#42) A Strap-on Gift for Cherry, Part II – GRAPHIC CONTENT

We made an impressive pair waltzing into the sex shop, both of us with bed-head and a dazed look in our eyes (like we’d just climaxed and were still groggy from it), smelling of pussy, Cherry with that crisp British accent, her silver collar now prominently on display and the red leash in my hand. She elected not to get down on all fours this time.
Cherry and I were confronted with a mind-boggling array of strap-on harnesses once inside the neon store. We decided we both liked the one named “Full Curves Harness” because it seemed the most secure, and because it let us choose the size of the phallus to match with it. (Of course, that made it the most expensive, not counting what dildo we chose to pair with it.)
There is a meme/video I saw recently. I want to state up-front that this is not my idea, I’m borrowing it. Some women are shopping for a strap-on, and one presciently observes, “I think it’s a Harry Potter situation. Just like the wand chooses the wizard in the book series, the strap-on chooses the recipient.” That’s exactly how we felt, standing in the Hustler Store. We looked over their manhood-resembling merchandise in this category, and waited for the right one to speak to us. At first, Cherry was attracted to a big, thick, veiny one. She picked it up, clearly impressed with its heft.
“Let me caution you about something,” I mentioned, “which ever one you choose will first be used on you vaginally, but then is going up your ass. Choose wisely.” She blanched, put the thick dick down. We agreed on something more sensible, medium-sized. I put both items in her hands. “You are to make this purchase. We’ll use my credit card, but you are to explain to the clerk that this purchase is for use on you, on both your orifices. If I have to speak up to clarify anything, I promise I’ll turn you over the bumper of my car, bare your bumper, and spank you in broad daylight. Are we clear?” She was panting slightly, making those mountainous peaks rise and fall. I put on a pair of sunglasses for anonymity, making Cherry feel all the more vulnerable.
Cherry was blushing hotly before we even got to the counter.
“We’ll take these two,” she volunteered with forced energy.
The clerk, looking bored, nodded, started ringing them up, repeating in a monotone as he’d been instructed to do with each sale, “Did you find everything okay?”
“I think so… I think this dildo will be the right size for both my sex and my… um, backdoor… Do you have any advice?”
Maybe it was that enchanting British accent, maybe her heaving breasts, maybe the fact that Chery is, as I’ve tried to convey all along, drop-dead-gorgeous, but the clerk looked up, blushed as deeply as she did, muttered, “Gee, I dunno…”
“Okay, thank you. I don’t imagine I can return it, once it’s been used…?”
“Ah, no, ma’am.”
“Very well then.”
“So, that’ll be all?”
“Yes.”
He told us the total including tax, I handed him my plastic.
Walking through the parking lot, I reeled Cherry in by her leash. “You did that very well, Cherry!”
“It was mortifying!” she mock-protested.
“Mr. Jones informed me that you love humiliation… If that wasn’t sufficient, I can go ahead and spank you right here…” I reopened my car door.
“That won’t be necessary, Mistress, if it’s all the same to you…”
Once inside the closed car, I kissed her passionately. Cherry pressed back against my mouth, opening hers, getting our tongues involved. My hand worked its way past her clothing to dip-stick-check her fluid levels. I found her pussy very wet. “Methinks the lady doth protest too much. You enjoyed that! When I get you home, you’re in for a good spanking.”
“Yes, Mistress.”
Personally, I enjoy Public Displays of Affection, as well as Public Displays of Discipline…”
“Maybe it’s because I’m British…” she offered off-handedly.
“That you need frequent discipline or that you are easily embarrassed?”
“Both, Mistress,” and that sly smile played on her lips once more.
“Just wait until I get you home,” I mock-chastised.
Cherry pressed her balled-up fists between her tightly-pressed thighs, “I’m not sure I can, Mistress.”
We were pulling into my driveway.
“Get your pants and knickers down to your knees, young lady,” I ordered. Cherry looked back at me horror-stricken. So I put her at ease by adding, “My neighbors have seen it all before, but it’s always been me who was the one who was bared and getting her butt beaten by a Top. It’s nice to have the shoe on the other foot. I mean it, young lady, you’re clothes had better be down before I get around to that side of the car…”
I opened her car door, helped her out, kept a tight grip on her arm as I aimed spank after spank to her undulating backside. It was a long, slow walk to the front door, punctuated with swats.
Again, once behind this closed door, passions were unleashed.
“God, that got my juices flowing!” I enthused, ripping the rest of her clothes off as I kissed her.
“Mine, too!” she countered as she pulled at my clothes and kissed back.
We only got as far as the living room, to that same straight-backed chair we’d christened when Cherry first arrived. I put her across my knee. I loved how soft she was, how right she felt in this position, how magnetic her butt cheeks were. I couldn’t keep my hands from wandering, caressing, exploring. I must have gotten lost in their sojourn.
“Are you going to spank me or what?” her disembodied voice came back at me.
I answered her with a good, hard smack, and didn’t relent for a long time of uninterrupted spanking, until Cherry was yelping, almost sobbing, and trying to dodge the onslaught.
I pushed her off my lap onto the carpet, saying, “I can’t wait another minute! I have to have you! Where is that package?”
Cherry had carried it in, but dropped it half way across the living room floor. I retrieved it, cinched myself in, and practically dove on top of her. She’d chosen to lie on her back with her thighs splayed wide. She was so wet, I slid the phallus into her with one smooth thrust. Suddenly we were eye-to-eye, joined in love-making, rocking in synchronization, breathing in one another’s exhalations, intimately connected, fucking.
“Do I… have to… hold off cumming…?”
I interlaced my fingers of both hands with hers. “No, Sweetness… cum with me… cum as much as you want… all you can…”
She did, I did, we did! It was so cathartic, so affirming, so hot. The French have a phrase, “le petite morte’ which means little death. We each fainted dead away from the draining series of climaxes, then came-to together.
In a soft, solicitous voice, Cherry asked tentatively, “…You said something about anal…?”
Looking her deep in the eye, I asked, “Do you wanna? Do you like it? Have you done it much?”
Cherry smiled and answered, “Yes, I don’t know, and no to each question respectively.” I took her by the hand (wanting more intimacy than the leash afforded) and walked her to my bedroom, and over to the bed.
“Assume whatever position you’re comfortable in,” In the master-bath, I got the tube of lube and a condom.
Cherry was languidly lying on her side, looking so seductive without even trying. Her magnificent big bum was radiantly glowing, she looked back at me over her shoulder. I stopped in my tracks just to memorize everything I was seeing, to cherish it forever.
“Why the condom? You’re not going to ejaculate, are you?”
“I might, I squirt when really turned-on, but that’s not why,” I answered. “It’ll make clean-up easier.”
“You look really sexy with a phallus dangling between your legs,” she smiled.
“Thanks, I feel really hot!” I said honestly. With relish, I pried Cherry’s cheeks apart and began lubricating her rectum. We both found it erotic in the extreme. “I’m gonna take it nice and slow. Just try to relax and breathe and see if you like it…” I snuggled close behind her, spooning her curves while guiding the phallus between her orbs. Pressing the tip against her dimple, I told her the truth, that I found her to be incredibly beautiful and exceedingly feminine and so very sexy and fun to be with “and I’m inside you! That’s the toughest part. You’re doing wonderfully! Do you feel okay?”
“Uh-huh…” she nodded
“Good girl!” I said, using the words I knew I loved to hear. Now, I’m gonna push it in, real slow, just relax. You still okay?”
Cherry nodded. “I feel so dirty! It’s so fun to… give myself permission to… behave this way…”
“I love being the one to share this with you!” I whispered softly but felt deeply.
Cherry reached back and took my hands, which, having guided the cock into her, were now free. With that connection, she opened up her heart. “The only other time I tried this, the guy wasn’t gentle, like you just were, going in, and once in there, he thrust really painfully.”
“I’m not gonna thrust at all. I don’t like that, either! I think the porn industry taught a lot of men the wrong way to do this. I just find it so intimate. It has such a dirty reputation, and it feels so fucking good!” By this time, I was all the way into her. “Now, help me touch you like you like it…” I whispered in her ear as I fingered her sex.
“Oh, God, that’s… intense! That’s…!” And Cherry came, crumpling into a fetal ball. I slowly, gently eased out of her. Cherry began to softly sob.
“That’s okay! I’ve done that, too. It opens something up inside… let it out…” I held her and stroked her and soothed her with hands and words. I was still talking when I realized that Cherry was fast asleep.
I slipped out of bed, slipped the condom off, slipped out of the harness, and cleaned everything up. I felt it was my turn to reciprocate. I made a sumptuous repast for lunch and brought it in to Cherry on a tray.
She awoke with a look of such sublime innocence on her face. Then a shadow seemed to cross her countenance, and she felt a momentary guilt. This storm cloud passed by quickly though. She had no reason to feel bad. We’d played, experimented, shared an intimate act that bonded us. All this was visible on her pretty features, all in the matter of seconds.
She found her voice, “Oh! This is so nice. You shouldn’t have. I’m your slave…”
“Eat!” and as she did, I took control of the conversation. “I didn’t feel confident when you first arrived,” I confessed. “What we’ve shared, the person you’ve revealed to me has given me my confidence back. Would you be comfortable redefining our dynamic, being switches with one another?”
“Does that mean I can climax whenever I feel like it?” she giggled, and I nodded, and we kissed.
“Lay back,” I said in more-of-a-suggestion and less-of-an-order kind of way. “I know from experience how decadently delicious it is to eat good food while being eaten out…”
Cherry moaned softly at the tastes exploded in her mouth, how it made her replete tummy feel. Cherry moaned loudly as she exploded in my mouth, due to my mouth, as her tummy rumbled through orgasm after orgasm. For my part, I loved discovering how to pleasure a woman by doing what you know feels good, trying variations on that theme like a musical score, improvising, riffing. It seems she discovered a mantra, “Oh God!” which she said over and over and over. When she seemed exhausted, I crawled up next to her on the mattress. I could taste mango on her breath, Cherry could taste herself on my lips.
I had to say what was on my mind.
“I’m falling in love with you…” I said, feeling so naked that goosebumps rose and took flight across my epidermis.
“I’m so glad you risked saying that! I’m falling in love with you, too!” She rolled against me, smooth skin pressing together, wet pussies pressing together, soft mouths pressing together, tongues entwined, limbs entwined, two hearts hammering hard and in unison.
“You’re going to go back to England tomorrow,” I said, sadness flooding over me. “Maybe I can come visit you there, maybe you can come back here, but our ‘relationship’ whatever it is, has to change…” Was there nothing to say to this; Cherry responded with one lone tear falling from her lashes and trickling down her apple cheek. “Some lovers,” I continued, “might get matching tattoos or piercings… We’re kinky… I’d like to cane a tattoo into your ass, and bend submissively to you, to have you mark me in the same way, welts I’ll always wear in my heart.”
To someone else, it might have sounded shmaltzy. It apparently struck just the right chord with Cherry.
“Yes, yes! I love surrendering to a caning with the right person! You are my most-right person!”
“Will you promise to mark me just as hard, mark me as yours?”
“Yes,” and Cherry was about to say Mistress, but caught herself and added, “lover.” She bound out of bed like a child on a late Saturday morning with lots of cartoons and sugary cereal to digest. “I saw where you keep your collection of canes, in the umbrella stand, right by the door, do you have a favorite? Want me to fetch one?”
“Fetch two, the two thinnest, whippy ones,” I responded, and Cherry was gone.
When she returned, she wasn’t quite as ebullient. “Listen, I meant it when I said I love being caned… But I’m also a wimp. I don’t like blood…”
“We won’t break the skin, it’s a hard limit for me, too. Agreed?”
“God, we’re on the exact same wave length!” She handed me a cane, then turned on her heel and bent full over. I stared at her perfect split peach, wanting nothing more than to bury my face between her fleshy hillocks and motorboat my way to heaven. The thought occurred to me that Cherry’s round bottom cheeks almost identically matched her full, round breasts, that her eyes’ irises were matched by her titties’ large areole. She was the epitome of feminine sexuality, a butterball of creaminess, a woman at her pinnacle of ripeness. Cherry’s words pulled me out of this reverie.
“Please lover, will you mark me as yours, mark my bottom with your cane?”
I took position, took aim, gave her a moderate stripe, bisecting both big orbs with a perfect perpendicular welt. Her muscles flinched, her flesh contorted. Cherry yelped, grabbed her cheeks, stood up and danced. As she tearfully uttered a “Thank you…” I turned and took position, said the plea, felt the fear, got my stripe, struggled to absorb the sting. Back and forth we alternated. Neither of us had done this except for practice on a pillow. Both of us did a commendable job of placing the stripes in a tight parallel pattern on each other’s butts.
“Before tonight, what was the most severe caning you’ve ever received?” I asked Cherry. By this time, ten vivid welts shown from each of our buttocks.
She giggled through her tears, “Eight stripes,” she confessed. “And you?”
“Ten,“ I answered. “Shall we agree on twelve total?”
Cherry took a loud, deep cleansing breath and nodded. When both of us had administered and received our allotment, we fell into one another’s arms.
“God that hurts so fucking much!” she yelled. The rest of what she sobbed was unintelligible.
“Hurts like nothing else in this world!” I rejoined, immersed in the exquisite agony. To think I suggested this, volunteered for it, wanted it! But it brought me to a special sub space, a place I’d never shared with another submissive, another girlfriend-now-lover.
“Do you have any cold cream?” Cherry whimpered.
“Good idea!” I scampered to get the jar. We made a circuit on the bed, her painting my welts with the soothing balm, and my index finger tracing each of her stripes with the white, cool ointment.
“Oh, that feels so wonderful!” Cherry sighed.
“I know! …This is when I really crave anal. It just really feeds something in my submissive soul… Will you give it to me?”
Wordlessly, Cherry got up, adjusted the harness and strapped-in, put a fresh condom on the phallus (now understanding why), and started lubing it up.
I got on my elbows and knees and pointed my south end toward true north on the mattress.
The KY jelly was cold when Cherry touched a glob of it to my rosebud. I flinched and jumped. We both giggled at my reaction. She massaged it in, then repeated the process, using one finger, then two. If she attempted to work another glob up me, I was gonna involuntarily climax, so I joked, ”Look at you, you’re already a pro at this!” and we both laughed. “…Fuck me, cherished Cherry, fuck my ass…!”
I meant what I’d said to my lover, anal sex just feels so right after I’ve been punished hard, while simultaneously feeling so dirty, so sinfully wrong.
“Fuck, it’s so sexy seeing the phallus disappear into your butt hole, stretch it…” Cherry enthused.
“It feels just as sexy… as you now know… You know what I really love about butt sex? You can’t be anywhere but in the moment… it’s so intense, it demands your full attention…”
Cherry picked up on that comment and built upon it. “It’s amazing to me that it’s just an inch away from one another, sex up the butt and sex in the pussy, but they each feel so different, both sexy, but unique in their own way!”
I felt Cherry’s rounded belly curves press against my parted cheeks. She was in all the way to the hilt, “balls deep” if either of us had any. Just as I had with her, Cherry reached around and fingered my pussy. I knew that I would be climaxing in a matter of minutes.
“Fuck me! Fuck me up my ass, Cherry!”
“But you said you don’t…”
“I know what I said. I’m saying now that I need you to fuck me. I need to remember this butt fucking for the rest of my life!”
Cherry complied, but did so gently, cautiously.
“Fuck me!” I repeated and pushed back into her to set the rhythm. Once Cherry had matched it, I gave another order. “Spank me! Spank me for being mean to you…”
“It’s gonna hurt so much on your welts…”
“I want it, I deserve it, please do it!”
Ever-compliant, Cherry spanked my cheeks alternately as she thrust in and out of my grip. It did hurt, dreadfully, divinely, just as I hoped. Just enough to inspire me to orgasm instead of impeding it. I collapsed on the bed, Cherry collapsed on top of me, still inside me all the way. The butt sex unlocked something deep inside me, something primal, and I began to cry.
Through my wracking sobs, I tried to explain, “Every time I have sex up my butt from now on, I want to remember this time, with you, when it meant the most to me. Every time I go to sit for the next week, I want to have to think about it, be reminded of how abused I am back there, a memento of you…”
Moved by this declaration, Cherry pulled out, cradled me in her arms, rocked me like a baby, her baby. It took a long time for the tears to run-out, until I was sniffling and hiccupping and content.
“What time does your plane take-off tomorrow morning?” I asked when I could again process thought.
“Ten.”
“I’ll drive you to the airport, we ought to leave here by…”
“I’d prefer to take a Lyft. It’ll be easier, a cleaner break…” and her voice broke at this last phrase.
Already feeling lonely and bereft while still in each other’s company, we fell asleep like mother and child, with me in hollow beneath her womanly tits and atop her porpoise thighs.
We each only nibbled at the breakfast I’d made. Cherry packed and got dressed, while I puttered, doing little things like cleaning the strap-on and its magical manhood. I put it back in the brown paper bag it came in.
“I want you to take this with you,” I said, handing it to her. “Use it, use it often, use it in a photo-shoot with Mr. Jones.”
Cherry accepted the bag, started to say something, but didn’t. “I better pack that in the valise. It’d be embarrassing to have it X-rayed in my purse!” We laughed, but wanly.
She looked exactly like she did when she arrived, wearing that smart cloak, buttoned-up to her neck. I pulled it open to make sure she had clothes on underneath. We smiled again. The Lyft blew its horn. I kissed her. Cherry departed my life just as she’d walked into it, briskly, heels clattering on my driveway.

3 responses to “#42) A Strap-on Gift for Cherry, Part II – GRAPHIC CONTENT”

  1. I cannot recommend the site, spanking-emporium.co.uk/ highly enough! The stories, the photography, wonderful Mr. Jones, the lovely ladies, all are worth checking-out regularly!

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