just kept coming and coming. My body accepted it like a dry sponge accepts water.

I held still while Jerry pressed hard against me. A few moments passed and I wondered what was happening. Then I noticed that he was trembling and still holding his breath. I felt his cock twitch again and one more spurt of cum gushed into me forcefully.

I don't know if he always ejaculated like that or if he was aroused as much as I was. I imagine that it would be very exciting to a man to be the first to penetrate a woman's asshole.

I think a man enjoys introducing a woman to something new. Of course I am not some innocent young thing; I have had plenty of experience, just not in my ass.

Jerry collapsed on me and huffed and puffed as he tried to recover from his orgasm. I reached back between my legs and caressed and fondled his hairy ball-sack, and whispered "Thank you."

He replied "You're welcome."

I gave his balls a playful squeeze and said "I was thanking these, but thank you too."

He laughed and said "Why would you thank my balls?"

"Because they must have worked so hard to make that huge amount of semen. I thought I should express my thanks."

We both had to laugh at that, and he carefully pulled his still-hard cock out of me. When the head popped out my asshole felt stretched open, and I knew it would never be the same. We lay close together with our arms around each other and enjoyed the afterglow of good sex.

After about 30 minutes Jerry got up and went into the bathroom. I could hear the water running in the sink and I knew he was washing his cock. That was very considerate because I was thinking that I wanted to suck it again. But I didn't want to make him cum in my mouth; I wanted it up my ass again.

When he came out of the bathroom, I stopped him before he got on the bed and led him to the chair by the dresser. I indicated that I wanted him to sit down, and he complied. I kneeled between his legs and took his cock in my hand. It was soft, but not for long. Stroking it and taking it in my mouth did the trick, and soon it was hard and stiff.

I stood up and turned around, facing away from him. I reached back and spread my butt cheeks, and began to sit down slowly.

I said "Don't push, just aim." He lined it up perfectly, and as I lowered myself I felt the tip of his cock touch my anus. He did as I asked and didn't try to push it in. I kept lowering myself, as if I was just sitting down, and the head of his cock went up my asshole.

I continued taking it in me, just a little at a time. For just the second time in my life I felt the head of a cock finding its way up into my stomach. I don't know why I waited so long to try this; it was not the slightest bit uncomfortable. In fact it was more erotic and exciting than any other kind of sex I have experienced.

It was more than half-way in me when I stopped and fondled his balls for a moment. Then I continued sitting down as his stiff rod slid in deeper and deeper. The fact that I was full of his slippery cum helped, and soon I was sitting on his lap with his cock embedded in me. I let go of my butt cheeks and held onto the arms of the chair with both hands.

"Just hold still and let me do this."

I started to raise and lower myself, jacking him off with my asshole. The next time someone says to me "Go fuck yourself!" I can say that I know how to do it.

I lifted myself all the way up so that only the head of his cock was in me, and then lowered myself until every bit of it was up my ass. I kept that up with a slow, steady rhythm, up and down, in and out.

I whispered "Please warn me when you are about to cum. I want to make sure it is all the way in me."

Maybe I shouldn't have said that, because it was like throwing gasoline on a fire.

He made a whimpering groan and mumbled "Now!"

I sat down hard, making sure every last fraction of an inch of cock was in me. I felt his cock do its familiar twitches as his cum pumped through it on the way into me. He grunted like an animal as a fountain of cum shot into me. I reached down and stroked my clit and had an intense orgasm.

We just sat there for a few minutes with his hard cock inside of me. When I decided to get up, I lifted off of it, and when the head popped out a gusher of cum came out of me. It went all over his cock and his balls, and even made a small puddle on his right thigh.

I didn't want any of his huge load to go to waste, so I knelt down and licked up the puddle on his leg like a kitten laps up milk. I slid his cock in and out of my mouth despite the fact that it had just been up my asshole. I sucked it clean, and licked his hairy ball sack. I ignored the unpleasant taste and swallowed it. A man's cum stays alive for a while so I was literally eating him like a raw oyster.

I assume that I will also digest and absorb the quart and a half he injected up my ass. Sorry for the exaggeration, but Jerry does produce a lot of it. I gently fondled his balls, feeling each egg-shaped testicle carefully. If I were a cannibal I would eat these first.

For now, we were both satisfied and exhausted. We went to the bed and lay down together, and soon we dozed off.

I woke up with a start and looked at the clock on the nightstand. It was almost 11:30. I gently poked Jerry awake.

"Can you drive me back to my car? I need to get home and it is getting late."

Jerry replied "Why don't you just stay the night. No reason to go back out tonight."

I thought about it and decided it would be best. There is no one waiting for me at my apartment. And the thought of sucking Jerry off for breakfast was intriguing. If I am not too sore I might even ask him to fuck me in the ass again.

"OK, I will stay. Thanks. But remember, at the office we are just friends."

"Friends with benefits?"

"Yes, but that is between us. We don't need the gossip. No PDA. No bragging in the men's room."

I thought that this could be the perfect relationship. No romance, no drama. We could hook up every weekend. What am I thinking? I want to see him every night. I want his cock up my ass, I want to suck him off, I want him to eat my pussy. I want every ounce of jizz he can make inside me, one way or another.

Jerry fell asleep pretty quickly, no doubt exhausted. I rolled over on my stomach to stop the cum from oozing out of me. I didn't want to make a big wet spot, and even more important I didn't want to lose any of it. I told you that I crave cum. Soon I fell asleep too.