Ouch!! My Ass Burns !!!

11 Mar, 2020 | Erotic Stories

I started working as a legal intern, not even a junior attorney, at the law firm of Verbreennung, Stechen, and Wunderhintern in the fall after my graduation from law school.  The dress requirements were strict.  Women were to dress in a manner that emphasized their femininity.  I don’t mean slutty.  But the dress code emphasized dressing like a professional woman.

Women were to wear dresses or skirts and blouses.  No pants suits allowed here and high heels were required.  Hosiery was optional, and was recommended, but not pantyhose.  Only thigh highs or gartered stockings were acceptable.  If garters were worn, the guidelines stated that panties should be worn on the outside of the garters.

From the above rules, it was no surprise that the senior partners of Verbreennung, Stechen, and Wunderhintern, were not politically correct.  They were far from it.  The firm had been formed in the late nineteenth century by three immigrants from Germany whose successors kept the firm‘s name to the present day.  Hence their German surnames.

I was assigned to work with Mr. Verbreenung;  Mr. Walter Verbreennung.  Walter, as I will call him, was a dominant. I don’t mean a dominant in the BDSM sense of the word.  He was sexually dominant.   It didn’t take me long to discover why some of the dress guidelines were in place when I became his sexual submissive.

From the first day we met, I found Walter very attractive and sexy. His voice resonated in me, and the intensity of his eyes made me weak-kneed.

Like the other partners, Mr. Verbreennung worked long hours and required his staff to work the same hours.  That included me.  The difference was that I was essentially his personal assistant.  True, I did my portion of legal work for him, but I also took care of his personal desires and needs.   Including his sexual desires and needs.  For him, sex was a means of relieving stress.  I can’t remember how many times I was on my knees giving Mr. Verbreenung a blow job and being fucked on his desk, over his desk, on the couch or over the arm of the sofa in his office. I was more than glad to oblige his desires and really enjoyed our trysts.

Walter had been trying to get me to try anal sex for about six months after I started to work for him.  First, it was a casual question along the lines of, “What do you think?”

Although he was a dominant sexually, he didn’t immediately force himself on me.  I had told him I was an anal virgin and I didn’t think I’d like it. When he would ask, “Why?” I would tell him that most of what I had heard from other girls that I knew was negative and that I really didn’t believe websites that stated things like, “If it hurts, it’s being done wrong.”

Walter kept telling me he loved my long legs and tight butt and promised me that someday  I would get his cock up my ass. He kept increasing the pressure for me to submit.  To put it bluntly, Walter didn’t like the word no.  

More recently it had become more of, “I really need for you to let me fuck you in the ass, Meagan.”

What didn’t help his cause was that Walter was endowed with a much larger cock than normal; eight inches long and nearly two inches thick.  Even vaginally it hurt from time to time, usually when he gave my pussy a hard, fast pounding.

One evening, as we were eating a late dinner at one of the local restaurants near the firm’s offices, Walter brought up the topic of anal sex again.  Usually, we ate dinner in the office ordering food in.  Tonight, though, was different.  It was our one year anniversary of working together.  Walter had said he wanted it to be a special occasion.  I soon discovered what he meant by “special occasion.”

“Meagan,” he started,  “I know your ideas about anal sex. I know you’re an anal virgin. I want that anal virginity.  Do you understand what I’m saying?  I want that virgin ass of your!”

I could tell from his tone that this conversation was on a different level than the previous talks we had had about anal sex.
“I know you’re afraid,” he continued.  “But you’re a grown woman, and I want to you start taking it in the ass like a woman.  I want you to take it in the ass for me, honey.”

I should admit at this point, that though I had resisted him to date, I had talked with other women interns in the firm.   It seems that all the partners routinely practiced anal sex on the interns that worked for them.  I discovered that I was the only anal virgin left in the firm!  

I also found out that while their first attempts at receiving anal sex were definitely quite painful, they admitted that it did get better once they learned to fully relax instead of fighting the cock.   They also told me they were able to experience some incredibly intense and powerful orgasms from anal sex after they started getting fucked in the ass on a regular basis.  That certainly got my attention!

After listening to Walter, I acquiesced. “If I let you take my anal virginity, will you be gentle with me?” I asked innocently.

“Meagan,” Walter started to reply, “That’s an immature attitude.  When I fuck you in the ass, it’s going to hurt.  Most girls, most women whose anal virginities I’ve taken, have cried or sobbed during the experience. There is no way to avoid it. Meagan, losing your anal virginity is going to hurt.  It’s not going to physically injure you, but you will find you probably won’t be able to walk or sit down on your ass comfortably afterward for a couple of days.  At least that’s been my experience.”

“You mean I’m not the first anal virgin you’ve taken, Walter?”

“No, I’ve had three others before you.  They walked out of the office after their butt fuckings and you will too.”

I bit my lip, somewhat nervous and afraid I will admit.  “Alright, I will let you fuck me in the ass.  My place or yours?” I asked.

“Neither,” Walter replied.  “I want to fuck your virgin ass in my office, bent over my desk.  But first, we need to stop at the pharmacy and get something we’re going to need.”

After paying the bill for dinner, we started to walk hand-in-hand towards the pharmacy just a few blocks down the street.  I have to admit that although I agreed to let him ‘deflower’ my butt,  I was afraid and told him so.  He gently squeezed my hand in response.

“There’s nothing to be afraid of Meagan.  It’s natural to be nervous and apprehensive, but there’s nothing to be afraid of.  After it’s over, you’ll be glad you took it in the ass.  Trust me.”

Upon entering the pharmacy, we walked to the aisle labeled “Sexual Products.”  We walked past the condoms.
“We don’t need those?”  I asked.  As I said, I wasn’t entirely ignorant about anal and practically every website that I visited emphasized the need for condoms.

“No, Meagan, we don’t,”  said Walter.  “I’m going to shoot my load in that tight little butt of yours.”  He let out a little laugh as he was saying it.

Once we got to the lubricant section, Walter carefully scanned the shelves. “We’re looking for ‘Astroglide’,” he said.  “In my experience, it provides optimum lubrication for anal sex.”

Picking up four tubes of the lubricant, we proceeded to the checkout counter.  The clerk scanned the tubes; “$5.79, $5.79, $5.79, 5.79,” she said.  “That’s $24.90 total,“ the clerk said. “Looks like you two are going to enjoy yourselves tonight,” she added smiling.

“Meagan is going to get her ass fucked for the first time soon, Robin,” Walter replied, swiping his credit card at the same time.

“You know her?” I asked.

“Oh yes, quite well actually. To be honest, I took her anal virginity several years ago.  As you can see, it didn’t kill her taking me in her ass.  It’s not going to kill you either Meagan.”

It was now quite late at night, after 10:30 P.M.  Entering the firm’s office building, it was dark and except for the guard at the entrance desk, deserted.

“Good evening Mr. Verbrennung, Miss Meagan,” the guard said as Walter led me by the hand to the elevators.

“Good evening George,” Walter said.  “Miss Meagan and I have some unfinished business that needs to be taken care of.”

The elevator doors opened, and we walked in.  Walter pushed the bottom for the 10th floor.  Walter kept holding my hand and noticed that my breathing was quickening and I swear could hear my heart pounding.

“Relax Meagan.  Just follow my instructions and let it happen.  We’ll get through this together.  Tonight’s a big night for you.  You’re going to become a complete woman sexually.”

As he finished, the elevator door opened and he squeezed my hand even tighter. We walked down the hall to his corner office.  Swiping his access card, the door ‘clicked’ open, and Walter pushed open the door for me. “After you,” he said.

As I entered my nervousness increased. “What have I agreed to?” I asked myself.  I wanted to do this but was definitely very apprehensive about what was to come.  I bit my lip and allowed Walter to lead me to the inner office.  Again he swiped his access card and door ‘clicked’ open.

Walking in, he turned on the lights near the sofa but left the overhead lights off.  I walked over to the large glass windows that gave a spectacular view of the city lights down below.  As I was viewing the scene, Walter proceeded to his desk.
Clearing his desk, I watched as he opened two of the tubes of Astroglide and placed them on the edge of the desk.

Walking behind me, he pulled me close and whispered in my ear “I want your anal virginity.  I want your ass.”

I turned at his words and gazing intently into his eyes, our lips moved closer and closer together until they met. My tongue began to twirl inside his mouth, exciting our passions.  I could feel his hand behind me, sliding down to my skirt and squeezing my butt as he pulled me tight into him.  My tongue danced in his mouth, and both of us were getting extremely excited.  We could hardly restrain ourselves now.

Walter broke our kiss and moved behind me, pulling me tightly into him as he began to caress my breasts through my blouse. I could feel his huge, stiff cock pressing against my ass.

I gasped loudly “It’s so big.”

“Yes, Meagan, it’s big,” he replied.

He began unbuttoning my blouse and slipping his hand inside to cup my breasts through my bra. “It’s long, and it’s thick, and it’s going in your virgin ass in a few minutes.  Would you like that, Meagan?  Would you like to feel your tight virgin ass getting split apart by my cock?”

 “Yes,” I whimpered softly.

“Do you want to see what you’re going to be taking up your ass?” He asked.

“Yes,” I whimpered again.  “Show me.”

“First,” Walter started, “I want you to take your blouse and bra off.  Show me your breasts.”

I nervously yet eagerly finished unbuttoning my blouse.  I knew there was no going back now.  As I slid it off my shoulders, I placed it on one of the big chairs that faced the couch.

Walter moved and squeezed each breast eagerly and firmly.  I gasped loudly.  Suddenly he pinched my nipples.  I gasped even louder.

“That’s it,” Walter said.  “Just relax and let it happen.”

He began suckling on each breast, concentrating on the nipples.  I started purring softly.  I grabbed his head and ran my fingers through his hair. “Yes,” I whimpered, “Oh yes!  That’s it, suck my titties.”

 I could barely restrain myself now.  I reached down and slid my hand down his trousers taking his hard, stiff cock between my fingers.  His cock reacted to my touch by giving a jerk which brought a smile to my lips.  After a few more moments, Walter pulled away and went to the desk.  Taking his shirt and tie off, he placed them on the chair with my blouse and bra.

He motioned to me to join him.  As I walked over to him, I traced my fingers down his bare chest and then began kissing him again.  Again, he broke the kiss.“Get on your knees, Meagan.  I want you to see you what you’re going to be taking in your ass in a few minutes.”

Nervously, I slid down to my knees.  My heart was pounding hard now.

“Unzip me.  Suck my cock.,” Walter commanded.  “Get it good and hard for your tight virgin ass.”

I did as he asked.  His huge cock was fully erect.  As I freed it from his pants and undershorts, it sprang forth like a monster. Grabbing it in my hand, I started twirling my tongue around the head.  Precum was seeping from the tip, and I eagerly tasted his saltiness.

“That’s it. That’s it,”  Walter moaned. “Now put it in your mouth. Suck it, Meagan.”

I did as he ordered and eagerly began moving his cock in and out of my mouth. As I did, he reached behind my head and guided my mouth onto his cock.

Walter’s speech was slurred by his increasing moans of pleasure.  “Oh yes, that’s it, suck it good.  See how long it is Meagan.  See how thick it is.  Think about how good it is good it is going to feel when I ram it up your virgin ass.”

His remarks only heightened my nervousness about what would come. I continued to eagerly suck his cock, eliciting more precum.  I started to nibble on the shaft as I caressed his balls.

“Yes! That’s it. Suck it!  Don’t stop!” Walter ordered.

His actions were becoming uncontrollable.

  He began trying to force it deeper into my mouth, and I started to gag.  Walter relented.
“I’ll have to teach you deep throating,”  Walter moaned.  “But not tonight.  Tonight I have other plans for you.”
After several more minutes of sucking his cock, Walter asked me.  “Are you ready to take it like you’ve never taken it before? Are you ready to take it where you’ve never taken it before?”

Nervously, I responded, “Yes.”

He looked down at me, brushing the hair away from my face.  “I think you are,” he said.  “Stand Up!” he ordered in a commanding tone.

Fearfully, I did as he asked.  Again he brushed my hair from my face and kissed me gently on the forehead. “Relax,” he said.  “Just do what I tell you.”

“I will,” I told him.

He led me to the other side of his desk.   “Meagan!” He said in a commanding tone.  “I want you to unzip your skirt!  Unzip your skirt and let it fall to the floor.”

I hesitated for a few moments.  “I’m scared,” I whimpered.

“Don’t be scared.  I told you, there’s nothing to be scared of.  Unzip your skirt!”  He waited for just a moment, then in a commanding voice  ordered, “Unzip it now!”

I slowly reached behind and began to unzip my skirt.  My heart was pounding.  It felt like it was going to leap from my chest.  My breathing quickened, became shallow.  I reached the bottom of the zipper track.

“Let it fall to the floor,” Walter directed.

Releasing my skirt, it slid off my hips and landed in a soft ‘whoosh’ on the floor around my ankles.
He moved around me, eying my body. “Mmmm,” he commented, As His eyes took in my lingerie; Ivory lace panties outside of a matching ivory lace garter belt, holding up the nude-colored sheer nylon stockings.

“Very nice.” “Very nice indeed. Your garters will frame you ass nicely as I take your anal virginity and fuck you in the ass!”
I could detect Walter’s palpable enthusiasm and his excitement, and I bit my lip in expectation of what would come next.
“Now Meagan,” Walter began.  “Take your panties down and step out of them.  Bare your butt for me because you’re going to get fucked in the ass.”

I had resigned myself to what was about happen. Sliding my hands down to the waistband of my thong panties, I slowly slid them down my legs.  I then stood back up, wearing only my garter belt, stockings, and high heels.

“Step out of your panties,” He ordered.  I did as he requested and he reached out with his hand.  I offered him mine.  He then led to the front of his desk. In a soft voice, he told me “Now, be a good girl and bend over my desk.  Show me your butt so I can fuck you in the ass.”  As he told me those words, I felt his hand on my shoulders, gently but firmly ‘forcing’ me to bend over the edge of his desk.  I could see him pick up a tube of the Astroglide in my peripheral vision.  Unscrewing the cap, I felt him squeeze a large amount of the lube down the crack of my butt.  I gasped as I felt the coldness of the lube.

“Just relax your butt,” he said.

“It’s kind of cold” I answered back.

“Don’t worry Meagan,”  Walter replied.  “In a few moments, your little butt will feel as if it is on fire.”

Suddenly, I tensed up as he slid a finger into my butthole, forcing the lube inside and coating the inside of my sphincter.  I began moaning as he slowly slid his finger back and forth, coating the rim of not only my sphincter but also deeper inside my anal passage. He picked up the bottle again and squeezed more of the lube down the crack of my butt.  Again I felt his fingers, not just one this time but two and then three.  I moaned again.  His fingers felt good, very good.  I felt myself relaxing as I felt him move his fingers slowly back and forth, spreading the Astroglide liberally. 

I was so relaxed from his fingers that it took me a few moments to realize that they were no longer inside of me.  Turning my head and looking over my shoulders, I could see Walter squirting the lubricant on his long, thick cock and coating the entire length with his fingers.   When he was finished, he moved behind me.

“Reach back and spread your cheeks!” He ordered.

Nervously, I did as Walter said.

“Now you listen to me!” Walter began in low but firm and commanding tone.  “I’m going to take your anal virginity.  It is going to hurt quite a bit.  I want you to hold still and take the cock in your ass like a big girl.  Show me how a big girl loses her anal virginity.”
Suddenly, I felt his cock as he rubbed up and down the length of my butt crack before centering it against my sphincter.  I instinctively tensed up.

“Don’t tense up!” Walter commanded firmly.  “If you fight my cock, it’s only going to hurt more.  Just relax your butt.  Take it in the ass like a big girl.”

Walter began to press against my sphincter.  I grabbed my butt cheeks with clenched fists as he started ‘forcing open’ my sphincter.

“Ouch,” I whimpered.  “Please, it hurts.  Be gentle.”

“I know it hurts,” Walter replied.   “That’s normal.  Just relax and let it happen.  Don’t fight it.”

He continued the pressure against my butt hole.  Suddenly my sphincter opened up to admit his monster.   I experienced burning, searing pain that surged through my body.

I arched my back and screamed out in “OOUUCCHHH” as his cock entered my butt.  My breathing became shallow and quick.

“Breath!” I could hear Walter tell me.  “Breath and relax your butt for me.” He held still for several seconds until the initial wave of pain passed.  When he felt me relax a bit, he grabbed my hips and began to ‘force’ his cock deeper into my butt.

I squeezed my cheeks with clenched fists again and whimpered soft “ouches” in between gasps and moans.  “Please!  You’re tearing my ass open,” I whimpered.  “Please you’re splitting me apart,” I said as I continued to whimper “ouches” as he went deeper. “Please,” I begged.  “It burns!  It stings.!  Please, be gentle.”

“I know it’s hurting.  That’s normal.  Just relax your butt.”

“Please, I can’t take it,”  I replied  “Please!”

Walter tried to encourage me.  “You can take it. You’ve taken four inches up your ass so far.  You need to take all eight inches up your ass.  Don’t fight it.  Relax your ass; take it all the way up your ass like a big girl.”  He continued to push his cock deeper and deeper into my butt.  Inch by inch his cock was ‘destroying’ my anal virginity.  Inch by inch his cock was ‘deflowering ‘my virgin ass.
I bit my lip and began to softly weep as the burning, stinging pain increased and began to overwhelm me.

“It’s all right, Meagan,” Walter told me as he continued to try and verbally encourage and support me.   “You’re taking it so well.  Such a big girl taking it in the ass.  Just another inch and it will be all the way in you.”

Suddenly, he gave a strong, powerful forward thrust, ‘forcing’ the remaining inch up my ass.
I screamed out loudly, “OOOUUUCCCHHH!” as I arched my back.  I tried to push him back with my hands, but he pushed them away.

“Keep your hands away from your butt,”  he commanded.  “Just relax. It’s all the way in your ass now.  You’re no longer an anal virgin,” he told me.

He held still for a minute or so, giving my butt time to get used to its intruder and giving me time for my breathing to return to normal. “That’s it, Meagan,” Walter said.  “Just relax and get used to the cock in your ass.  See how good it feels.  See how it fills your tight little butt.”

By now I had lost all track of time, but I later learned from him that only about three minutes had elapsed from the moment he began to put his cock in my butt until I had taken the entire length.

As soon as felt me relax, he pulled his cock back until just the head remained in the butt.  I gasped loudly as I felt the pressure and to a large extent, the pain, lessen.  He held still for several moments, allowing me to get used to the new feelings.
Suddenly, unexpectedly and without warning, he grabbed my hips slid his massive cock back up my ass.  I gasped and screamed out, “OOUUCCHHHH!” loudly again.

“Relax your butt, I’m going to fuck your ass now.  Just relax and take your buttfucking like a big girl.”

Again,  he waited for just a moment before pulling back again and then, sliding it back into my butt; this time a little bit quicker than the first time.  Again an intense burning, stinging sensation overwhelmed me.  Pulling back again, he plunged it back into my ass for the third time.  Then for a fourth time.  And then a fifth time.  And a sixth.  Each time I let out “ouches,” the loudness and intensity of which varied.  These were interspersed with more pleasurable sounding moans and gasps as he starting buttfucking me with a regular rhythm.  Although it still was hurting, the sharpness and intensity of the pain began to lessen.  I found myself able to relax somewhat as he continued to fuck me in the ass.

Walter could feel me relax and began buttfucking me a little faster and a little harder, the pain increasing
“That’s it, you’re taking it in the ass so good.”   He told me again, “Such a big girl taking in her ass.”

“Please, slow down” I gasped.  “Give me time.”

Walter continued his thrusts. “The faster and harder I fuck you in the ass, the quicker I’ll cum and shoot my load in you,” he told me.  “Just relax your butt while I fuck you in the ass.  You want me to cum in your ass, don’t you?  You want to me shoot my hot load in your butt don’t you ?”

“Yes!” I replied.  “Fuck me in the ass until you cum!”

He began to pick up the pace and strength of his thrusts.  My ass was on fire.  I started to sob heavily as the burning and stinging overwhelmed me.

“That’s it, just a little bit longer,” he said as he began ramming his hard cock into my butt without mercy.

I began to scream, “OOUUCCHH,” “OOUUCCHH,” OOUUCHH” he quickened the pace of his thrusts.  I could hear his balls slapping against my butt with each forward thrust; I could feel my butt cheeks reverberating from the pounding.   My sobs and my “ouches” were filling the office.

“That’s it, take it!  Take it hard!” Suddenly and unexpectedly, Walter gave a hard forward thrust burying cock deep in my ass.
As he did, I could hear his loud “AAARRRGGGHHH” then his yell of, “I’m cumming!  I’m cumming!”

As I felt his last powerful thrust, I screamed out “OUCH” again and then as he came, my own “AAARRRGGGHHH,” exploded out of my mouth.

Within in few moments, I could feel his cock shrivel up and slip out of my ass.  I remained bent over his desk; out of breath, gasping for air.  Gradually my breathing and heart rate became more regular and, after several minute recuperating, I was able to stand.
Suddenly, I felt his warm, sticky seed oozing out of my butt.

He quickly handed me a towel and washcloth from his private bathroom.   The warm washcloth especially felt good on my sore, tender butt hole.

“Meagan, that was fantastic.  You took in the ass so good.  Just like the big girl you are.  Now you’re truly a complete woman.”
He then asked me a few questions.“So what do you think of your anal experience?  Think you’ll want to do this again?”

I answered “I don’t know.  Give me time.”  My butt was still stinging and burning, although not as much as when he was buttfucking me.  I reached back, rubbing my sore, tender butt.

He then asked, “Did it hurt as much as you thought it would?”

“More,” I replied, “A lot more, especially at first.  It hurt so bad.”

“That’s normal.  The first time is the hardest.  I have to tell you though; you were such a big girl about it.  I can’t tell you how well you took it and how good it felt fucking your tight ass.”

Walter then went to his office refrigerator and brought out a bottle of wine and two glasses.“Let’s celebrate the loss of your anal virginity tonight, Meagan.”

After emptying the wine, both of us eventually both went home.  When I got to my apartment, I took a hot shower and then collapsed into a deep sleep.  The day had been exhausting for me.

Monday morning, when I got back to work, it seemed that all of the other women in the firm could sense a difference.
When I took my place in Walter’s outer office, he came out and asked me “How does your ass feel today, Meagan?”

“It’s still a bit sore and tender,” I told him, lifting myself up and rubbing my butt.

“Well I have a solution to that problem,” he replied.  “How about another anal lesson tonight.”

“Tonight?” I asked.

“Tonight,” he said in a commanding tone again

Knowing what I was in for, I swallowed hard before replying.  “Tonight then” I answered.

“By the way, Meagan, do you know what my surname means in German?” Walter asked.

“No, I don’t” I replied, thinking to myself that I probably should have used some initiative earlier and found out the answer to that question.

“Burning,” he replied with a chuckle.

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