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Pegged (again)

Pegged (again)

by Boogieman10469
11 min read
4.61 (6500 views)
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My new girlfriend (and cleaning lady), Conni and I had been seeing each other for just over 6 months, and we were having the time of our lives fucking each other crazy every chance we got. She had gotten especially adept at banging my ass with her strap-on, which she called "Domadora de culo" (the ass-tamer).

But she'd "tamed" me only 10 times since. She said she didn't want to 'do me' every time we had sex because she wanted me to miss it and crave it.

"It'll be like a 'special treat'..." she smiled.

Her method worked. Each time we got together, I craved for her to oil me up, spread my ass and fuck me raw. The teasing and the anticipation was driving me nuts. But about 3 weeks ago I got everything I wanted and more, when she invited one of her girlfriends over.

It turns out that I had actually "met" her friend, Joanna ("Jo-Jo"), several months before I'd hired Conni to clean my place. Jo-Jo is a bartender at a place I've been to a few times with my co-workers. I remembered once complimenting the floral tattoo-sleeve on her left arm.

"Bourbon on the rocks, with lime..." Jo-Jo said, recognizing me by my usual drink the night that Conni formally introduced us.

Jo-Jo's about my age, white with reddish-brown hair and freckles, and a little on the thick-side; a definite PAWG (she kinda looks like Sara Jay). She's also an East-Coaster - from Jersey. Conni's ex and her ex were old friends, which is how they knew each other.

We hung out at Conni's place that night, laughed and had drinks. I suspected that Jo-Jo was the other woman that she had previously mentioned, the one that she thought might be into pegging me too. I tried my best to play it cool and follow her lead, but I spent most of the night trying to hide my "woodie". My ass-hole tingled every time I thought about the possibility.

"So Conni tells me you like to sometimes play 'butt-boy'..." Jo-Jo finally said an hour and 3 or 4 drinks later.

I gave Conni 'a look'; she just smiled and shrugged.

"Yeah..." I finally replied. "I like to receive, but I can give my fair share too."

"That is so true..." Conni added, pressing her palm against the hard-on bulging in my jeans. "He got lots to give and loves to share..."

I had another innuendo ready, but Jo-Jo stopped me, came closer, kissed me and gave my hard-on a firm squeeze. Everything just escalated from there. Before I knew it I was on the couch with no pants, Conni knelt next to me sharing her breasts while Jo-Jo swallowed my cock.

Conni eventually stepped away and went to her bedroom. She returned proudly displaying a strap-on in each hand; her black "Domadora de culo" and it's (Caucasian flesh-colored) twin, which belonged to Jo-Jo.

"For you, papi..." she teased waving them at me. "The 'Ass-Tamer' and..."

"I call him 'Bam-Bam'...!" Jo-Jo finished the sentence coming up for air.

I felt a twinge of nervousness seeing how much they were enjoying this, but my dick got even harder and my ass-hole tingled again.

"We gonna take good care of you tonight, papi..." Conni assured me. She placed the dildos on the coffee table and climbed back onto the couch next to me. We kissed again and Jo-Jo went back to sucking me.

A few minutes later, our remaining articles of clothing were off and scattered around the living room. Conni tossed pillows from the couch on the floor and got down on all-fours.

"Gimme that dick, papi..." she smiled at me over her shoulder, "I need that dick in me now...!"

I knelt behind her and inserted myself. She was already soaking wet as I slowly started slapping my thighs against her delicious bubble-butt.

Jo-Jo knelt next to and kissed me.

"Save some dick for me, slut...!" she said to Conni, slapping her on her ass.

"Right now...it's all mines, mama..." she gasped, "All mines..."

I had secretly grown to love it when Conni talked about me 'possessively' like that: 'that's MY dick', 'that's MY ass'.

"Fuck her good..." Jo-Jo whispered in my ear. "Show me how you're gonna fuck me..."

Although I really didn't need the encouragement, I started banging Conni even harder.

"Ai, papi...!" she moaned. By the pitch of her voice I could tell she was going to cum soon. I slipped a damp finger into her into her ass-hole to push her along.

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"Oooh baby...you like it when he plays with that sweet, tight, little ass-hole, don't you..?" Jo-Jo was now laying next to Conni, kissing her and fondling her nipples.

Sweat glistened on Conni's back and dripped from her temples. Her back arched and toes curled.

"Mierda!" she screamed as the spasms took over and she collapsed into the pillows.

"My turn..." Jo-Jo grinned, spreading her legs and reaching for me.

I crawled over and mounted her. My cock was still wet with Conni's cum. We kissed and took our time getting used to each other before we found our rhythm and started really fucking. We were going at for a while, when Conni decided to join in. She spread my cheeks, poured lube down my ass-crack, and started fingering me.

"Wanna get you warmed up, papi..." she said with two fingers inside me.

My head was swimming. I could already imagine she and Jo-Jo ass fucking me.

"Oh fuck...!" I grunted seconds before I shot my load.

"Yeah, baby..." Jo-Jo moaned as she held me tighter. "Fill me up...give me all of it..."

We took a few minutes to catch our breathe and clean up. I was relaxing on the couch, when Conni approached me wearing 'the tamer'.

"Let's do this..." she smiled rubbing lube onto the dildo. She had me raise and spread my legs and spread more lube on my eager ass-hole. Then she held my ankles as she entered me.

"Yes..." I hissed through clenched teeth, savoring the sensation.

Conni liked to stroke me slow and steady and watch my reactions and facial expressions.

"I'm not done with you yet...!" Jo-Jo soon smiled as she stood on the couch and straddled my face. She firmly held the back of my head so that my mouth was pressed into her pussy.

"Eat that pussy, papi..." Conni encouraged me while slowly fucking my ass. I could already feel my hard-on returning.

It was hard to concentrate but I tried my best to focus on Jo-Jo's clit. I really needed her to cum so that I could get into what Conni was doing to my ass. It took about 7 minutes of my best pussy eating before Jo-Jo creamed all over my face.

"That was...fuckin' amazing..." she breathlessly complemented me while slowly lowering herself onto the couch covered in sweat.

I closed my eyes and fully gave in to Conni's ass-fucking. I was rock-hard again and slowly stroked myself as she stroked me.

"Oh baby, fuck that ass..." I moaned. "Fuck that ass..."

Conni smiled and spread my legs wider, pushing as deep into me as she could go - and holding it. I bit my lip as a tremor went through me that made my toes curl.

"That looks so fuckin' hot..." Jo-Jo said joining us again a few minutes later, wetting her fingers, rubbing and teasing my nipples. This gave me more tremors and chills.

I also noticed she was wearing 'Bam-Bam'. A few minutes later Jo-Jo lubed her dildo and knelt behind Conni, who was focused on me.

"Oh fuck..." Conni squealed when Jo-Jo slipped the strap-on inside; the expression on her face indicated that it went into her ass. I felt it too as she began thrusting me harder with each thrust she received.

"You like that, mama...?" Jo-Jo said, banging Conni's ass and pulling her hair. Conni only moaned in reply, closing her eyes and showing her best 'fuck me' face.

The whole scene was so beautiful and so fucking hot!

"Oh shit...!" I cried out as I suddenly, and unexpectedly shot my load over my stomach and chest.

I tapped out and went to clean up and left them to continue. When I returned from the washroom, Conni was spread-eagle, face down on the floor. Jo-Jo was on top, pounding her ass with everything she had.

Conni's eyes and teethed were clenched tight, her face showing an expression of both strain and joy. Her body seemed immobilized as her fingers dug into the carpet. She didn't (or couldn't) make a sound.

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Jo-Jo's expression also conveyed joy and strain, like she was enjoying an intense exercise. Sweat poured down her face.

I sat there and watched them. My dick was already getting hard again.

"No mas...I can't...I can't..." Conni finally gasped.

She'd had all she could take for the moment. Jo-Jo gave her a playful slap on her ass and raised off of my girlfriend. She immediately walked over to me with a wide grin.

"You ready for a good hard, ass-fuck...?" she asked waggling her toy in my face.

"How and where do you want me?" I replied. I was both turned-on and intimidated.

She told me to kneel in front of the large recliner. She wiped the dildo clean and applied more lube. Then she spread an ample amount to my still sensitive ass-hole as I spread my cheeks for her.

I took a deep breathe and let out a small 'squeal' when she pressed the tip against me. My involuntary reflex was to pull away.

"Where you goin', babe...?" Jo-Jo laughed, firmly gripping my shoulders. "I'm gonna give you what you've been askin' for...!"

She held me still as she slowly entered me. 'Bam-Bam' is the same length, but slightly thicker than 'Ass-Tamer". I gritted my teeth at took deep breathes until she was all the way in.

"Here we go, sweetie..." she announced as she slowly started stroking me.

I could completely understand the facial expressions that Conni was making before. Jo-Jo's technique is rougher by comparison, Conni's is 'smoother'. It took me a while to adjust, but once I did - Oh Fuck!

"You like being my 'butt-boy, huh...?" she said when she was full-on pounding me. Jo-Jo squatted behind me, firmly holding on to the arms of the recliner. Her thick thighs slapped loudly against my ass.

In that moment, she owned it.

Like Conni before, I couldn't answer, because I almost couldn't breathe. Tears welled up in my eyes and streamed down my face and the nerves in my legs tingled like I'd had an electric shock. I just gripped the chair cushion tightly, took it and enjoyed it.

Then Jo-Jo stopped and pulled out. The sudden new sensation almost made me cum. She instructed me to go over to the same spot where she'd fucked Conni earlier. I crawled unsteadily and waited on all-fours.

"I just love this hungry fuckin' ass-hole...!" she said kneeling behind me. She spread my cheeks, but this time she inserted her tongue. She proceeded to rim me and milk my cock, literally ass-fucking me with her mouth.

"Omifugingod...!" I moaned when I couldn't stand it anymore.

Jo-Jo pulled my cock backwards and sucked me like a vacuum cleaner on its highest setting. When she shoved 2-fingers into my ass-hole, the room got really bright, and I shot my load into her mouth. I think I actually...fainted.

The next thing I consciously remembered was laying face-down on the carpet, drooling and covered in sweat.

Back on the couch, Conni was exacting her 'revenge' on Jo-Jo, pounding the fuck out of her. I could tell from her screams and constant trash-talk that she was loving ever minute.

I was officially done for the evening, so I closed my eyes and fell asleep; I was sore, spent and exhausted. Conni woke me some time later and led me to her bed. Jo-Jo had left while I napped.

The next morning we compared notes while eating breakfast.

"Jo-Jo already text me that she can't wait to 'tag that ass' again...!" she shared, showing me the message on her phone.

"It's definitely gonna be a while..." I winced shifting on the pillow I'd placed on the chair. My ass was the most sore it had ever been and it took me a few days to fully recover.

"What do you think about a full-on 'fuck party'...?" Conni asked grinning. "Maybe 10 or 20 people...?"

I was in no condition to provide any real input so I sat and listened to her party plan. But by the end, I'd agreed to reserve a hotel suite, and I had a raging (sore) hard-on by the time I got home that night.

As I said before - 'be careful what you wish for, you just might get it'!

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