We left Jenny and Brad with a decision to make and Jenny in a state of heightened concern:
“Well, Hon, I was hoping, just wondering if it would be OK if Steve-O calls me? And, if he calls, could I hook up with him? Oh please, I will so make it worth your while when I return home.” Again, silence.
Oh, shit.
Brad got up from the sofa and walked into the kitchen. Did I overstep my bounds? Did I hurt my dear Brad? He returned in a few minutes with a beer and a glass of wine, and I started breathing again.
He sat down in his lounge chair instead of the sofa next to me. He looked me in the eye and said, “I’ve always selected your dates and even directed them on occasion. Now you want to run off and run this Steve-O character whom I’ve not even met. Before I would even consider such a departure, I’d need to run a background check on him and perhaps speak to him on the phone.”
He told me he’d run some background checks and get back to me. I went to bed worried that night.
The following day, I decided to check in with Sheri and see how her training was going, but I thought I’d check with Russell first. They provided me with a glowing report, so I thought I’d open a SKYPE call with Sheri.
A few days later, Brad came home from work and said, “Honey, we need to talk.” Oh shit, now I was shaking. Did I cross that line and piss off my Lord and Master, the man I love?
“Well, Jen, I’ve run several different background checks on this Steve-O and even checked with a half a dozen of his clients. He came back with excellent references. I’ll need to speak with him on the phone, of course, but I’m inclined to let you have your fun with him. I just need to ask, is there any emotional attachment going on here that might shake the foundation of our marriage?”
“Oh, God, no! Brad, I just really like his magic hands and nice rock-hard cock. You’re the only man for me, darling, my true and forever love.”
As odd as it may sound, I knew this would be fine with Brad. I ran up to him and jumped into his arms. Sometimes being 5’2” with a 6’3” husband comes in real handy.
That night I ravished my man, and for the first in years, I wore him out. We both went to sleep contented with enormous smiles on our faces that night.
~~ Sheri ~~
Russell and Jenny agreed that I was an ideal sub because I was a natural people pleaser; well, their term was a kiss – ass. But because of that, I ended up with very little punishment. I even did so well that the computer chimed with a Skype call unexpectedly on one Wednesday night, and it was Jenny with a surprise.
“My pet, you have done so well in training so far. I have a special gift for you this evening. I want you to move me into the living room so I can be there. Make room for a massage table, then take your clothes off, and your surprise will be coming through the door in five minutes.”
At exactly 7:00 p.m., Russell and Steve-O walked through my front door, Steve-O carrying his massage table and his box of accouterments. And Russell carrying a large wicker basket covered in netting and tied with a pink bow.
“Hello, boys,” Jenny greeted from the computer. “I am excited to give my little pet this special gift tonight. Elizabeth put a lot of work into putting the basket together because she felt like our whore here showed enough control to be able to use these items with me over Skype to enhance our relationship. So, Russell, you go first, and then Steve-O, you can finish us up. And I will be here watching the whole time!”
Russell sat the basket on the massage table, now set up in the living room, and told me to open it. I felt a little giddy, like a kid on Christmas morning. When I pulled the netting back, the large basket was full of bottles, tubes, boxes, and bags. I didn’t even know where to start! So, Russell grabbed a bag and said, “let’s start here.” I opened the drawstring and took out several pairs of silk panties in gorgeous jewel-tone colors. “These are crotchless panties for when you are playing online or in person. You will have easy access.” The next bag held three pairs of silk stockings with garter belts. The other bags contained various lingerie: thongs, nighties, teddies, bustier, bra/pantie sets, blindfolds, and one amazing black floral silk robe. “Elizabeth will be over in a bit to throw away every boring bra, pair of granny panties, and set of PJs with an animal or a phrase on them.”
Boxes came next! There was a vibrating butt plug that was bejeweled and a very life-like dildo with a suction cup on the end. I looked at Russell quizzically. He rolled his eyes and said, “don’t worry, I’ll explain it later.”
There was also a wand very similar to the one at Russell’s house, a vibrating dildo, and a glass dildo. I didn’t even have to look at Russell this time. “I’ll explain this later too.”
The bottles and tubes were last. There was water-based lubricant, silicone-based lubricant, anal jelly, and Tickle Me Pick clit stimulant gel. There was also G-spot stimulating serum, peppermint arousal balm, and edible massage oil (butter rum flavor). Russell explained this was to be taken to the spa for appointments with Steve-O. Eighth, anti-bacterial toy cleaning spray.
“Oh, there is one more box that didn’t get in the basket. This will also come with you to the spa for me to use. We can alternate the edible and this.” Steve-O handed me another box, and I opened it to find a Hemp Seed Sex-sensual Massage Candle. Steve-O explained that wax turned into oil for the massage as the candle burned.
My mind was overwhelmed. I don’t think they sell all of this at Bath and Body! I had no idea there was all this stuff out there for sex. And I had a feeling this was just the tip of the iceberg.
“Little slut, we will get to use all of these during our three months apart, so just find a safe place for them, and Do Not use them without my permission,” Jenny instructed. “Steve-O, you are up.”
Steve-O pointed to the massage table, and I eagerly jumped up without hesitation! This part I knew!
“Russell, why don’t you hand me that edible oil. You can take any of the other things you want to add, and we will get started.” Oh, I thought, this is new; Russell is going to be in on the massage.
Steve-O positioned the computer so Jenny could see well, then he poured a good amount of oil on my back. He started with those familiar long, deep strokes that were so relaxing, taking all my stress away. He worked my neck and the muscles down my spine. I felt his knuckles kneading the tightness out of my low back as I realized that the oil did smell like buttered rum. Just as that dawned on me, another realization hit, that as Steve-O was moving to my glut muscles, a tongue was licking slowly up my back, stopping for gentle kisses, then licking again. Goosebumps rippled through my body. Strong hands stroke my butt muscles pushing from in to out, stretching my cheeks apart, pulling the tension away from my body. And, in contrast, the softest of kisses continued down my back. Steve-O moved down to the back of my thighs, pulling and stroking hard on those hamstrings. I feel Russell’s tongue licking my ass cheeks softly, and I can’t help but tense up.
“No, no, no little pet, you must relax!” I had forgotten that Jenny was even watching from the computer. I consciously make myself relax as Russell moves his tongue across my low back to the other cheek. Steve-O focuses both hands on one leg, moving up and down a little higher with each stroke until his fingers graze my outer lips. Just then, the tongue gently and unobtrusively licks right down the middle of my ass, setting off every nerve in my body. A deep moan comes from somewhere in the depths of me that I have never accessed as the men continue to rub my velvety lips and lick down my bum crease.
Hands still touching me so as not to lose contact, Steve-O taps me to roll over, and I obey. Spread eagle and buck naked on his table, I look over at the computer and see that Brad is massaging Jenny as well. And she is moaning in delight. Russell takes the tin of balm and rubs some on my nipples. Immediately there is a hot, tingling sensation that makes my mouth water, and then it turns cool, and he blows gently to make the cool sensation even greater. “Oh my god,” I moan as my head rolls back, and I pull my hair. Next, he applies the clit stimulant gel and then the G-spot stimulant gel. Slowly I feel both getting warmer as the blood flows to make them swell with sensitivity and excitement. He looks at Steve-O and says, “She’s ready.”
Steve-O pours oils on my tummy and starts to massage my upper body. He swipes his hands around the sides of my breasts, massaging my shoulders, down my arms, and my hands. With long expert strokes, he comes back up to my neck and releases all my tension. He moves over my collar bones, making small circles, down between my breasts with one hand over the other, then large circles around my tits. Over and over, my nipples so hard with that cooling arousal sensation that they feel like they might pop right off my chest. He finally starts to rub and squeeze my tits, circling my nipples, pinching them, squeezing them. “Oh, Yes,” I yell. I have never cum just from having my nipples played with, but I knew it was possible, and now I knew why!
Next to me, I heard a male voice moaning on the computer, and I look to find that Mistress Jenny is giving her husband a blow job while I am getting my tits rubbing to the point of near climax. Steve-O notices too. He keeps circling, pinching, rubbing; I keep screaming; until we finally hear Brad grunt out his relief. All the while, my clit, and g-spot are throbbing, so engorged I think they might burst.
Steve-O slides his powerful hands down my tummy, continuing his circular motion, working my upper thighs in those long, deep strokes, down to my calves, and then back up to my thighs. His hands move deftly in smooth, confident strokes in between my thighs and my folds. I push my hips up slightly to meet him. He starts massaging my outer lips, and I know my sex liquid is dripping out now, my hips are writhing, and I need to cum. Russell leans over and pulls the outer lips apart so Steve-O can gently rub inside. “Oh, Fuck!!!”
I can’t help myself. Steve-O keeps rubbing while Russell starts rubbing my clit in slow up and down strokes. Oh, shit, I am overwhelmed with sensation, my nipples are still tingling, and these boys are rocking my pussy, especially with the hot sensation from the stimulant gels. Just when I think I can’t take anymore, Steve-O slides one, two, three fingers into me and lands on my g-spot with no trouble at all. Once he starts rubbing, I am done. “I’m gonna cummmm!!!”
The voice from the computer says, “No slut, we are going to cum together. Get ready. I am almost there.”
I glance over to see that Brad is ramming his cock into Mistress Jenny from behind and has his finger in her ass. “Okay slut, Cum Now!” We climaxed at the same time, squirting loads and loads of cum all over our respective gentleman.
My surprise night was two weeks before I headed to Florida to see Mistress Jenny. And after that, I was even more determined to be a good sub. Whatever humiliation or task was worth it for what she gave me. So, I worked hard during the rest of the training not to make mistakes.
~~ Steve-O ~~
After getting a passing grade for her training, as recited by Sheri above, I flew to my brother’s vacation home in Marathon in the Florida Keys. From the plane, I placed a call to Jenny in Key Largo.
I was getting hard thinking of that smoking Hot Wife, Jenny, when she answered. “Hello, Jenny?”
“Yes, who is this?”
“It’s Steve-O from Kentucky. The masseur. Do you remember me?”
“How could I forget? You’re hot as hell! I only wish my fucking husband hadn’t forbidden me from cumming; that mean SOB!”
She had a good laugh before reminding me that she loved, honored, and obeyed her husband. “Honestly, I’m just so lucky that he likes to share me.”
“Yeah,” I said. “I remember that, and I don’t mind telling ya, I found that rather strange. How did you talk him into that?”
“Oh no, you got it wrong. He talked me into it! I don’t understand his odd little fetish, but I have the best sex life you can imagine. So, what can I do for you, gorgeous?”
I shook my head and smiled at that news. “Well, sexy, your sex life is precisely what I’m interested in. If I remember correctly, we both enjoyed the massage I gave you. Too bad I couldn’t finish it off with a happy ending.”
“Oh my, Steve-O, you have no idea how badly I wanted that. I was in heat! My husband had forbidden me from coming until I got to Russell’s, and I exploded when he shoved his massive cock in me. If I remember correctly, though, you are equally gifted.”
“Well, Hot Cheeks, I’m calling from the plane and will be landing in Key West in forty minutes. I’ll be staying at my brother’s place in Marathon and will have the place to myself. I’d just love to pick up where we left off if you’re available.”
“Geez, Steve-O, I’m going to have to change my thong after this conversation. They are drenched, and you’ve made me horny as hell. I’ll need to speak to my husband first and get his permission, though. Oh, be warned, he may want to speak with you first. No facetime, just a phone call.”
It seemed kind of strange, but time with Jenny would make it worth it.
After I landed, I saw a call coming through from a number I didn’t recognize. Normally I would let a call like that go to voicemail, but I hoped it was a call from Jenny’s husband.
“Hello, is this Steve-O? This is Brad, Jenny’s husband. I just wanted to touch base with you for a number of reasons.”
“Yes, this is Steve-O. Jenny said you’d be calling. What’s up?”
“Well, first of all, I wanted to let you know that, as long as she is not harmed, you have my permission to use Jenny however you want. I realize not every guy understands my way of thinking. But I enjoy knowing when other men play with my wife. She’s a submissive little slut who enjoys impact play, and she will, no doubt, take all you can give her and more,” Brad explained.
“That’s awesome to hear because I want to tan her sexy ass and whip her pussy. I want to hear her begging for more while turning her creamy cheeks bright red and make her pussy sting,” I replied.
“Jenny loves rough sex, so the harder you pound that sweet honey hole, the better. She likes her ass fucked too. Plus, my wife sucks cock like no woman I’ve ever known.”
Just thinking about having Jenny naked and all mine to use was a fucking turn-on!
“Is there anything I can’t do?”
“She’ll use her safe word if there is anything she isn’t comfortable with. My only rule is no permanent holes or marks. Don’t get me wrong. I expect to get her back with marks from your flogging, but the kind that fade over time.”
“Yeah, that’s totally cool. I didn’t come prepared to play like that, though.”
“No worries, I will send Jenny with her paddle, flogger, and whip. She likes her tits whipped with the flogger if you’re into that.”
“Holy shit, she’s a freaky little slut, isn’t she? And it doesn’t bother you that I’m gonna spank her and fuck her blind?” I asked.
“Not at all,” Brad said. “Jenny is my wife, and she loves me. Nothing will ever change that. It turns me on to think of other men desiring her and even having her, knowing all the while that she belongs to me. So, although she’s yours to use while you have her, she’ll be coming home to me to share the experience while I fuck her.”
“That’s really hot, man. I don’t think I could allow my wife to fuck other guys. But I’m grateful that you’re into it. She’s so fucking hot. I can’t wait to make her ass and pussy sting and then use all of her holes,” I said.
I kept waiting for Brad to have some weird rule or restriction, but there didn’t seem to be any hard limits. I was glad I was sitting down after retrieving my luggage because I had a raging hard-on by this point.
“So, just to be clear, it’s fine if I fuck her hard? Rough sex is cool?” I asked one more time.
“Jenny loves to be totally dominated. Make her your little fuck toy and go to town, bro. She’ll be ready for you when you pick her up. She’ll be wearing something slutty for you. I’ll even attach her nipple clamps so that her pussy will be wet and ready. If you want, I can send her with a butt plug in her tight little ass to help stretch it a little. Otherwise, you might not be able to penetrate it.”
“That’d be great. Thanks so much, Brad. I assure you that she’ll come back to you exhausted but unharmed. Thanks for trusting me to show your girl a good time.”
“I’m counting on it, Steve-O.”
That afternoon, I opened the door of my brother’s place to find a very scantily clad Jenny with a duffle bag in her hand.
“You’re even hotter than I remember,” Jenny said, her panties already damp with desire. She handed him the bag that Brad had sent along with various spanking implements and a few other goodies.
“Mmm, so are you!” I replied as my cock began to swell. “But even with that slutty outfit, you have way too many clothes on. You need to get naked for me and stay that way until I’m done using you.”
Jenny’s juices were flowing at the thought of being used by this hunky man with the gorgeous Australian accent. She stripped seductively for me and said, “I’m all yours, Steve-O. Brad said to let you do whatever you want.”
“Fuck, that’s hot! The only problem is there is so much I want to do with you. I will just have to fit in as much as possible. I hope you are prepared to be sore and exhausted.”
“Yes, Sir!”
Jenny’s nipples were hard and begged to be clamped. So, I took the Eagle Talon Tit Clamps that Brad had sent with Jenny and attached those bad boys, causing her to cry out.
“Too much?” I asked, a little concerned. I wanted her sore, but I also wanted her to enjoy being used.
“No, Sir,” Jenny said, falling into her familiar role as a submissive slut. “Just the perfect mix of pleasure and pain.”
“Excellent! Now, bend over that couch and present your ass to me, slut. I’m gonna paddle your creamy cheeks until they are bright pink.”
Spank! Spank! Spank! Spank!
I felt my cock throb as Jenny’s pussy started to drip.
Spank! Spank! Spank! Spank!
Jenny moaned with desire each time the paddle struck her, causing a full-fledged, raging hard-on for me. I reached under her and yanked tersely on the chain connected to the nipple clamps.
“Oh, fuckkkk!” Jenny screamed.
I picked her up and set her on the kitchen counter.
“Spread your legs, slut. Brad said that you like the flogger on your tender little pussy. I can’t wait to make your mound as red as your ass.”
“Oh, fuck, yes!”
Jenny’s body flinched with every stroke of the leather as it bit into her delicate flesh. I felt like my cock might burst, but I couldn’t stop yet. It was too fascinating to watch the mix of pleasure and pain on her face while I turned her pussy crimson. Her labia and clit were red and puffy from the flogger, and she was writhing around like a bitch in heat on my brother’s kitchen counter.
I continued tormenting her tender cunt until Jenny arched her back and came violently, spraying her juices everywhere.
“That’s fucking erotic! You came so fucking hard just by having your pussy whipped. You’re one decadent little slut! I’m gonna open you up now with my big cock. First in your pussy, then in your ass!”
I unzipped his pants and let his very impressive dick spring out. Then I grabbed Jenny’s legs and plunged into her dripping hole with one firm thrust.
“Oh, God, you’re so big!” Jenny cried out.
“Just wait till you feel it in your ass, baby!”
I drove my stiff shaft into her soft, wet walls again and again until Jenny screamed as her pleasure came in waves. I pulled out of her and helped her off the counter.
“Get on your knees and suck my cock.”
Jenny didn’t hesitate to lower herself to the floor and open her mouth. She took my massive prick into her mouth and sucked it like a fucking call girl.
I grabbed her head and pushed myself into her throat, causing her to choke a little.
“That’s right, slut. Gag on my cock!”
I eased back to let Jenny take a breath before plunging into her throat again and again.
The hot little slut had me close, but I wanted to cum in her ass. So, I pulled out, leaned her back over the couch where I’d spanked her, and grabbed some lube to get her tight little hole ready for my girth. I shoved two fingers into her puckered star until it relaxed under my touch.
“Get ready to scream again; I’m gonna fuck your ass hard and deep!”
I’d promised Brad that Jenny would be used roughly and come back to him sore, and I intended to keep my word. Grabbing her hips, I drove himself into her back door like a male dog fucking his bitch.
Jenny was screaming and crying. “Oh, God, yes! Fuck my ass hard with your big fuckin’ cock!”
Tears streamed down her face as she received the roughest anal fucking of her life.
“That’s. A. Good. Girl!” I panted as I jackhammered Jenny’s tight anus, fucking her ass harder than I’d ever done to any woman before. Something about her brought out the animal in me.
Just when I worried that I had taken things too far, Jenny screamed, “Fuck! I’m cumming again!”
It was more than I could handle, and I finally gave in. My balls tightened as if being squeezed by a vise grip and then let go as I exploded in Jenny’s ass, coating her bowels with my thick seed.
“Christ, you’re so fucking hot, Jenny!”
“God, I’ve never had my ass pounded like that!”
“I’m glad you enjoyed it, slut. Because I have you to myself for a couple more hours. I think it’s time to make your tits as red as your ass and pussy with this crop. Sit on the coffee table and roll onto your back. Let your arms dangle to the side.”
Jenny obeyed without question. I grabbed the ropes from the back and tied Jenny’s ankles and wrists to the legs of the coffee table, and grinned.
“You look so fucking hot and helpless! You’re making my meat hard again.”
I tapped her tits softly with the crop before delivering several stinging slaps.
“Oh, fuck!”
Jenny cried and moaned. Then she begged for more. I continued his torment of Jenny’s luscious breasts, occasionally swatting her mound and labia as well. I took the whip out of the bag next and painted her body with red stripes as she came again in waves. I switched back to the crop and moved around to the head of the table. I ditched my pants and straddled her head, dangling my balls over her mouth.
“Suck my balls while I spank that slutty cunt of yours. I own you, my sweet little bitch in heat!”
I continued to make her swollen labia sting with pleasure and pain as she sucked both of my nuts at the same time. I felt his climax growing closer, so I turned around, so I was off to Jenny’s right side and stroked my cock, now pointed directly at her face.
“I’m going to cover you with my seed, you dirty little slut!” I growled as I jacked my prick hard. Then, with a guttural, primal cry, I let loose, covering Jenny’s face and tits with rope after rope of my spunk.
I wiped my dick on her tummy and grabbed my phone.
“What are you doing?” Jenny asked.
“I’m taking pictures for your husband. I want him to see his slutty Hotwife covered in cum and marked with signs of a brutal whipping. He’s gonna cream his jeans when he sees you like this.”
I untied Jenny and used the remaining time with her to make her ass a little redder and fuck it one more time. This time while I used her ass, though, I had a huge dildo stuffed in her cunt. As I drove into her, I yanked on the chain, causing the clamps to bite into her nipples.
When I came one more time, I pulled out and covered her ass and back with my seed. I took more pictures for Brad and myself, of course. I envisioned using these pics during those rare times that I couldn’t find a willing partner and had to rely on my hand for release.
“Look at you, Jenny! You’re just a dirty, used slut covered in cum. I hope you enjoyed that half as much as I did.”
Jenny purred, “Thank You, Sir.”
~~ Jenny ~~
I had another wonderful day with Steve-O, and it was just good hard fucking. I had love bites all over my tits, strap marks on my ass, and purple bite marks all around my pussy. I was a well-used and delighted woman.
Then I had a brilliant idea, “Hey Steve-O, Sheri will be at my house the day after tomorrow, and I promised her a graduation party. She did well with her training, didn’t she? Would you care to come over and help rock her world?”
Steve-O smiled and said, “You gonna be there? I’d love to play with both of you.”
“Oh, no, dude! Brad permitted me to play with you here at your brother’s place, but that most definitely does not include fooling around in my home. That’s off-limits. This will be all about Sheri and her sexual graduation present.”
When I got home, I found a note from Brad saying he’d be out of town the next three days. Damn, I needed him now! In any case, Sheri would be here tomorrow, so I started to get everything ready.
I had Steve-O ready for tomorrow and thinking I needed some more help with Sheri’s surprise. I called Russell, and he said he’d bring two more young guys and a couple of fun ladies as well. Oh, this was starting to sound like fun.
~~ Sheri ~~
Finally, the day arrived! I was flying to Key Largo to visit Mistress Jenny. I was confident that I’d done well in my training and couldn’t wait until I could see her. She had promised me a surprise, and I was getting wet just thinking about it.
I received a text from Jenny just prior to boarding the plane. It said, “Remember my lovely slut, when you get to my door, you must strip bare ass naked. I don’t care who sees you. In fact, I suspect that exposure might just excite you. Completely naked, drop to your knees, resting your sexy ass back on your heels, head done with your hands, palms up, on your thighs. Don’t ring the bell; I will know when you are there.”
This may have excited me on some level, but the fear and sense of impending humiliation were overpowering. I got on the plane, took my first-class seat (thank you, Mistress), and immediately ordered a double scotch to help soothe the butterflies in my stomach.
When I arrived at the Miami airport, Jenny had a car and driver waiting for me, and it had a fully stocked bar. After another double scotch, I was almost ready for my naked presentation for Mistress Jenny.
After arriving at her house, the driver took my bags and deposited them at the door. I walked up the walkway on wobbly knees, and with a tear falling down my right eye, I slowly started to unzip my short skirt. Out of the corner of my eye, I saw several of her neighbors. I was trembling! Oh, Mistress, must I really do this?
I removed my skirt, and since my blouse was transparent, I hoped she would let this be enough. I fell to my knees, resting my hands on my thighs, and awaited my mistress. Waited, waited, and waited. Finally, after ten minutes, Jenny opened the door, not looking too pleased.
“What the hell is this? Didn’t I tell you I wanted you completely nude for this?” Jenny asked, irritated.
“Oh, Mistress, must I, really?” Tears were flowing from both eyes. “Mistress, your neighbors will see me. What if I get arrested?”
“Then I will bail you out, little one, but you have little to fear. This is Key Largo, after all. Now make yourself presentable.”
With that, you shut the door. I wanted to cry, but I slowly took my blouse off, reached my thumbs under the flimsy strings of my thong, and slip them over my hips, down my thighs, and of my legs, leaving them on her doorstep. Then I waited.
To be continued:
How long does Jenny leave outside on her knees?
What’s Sheri’s graduation surprise really look like?
