#166) Breaking New Ground, Exploring New Horizons – GRAPHIC CONTENT

Several days ago, while flying home from a little vacation (the first since Covid-19 took hold over a year ago), my boyfriend of the past three years broke up with me.
What he actually said was that he wanted to open our relationship up to see other people. I was actually thinking that he might propose marriage on our little get-away, so this was quite a shock.
When we got back to his luxurious condo, I began gathering all my stuff to move back to my humble apartment. I let my icy silence answer his overture. I silently wondered if his suggestion was just a way to break-up, so that he could date younger women. I was feeling all of my thirty-two years at this point.
That night I couldn’t sleep. I tossed off the bed-sheet and masturbated. The images that kept invading my mind were of him, so I got up, got my hairbrush, and really paddled the hell out of my ass. Then I was able to rub one out satisfactorily. The orgasm whetted my appetite for more discipline, so I took up the hairbrush again. I’d always found it difficult to self-spank, but my hurt and anger fueled my efforts, and I did a very good job of it. Then I jilled-off once more. I kept this up from 3:30 until dawn.
That day was rainy, so I just puttered around my apartment, eating chocolate and feeling sorry for myself. That evening, as I got ready for bed, I noticed in the bathroom mirror that my butt was bruised from my solo efforts from the night before. So I drew a bath, and used my hairbrush on my tush all over again. On a wet butt it hurt all the more gloriously. I masturbated with the hairbrush handle between sets of swats. The last round, I soaped up both the handle and my butthole, and fucked myself there. I still slept fitfully.
The next day, determined to end the pity-party, I cleaned-up and ran some errands around town, even went to a nice restaurant for lunch (where I read a book while I ate). On my way home, I stopped off at Kroger to resupply groceries. I bought a box of white wine. This was significant because I had not had a drink of alcohol since the previous March, when the virus lock-down began. I’m not an alcoholic, but I just thought I’d do better without it. But I wanted a drink now. I gave myself credit that I bought cheap wine instead of what I really thirsted for, a stiff Blanton’s bourbon.
This was a mistake, however. Alcohol lowers my inhibitions. So I started munching on snacks to accompany the wine. Then I got an inebriated idea. I’ll just phone Kyle, my boyfriend, to express how well I’m doing without him and see if he misses me. He picked-up on the third ring.
“Hi!” I said cheerfully.
“Hi,” he returned, trying to mask the surprise that I was again speaking to him. “How ya doing?”
I took a gulp of Pinot. “Fine… great, actually! I’m sitting on a very bruised butt!”
“Really…?” Kyle replied, and I could visualize his adorable smirk as he said it.
“But, I miss your cock.” It just came out unfiltered.
“Not the rest of me, just my cock?”
“Nope, just your cock. The rest of you is a poopie-head!” I returned, trying to reclaim some dignity. “What’re ya doing”
“Getting to know a new friend, Emily..” he responded.
This made me gasp audibly. I should have followed it with three or four more deep breaths, but instead took another gulp of wine. “Well… I’ll let you get back to that…”
“Jeanie,” he said in that way that melts me, “my offer still stands. Do you want to come over and get to know her, too?”
We all know that I should have demurred and hung-up. Instead, I pondered. The wine was a truth-serum; I did miss fucking Kyle. No one has ever made love with me like him.
“Is she double-vaccinated?”
“Is she clean, or some skank?”
“She’s very nice.”
“How old is she?” I asked with too much vehemence.
I heard Kyle ask, then answered, “She says she’s twenty-four.”
I tried to mask the hurt as I continued, “She’s submissive?”
“Oh, yes, of course.”
“If we… frolic, you’ll wear a condom, a fresh condom for each of us…?”
“Okay,” he returned evenly.
So I returned, “I’m not saying ‘yes’ but I am intrigued. I’ll be right over…”
“See you then,” and he hung-up.
I put on my raciest lingerie, sorry that the matching Agent Provocateur bra, garter belt and panties were a gift from Kyle. I looked for the slinkiest dress in my closet, and was bothered that the little black number was also a gift from Kyle. As were the high, Jimmy Choo stilettos. Maybe he won’t remember, I thought to myself, consoled by the fact that I looked hot.
I reminded myself that I’d been drinking when I got in my car, determined to be extra careful. Then I raced across town to my old haunt.
Damned Emily answered Kyle’s front door when I knocked. She was wearing his terrycloth bathrobe and looked fabulous. She was everything I’m not. She’s tall when I’m of average height. She’s blond where I’m olive-skinned and brunette. She has a big bust, whereas I’m self-conscious about what Kyle called ‘my little cupcakes.’ I hated her before she smiled and said a word. Nonetheless, I was gracious, smiling, taking her proffered hand.
I turned my head when Kyle embraced me, letting him kiss my cheek instead of my mouth. I wondered if he could feel my racing heart.
“You look lovely,” he smiled. He was dressed in his satin robe. It went without saying that he looked good enough to eat to my hungry eyes.
“Thank you. So is Emily,” I replied, trying to be unemotional. They both smiled. “Have you spanked her yet?”
“We’ve just been getting to know one another, discussing backgrounds and preferences,” Kyle answered.
“Have you played in a threesome before, Emily?” I asked.
“Yes,” she answered with that dazzling smile, then added, “too many to count.”
I tried not to look surprised. “I never have,” I offered. “Have you, Kyle?” I said, realizing that I didn’t know.
“Long ago, just once.”
I tried to digest this without betraying my surprise, wondering if that “long ago” was longer than the three years I’d been with him. “I’ve also never been with another woman,” I volunteered, but added, so that she wouldn’t have the upper hand. “I’d like to dominate you, Emily. I’d like to start off by spanking you… very hard. Does that sound interesting?”
“Yes, it does, Jeanie,” Emily responded letting the robe fall open. She was wearing the tiniest thong bikini underneath that I’ve ever seen. The top two triangles of fabric were barely big enough to cover the aureolas of her nipples, the bottom triangle did not cloth her trimmed pubic hair, just stretched across her camel-toe pussy. I imagined the commotion that her attire must have caused at Kyle’s condo’s pool. She interrupted my thinking by adding, “or should I address you as Mistress?”
“That would be nice, Emily, good girl. Take that robe off,” I directed, as I pulled my dress over my head and threw it on the couch. Kyle joined us in being ready to play by shrugging out of his robe. His bathing trunks were tented out by his erection. I noticed that Emily’s clothes were piled on an armchair, right next to a satchel. “Did you bring some toys with you to play with?”
“Yes, I did, Mistress,” she answered with eyes lowered. I confess that I was loving this. I opened the overnight bag. Among other things, its contents contained a strap-on harness and phallus.
“Oooh! This is fun!” I exclaimed as I pulled it out. “I think I’d like to fuck you, after that spanking I mentioned…”
“Yes, Mistress,” Emily demurred.
“Maybe up the ass…”
“Yes, Mistress.”
I turned to Kyle, “While you fuck me,” I said, and he smirked. “…Maybe up the ass…” and he smiled more broadly.
I took Emily by the hand. I carried the strap-on in my other hand. Emily carried her satchel of other toys in her other hand, and we strolled up the steps leading to Kyle’s boudoir. Kyle walked behind us. Halfway up the curved staircase, Kyle noticed my buttocks through the lacy lingerie.
“Your bottom is marked!” he remarked.
“Yeah, I got a really good spanking the other evening,” I said over my shoulder, hoping that he wouldn’t inquire any further because we both knew I wasn’t a good liar.
I threw the strap-on on the big bed, turned to Emily and pushed both hands under that skimpy bikini top to seize her nipples, as I kissed her open mouth passionately. Her tits were fake and felt strange, too firm, not soft. But in my mouth, her nipples hardened deliciously. Hers were the first nipples I had in my mouth since my moms, but I hadn’t forgotten what to do in all the intervening years. I sucked hard until Emily threw her head back and sighed.
“My nipples are very sensitive…” she whispered, “you can bite them if you want to drive me mad…”
I did, my hands moving down her lush body. One hand worked underneath her bikini to finger her pussy, while the other delved up the crack of her bubble butt. Emily cried out with pleasure.
“Somebody needs a spanking,” I intoned, trying to sound domineering. I sat on the bed and pulled Emily over my lap. That’s when I caught sight of Kyle standing just inside the doorway. He had his bathing-suit off and was stroking his erect cock. My hand circled her round rump.
“I promised you a good, hard spanking. Are you ready?” I intimated.
She nodded.
I unloaded on her. I’d never spanked anyone before. I had fantasized about what I was doing for the first time. I found Emily very erotically arousing. At the same time, I resented her, was jealous of her, hated her for being young and firm and beautiful. I took it all out on her ass. I spanked her hard right from the start and didn’t slow up for a long time. Emily’s fair complected cheeks warmed and reddened wonderfully. Before I stopped to catch my breath, they were sizzling hot and deep magenta.
There’s a leather paddle in that chest over there, Emily. Get up and bring it back to me,” I ordered. “Your big butt is hurting my hand,” I added as I watched her wriggle her way across the room to do as instructed.
Emily offered the implement to me.
“Is this the one you want, Ma’am?”
I nodded. “Are you ready for your second set?”
Emily answered by crawling back over my knee and arching her abused arse up at me invitingly. My heart wasn’t softened by her cute little squeals and mews as I paddled her all the harder. Out of the corner of my eye, I spied that Kyle was not softened either, he was rock hard and rampant.
When I’d worn her big bum out with the paddle, I gave her several smacks on the backs of her thighs for good measure, then rolled her off my lap onto the carpet. It pleased me to see how furtively she rubbed her backside, how tear-streaked her other cheeks were. I peeled my underpants down.
“Look what you’ve done to me…” I said to Emily as I parted my labial lips, so she could see the arousal besmearing my pudendum and thighs. Get over here and lick me clean!” I commanded. Emily obeyed instantly. She proved to be very expert at eating pussy. I climaxed loudly.
The true Dominant in the room was feeling neglected.
“Let’s form a daisy-chain. Emily, get on your elbows and knees on the bed. Jeanie, put on the strap-on and get behind her. Fuck her pussy while I fuck yours.”
We scrambled to obey.
It made me feel empowered to cinch-up the harness and have a phallus wave around in front of me. It was sensory overload to rub Emily’s blazing buttocks, part her wide, guide my pseudo-cock into her wet and engorged vagina. It nearly blew my mind to feel my favorite cock in the whole world push its way into my ready and eager va-ja-ja. Emily ejaculated an ear-splitting cry and ejaculated into orgasm.
Kyle leaned in and growled in my ear, “I was beginning to think that you were over me…”
I didn’t want to confess that I didn’t know if I’d ever get over him, but told the truth when I responded, “I just want to be underneath you… fuck me… hard!”
He did. I came, trying hard not to collapse on top of Emily.
“Are we ready for some butt sex, ladies?”
He pulled out and produced a tube of lubricant. I confess that I really enjoyed anointing Emily’s rosebud. Maybe this was influenced by the ecstasy I was experiencing with Kyle’s fingers simultaneously up my tooter.
In an evening of firsts, butt fucking a receptive submissive completely blew me away. Taking it up the ass from my (previously my) cocks-man at the very same time was the ultimate. I felt like I was breaking new ground, territory I fervently wanted to explore further. Exploring bi-sexuality opened up whole new horizons, twice the population of people to romance and fool around with became visible in my mind’s eye. I felt like I’d been tossed around by a tempest, nearly drowned in the tumult. As I gazed at Emily’s pretty posterior as I impaled her, I thought of my kindred sister, Miranda in Shakespeare’s “The Tempest.” I quoted her as I fucked, “O brave new world that has such people in it!”

7 responses to “#166) Breaking New Ground, Exploring New Horizons – GRAPHIC CONTENT”

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