Pegged
Be careful what you wish for -- you just might get it.
And if what you wish for is to be ass-fucked by your house keeper with an 8-inch strap-on...whoa, baby!
But to be truthful, I loved every minute and every inch.
My name is Gerald. I'm a single, financially well-off, middle-aged, Black professional living in what I consider to be the ass-crack of America -- the Midwest. Contractual obligations have me stuck here for the next 3-years. But the money is too good to pass up, so I endure.
I am happily bisexual. I love a good stiff cock just as much as I enjoy a sweet, wet pussy. Unfortunately the opportunities to experience both when, where and how I like are extremely limited in the small town where I currently work and live.
Availability and discretion of potential partners are a major hindrance. My choices are ONLY women, or ONLY men -- not both. Back home (San Francisco), the chances of having encounters with bi-men and open-minded women are abundant -- I used to get in more than enough MMF threesomes, or bi-orgies.
In the months before working for my current employer, I was able to experience something I found to be particularly enjoyable: being pegged, or ass-fucked, by a woman. Don't know why, but the act and the thought of it really gets me going!
But, here in the middle or nothing, I've found meeting non-judgmental, like-minded women to be damned near impossible.
The final hinderance, I must also admit, is that I'm picky AF.
I have a long list of "nopes" and "swipe lefts": not too young or too old, (10-years plus or minus is my limit), not going to pay for it, dominatrix, man-shaming and femdom is not my thing, and low-class, ignorance is a definite turn-off.
Yep -- picky AF. So -- I endure.
But just as I was about to commit to 3-years of jerking off to porn (or celibacy) I met Consuela. Actually, I hired her to clean my 2-bedroom condo once a week.
Like me, "Conni" hadn't really intended to come here, as much as she ended up here. Her circumstances involved following a former boyfriend from New York City. He broke up with her a few months after they arrived and moved back East. She found her way to various odd jobs before becoming self-employed as a house cleaner.
Conni is 4-years older than me, born in Puerto Rico, but raised in NYC (full-blood "New Yorican"). She's short, fair-skinned and plump, with big, brown eyes and short, curly hair. She definitely likes to have fun -- she's got lots of personality.
We became instant friends. Three or four months after she started working for me, I asked her to come over for dinner.
"Nothing serious..." I smiled at her, "just dinner." I was lonely and needed the company.
She agreed and came over the next night. We talked, laughed, ate and drank. Eventually, conversation got personal.
"I was startin' to think you was only into guys..." she raised an eyebrow at me after sipping her third glass of wine.
"What gave you that idea...?" I shot back.
"All the pictures of you and 'the boys'..." she laughed gesturing to the photos of several of my male friends (and former lovers). Of the ten photos she was referring to there was only one with me and another woman.
"Oh..." I said realizing her point. "Well...I like both..."
"Aahh..." Conni said, both amused and intrigued. "You like the both the polla AND the coño...?"
"Is that a problem for you...?" I asked cautiously, thinking I might have to hire another cleaning lady.
"Nah..." she said, finishing her wine. "I like both dick and pussy too..."
We laughed and drank some more. I was very attracted to and wanted her to stay the night, but didn't want to press my luck. I called for a car to take her home.
We shared a very promising kiss before she left.
A few days later she came back over for the weekly cleaning. On the surface, it didn't seem as if anything had changed, she cleaned, I went to my home office and worked. When she was done, as she always did, she knocked on my office door, and we talked and hung out for a while.
This time we talked about the dinner, the conversation and the kiss. We mutually enjoyed all of the above. This time she asked me to have dinner and watch TV at her place.
I went over the next night and we ordered take-out and opened a bottle of wine. We found something that neither of us had seen yet on Netflix and started binging the first season.
We were sitting side-by-side on the couch, her head resting against my shoulder. We occasionally leaned towards each other for a quick peck or a nuzzle. We barely made it to the third episode before things really got heated.
"Sorry, papi..." Conni suddenly said, switching off the TV. "But you got me horny as fuck...!"
She straddled me in the now dark living room of her one-bedroom apartment. The way she kissed me almost made me come in my shorts. Conni has the most amazing tongue I've ever experienced.
"But wait...wait, real quick, a'ight..." she suddenly said panting, bringing everything to a halt, "I don't wanna fuck you yet...I mean, I DO, but not yet...not tonight...it's too soon..."
I didn't know what to say, so I didn't.
"I ain't tryin' to be no tease or nuthin..." she continued, pulling off her t-shirt and pulling at mines. "But I need my rocks off, an' I know you prob'ly wanna get yours too..."
I was only barely following what she was trying to say, but if it all meant "get me off and I'll get you off" -sure, fine, okay, I'm down!
"Yeah -- I'm good...!" I agreed. Although she could have probably made me agree to drink poison at that moment.
We fumbled around on her small couch like anxious, horny teenagers for a while, pulling at clothing and belts and buckles and zippers until we were both stripped down to only socks.
We sucked on one another's nipples, she stroked my cock and massaged my balls, and I fingered her warm, wet pussy and felt every inch of her perfectly, rounded ass.
Conni pushed me onto my back, turned and tossed a leg over my head. She lowered that warm, wet pussy onto my face as she swallowed my cock whole. From there it was a contest to see who would make whom blow their load first. We slurped, sucked, moaned and fingered each other for what seemed like hours. It was actually only minutes, but it was amazing!
Conni won the contest. I unintentionally gave her the "clue to victory".
While eating her out, I spread her cheeks and inserted my tongue into her equally welcoming, tight asshole. She repaid the favor, and one-upped me -- inserting two, wet fingers into my ass, while she sucked my balls and masterfully stroked the head of my cock.
"Mmu-phuck...!" I mumbled from between her muscular ass-cheeks.
She snorted a laugh and pushed her fingers deeper, massaging my prostate, and deep-throating me. She found my "special place".
I saw stars. My legs stiffened and tightened and I literally trembled all over. I unloaded into her throat.
"Aye, papi..." she said when I was done. Conni sat up on my face and began grinding in small circles against my chin. "My turn...!"
I applied more pressure to her ass with my tongue. I was able to find her clit with my free hand and match her motion.
Conni's thighs began to shake and she suddenly stood up.
"Aye, fuck...!" she screamed, holding onto the couch for balance. Her leg and ass muscles flexed and clutched.
A few minutes later we were curled up in each other's arms and catching our breath.
"Next time..." she panted, pointing to my dick, "...you betta' fuck me good with that thing..."
As if I had a choice.
We spent the rest of the night laughing and talking and finishing the wine. Conni had lots of questions too. Apparently, I was her first bi-man.
"Do guys suck dick better than girls...if you couldn't see their face, could you tell the difference...? What's the biggest dick you've ever sucked...? Do you like to swallow cum like I do...? Did you take it in the ass...? Do you like it hard and fast, or slow and steady...?"
I answered honestly for each: I prefer women over men for blowjobs, they tend to be less aggressive...the biggest dick I ever had was about 10-inches...yes, I swallowed -- and gagged...I did take that same 10-incher in my ass -- had to call in sick from work for 3-days after, I was sore as hell...sometimes I like it hard, sometimes slow -- depends on the person and the situation...
Then I added my "little secret" about being pegged. She seemed especially interested.
"Really...?" she smiled. "I've strap-on'ed plenty of girls...never did a guy..."
I shrugged as if it meant nothing. But when I got a car home later, that was all I could think about. I jerked off before I went to sleep -- thinking about Conni fucking me in the ass.
Whoa...
We traded naughty texts every day, and even mutually masturbated over a FaceTime call.
We agreed to go out again on the night of my next house cleaning. She arrived that day as she usually did, cleaned my place and then we spent the afternoon hanging out in my office.
She had an overnight bag in her car and used my guest-room to shower and change for our date. We went out for drinks and then dancing.
When we got back to my place, we sat on the couch, drank wine and talked. My balls were sore from a full day of anticipation.
"Is it OK if I stay over...?" she asked, sounding almost shy when she asked.
"Hell yeah..." I grinned. "I was thinkin' about kidnapping your sexy ass..."
I pulled her into a long, wet kiss. This time I did cum a little.
"I'll be right back, papi..." she said breaking the kiss. She disappeared to the guest room for several long minutes.
When she came back, Conni wore only a thigh-length, grey t-shirt. She'd even removed her jewelry and make-up. She looked amazing.
She was carrying a small nylon bag. She reached in an pulled out a black, strap-on dildo, it was probably 8 to 10-inches.
"I'm down if you are, papi..." she smiled.
My asshole twitched and I came a little more.
She helped me undress, then she removed her t-shirt. I ate her out and made her cum -- hard. Then she had me sit down and gave me another amazing blowjob. When she was done, she had me draw my legs up to my chest and spread my ass. She lubed me up with oil from a small tube in the nylon bag. Conni teased me with the tip of the dildo, pushing the head into me and twisting it in circles. Then she pulled it out, and slowly put it back in, only to pull it out again.
I moaned aloud. I wanted her to fuck me with it so badly.
She applied a generous portion of lube to the strap-on, and then to my hungry asshole, teasing it with her fingers. I watched her in anticipation as I continued to hold my knees up.
She took her time, putting it on slowly and stroking it a few times.
"You want this, papi...?" she asked teasing me.
"Yes...please..." I begged. I bit my lower lip.
Conni took aim and slowly entered me. The sensation was so amazing that I almost lost it.
Halle-fuckin-luyah!
She pumped me nice and slow, taking her time, watching my reactions. She was definitely not a newbie when it came to using a strap-on. Conni had the moves down and she stroked me right.
She slowly stroked my cock as she fucked me.
"Tell me how much you like it, papi..." she whispered.
"I fu- I fuckin' love it..." I moaned, barely able to speak.
A few minutes later my cock erupted, spilling jism all over her hand.
"That's it, baby..." she assured me. "I got you, papi...I got you..."
My toes were curling and I was light-headed. She continued stroking and squeezing my cock until it was empty and limp.
Conni held the strap-on inside me. The muscles around my anus twitched.
"I'm not done yet..." she grinned.
She gave me a few more quick thrusts and then slowly pulled out.
"I want you over here..." she said, pointing to my coffee table. "On your knees, papi..."
I followed her instructions, and soon I was on the table on all fours.
"Omifuckingod...!" I whispered. From the look on her face I could only imagine the ass-pounding she was about to give me.
Conni didn't disappoint me.
But first she stood in front of me, and rubbed the tip of the dildo across my lips. I opened my mouth and sucked it in. She placed a hand on my head and slowly pumped my face. I could taste the lube, my own fluids and some of her sweat.
I could already feel myself getting hard again.
She pulled away and walked behind me.
"I'mma take good care of you, papi..." she said giving me a smack on the ass.
I spread my knees wider and gripped the edges of the table.
Conni spread my ass-cheeks and pressed the tip of the dildo against my hole. I closed my eyes tightly and bit my lower lip as she pushed herself in.
"Oh fuck..." I gasped involuntarily when she bottomed-out. I felt her thighs press against mines.
"You ready, papi...?" she asked as she began to slowly pump me. She gripped my hips firmly. I could only moan in response.
Conni banged the fuck out of me for almost 20-minutes -- I loved every second!
My asshole and my knees were sore, I was covered in sweat and my eyes watered. My throat was raw too -- I hadn't realized that I yelped and squealed with each thrust.
"Is it good, papi...?" she'd ask me every few minutes.
"So fuckin' good..." I recall answering at least once. My head was in a daze.
"I need some dick now, papi..." she panted. She was also covered in sweat.
She pulled out of my tingly, sore asshole and helped my up from the table. She removed the strap-on and tossed it on the couch.
I followed Conni to my bedroom. She climbed onto the bed and spread out on her back (if she were a cat, she'd be purring).
"C'mon, papi..." she moaned. "Gerry, I need your dick up in me now...!"
I think I got even harder.
I climbed onto the bed and mounted her. She felt even better than the dildo.
"Fuck me, papi..." Conni moaned.
I really gave it to her. I mean, I REALLY gave it to her. My 2nd Boner is usually indestructible and it definitely didn't let me down this time.
Conni came so many times that she begged me to stop. We were both sore, numb and satisfied by the time we were done.
My ass and balls tingled all the next day. Both of us "complained" about being sore, but we fucked a few times anyway.
Recently Conni mentioned a friend of hers who also happens to be pretty good with a strap-on.
I've been hard ever since she mentioned it...
After our intimate encounter, I couldn't help but think about being pegged again. I found myself seeking out interracial porn featuring bi-male scenarios, particularly ones involving a man being ass-fucked with a strap-on.
In my search for non-judgmental, like-minded women, I discovered a new online community dedicated to bisexual individuals. I joined, hoping to find someone who shares my interests, especially the notion of being pegged by a woman.
