At forty-five years of age, I had finally come to the realization that spending only 4 months out of the year inside the comfort of my home was not the lifestyle I envisioned. I had built a successful international risk mitigation consulting firm. The problem with the international part of it was that most of my clients were in Europe. Flying from Seattle to London, Frankfurt, Berlin or Paris was not the shortest trip.
Four years prior, I had gotten to the point where I could fly first class, which made the 10-hour flights less frustrating, but the bigger my small company got, the more often those flights had to take place.
On my forty-fifth birthday, I was in Paris and my beautiful wife Anna surprised me at my hotel, wearing a trench coat and lingerie underneath. She granted my long-time bucket list wish of cumming on her face that night. I was so sexually backed up, that I covered her face and brown hair, before collapsing next to her with a smile on my face. Despite her thirty-seven years of age, she was more beautiful than most women I came across on a daily basis.
Our sex life was awesome when we were around each other. She was always the one to initiate and made me feel like a million bucks when she came each time. She never asked me if I remained faithful over the 16 years of marriage, but I could proudly say I did.
That surprise in Paris made me realize that I didn’t want to be away from her that often anymore. I decided that night that I would hire an executive that could go on some of the trips for me and I would focus on the big accounts. Since eighty percent of my income came from three clients, that would mean that I would only have to take about four trips to Europe per year.
It took me six months and about two dozen interviews to hire Jim, an eager thirty-five-year-old that had been working in the same industry for a major firm. I was able to offer him $250,000 a year and some retention bonuses on top of it.
We spent the next four weeks visiting all clients and going over the details of each contract. I knew I hired the right guy when he not only made great first impressions with all clients, but also provided great insight from day one.
I wanted to surprise Anna, by returning home from a trip three days early and tell her that my next trip probably would not need to happen for another few months. I booked a trip to Cabo San Lucas and was planning on giving Anna a day to pack.
Since she was a homemaker, enjoying the fruits of my labor, I knew there would be very little changes in her plans.
The driver pulled up to our Medina home and quickly noticed another car in the driveway. I didn’t think much of it at first, but the car was rather run down and had a bunch of crap inside. Instead of opening the garage, I opened the front door quietly and the moment I stepped in, my I nearly pissed my pants. I could clearly hear my wife moaning in pleasure. I walked down the hallway towards the large room we used as a home gym, and there she was, being fucked by a young-looking guy that I figured was her personal trainer.
I was about to grab the guy and choke him to death, but I decided to pull out my phone, take a few pictures and a video of them before sneaking back out again. My heart was racing, I was visibly shaking and, for the first time in my life, I was facing a stressful situation that I had no idea how to handle.
I called my best friend Dave and asked him to come pick me up. We headed to a bar in downtown Bellevue, and Dave did his best to calm me down.
“Let me ask you a question, and don’t get pissed off. Have you ever cheated on her?” he asked.
“No, I was naïve enough to turn away any of the advances over the years. Why?” I asked.
“Just making sure that you are not a hypocrite. I know you love her and, as a lawyer, I can tell you that despite the video you have, you are gonna lose a bunch if this ends up in divorce,” he explained.
Two beers later, it became clear that I wanted to make it work out, assuming that Anna wanted to as well.
“I sure as hell don’t want her not to pay for this somehow,” I said.
“Hear me out. What if you show her how it feels?” Dave said.
“What do you mean?” I asked.
His mind started racing: “You hire an escort. You and Anna decide to do some BDMS type shit and she gets handcuffed. Then walks in the escort and you show her the video that you took and fuck the babe in front of her. Hell, have her sit on a vibrator that will make her cum while she watches her husband sleep with another woman.”
I literally began visualizing the scenario. I pondered for a moment and told him that I thought I liked the idea. Dave bought me another beer and began to look online for some escort sites.
I needed a day to cool off so I did not tell Anna that I was stateside and spent the night at Dave’s instead. We went to the gym together and my anger allowed me to lift more weights than ever despite still feeling the effects from the beers and jetlag.
I was struggling with my last rep of bench press, when Dave, who was spotting me, greeted a woman and nearly caused me to drop the weight on myself. When I sat up, I could see the reason why he got so distracted.
He introduced me to Jen, a slender, tall, young blonde that had every genetic reason to only wear a sports bra and tight Gymshark leggings.
“Jen is the admin we just hired at the office,” Dave explained and we shook hands.
For the first time in a long time, I had no issue checking out another woman without a sense of guilt. I think she noticed my visual approval and she smiled in return.
“Are you going to Happy Hour after this?” Jen asked.
“Oh crap, I completely forgot about it. I can’t tonight, sorry,” Dave said, indirectly referring to my situation.
“Don’t cancel because of me,” I said.
“You can come too,” Jen said excitedly.
We agreed that we would head back to Dave’s place to get ready.
“She is gorgeous,” I said once we got to the car.
“I am not sure if she is trying to earn a bonus from the VPs, but she has sex appeal written all over her. She wears the shortest skirts and highest heels to the office. But, she is super professional so I don’t think any of the guys have tried to make a move,” he explained.
We got to the bar and true to Dave’s statement, there was Jen, wearing heels and a short skirt and blouse. Sitting on a bar stool disabled her choice to hide her sexy long legs. She reserved a seat to her right that I took and Dave sat across from her. We were joined by five more co-workers, most of which I knew already.
Two hours into the evening, the crowd size began to dwindle and Dave made sure to keep me liquored up. Jen turned out to be a light-weight and was visibly intoxicated.
After another thirty minutes, only Jen, Dave and I were left and out conversation switched to me.
“I see you are wearing a wedding ring, where is the wife?” she asked.
“At home,” I quickly said.
“Oh, I see, Everything ok at home?” she asked and leaned forward, revealing more of her cleavage.
“Jen, what the hell kind of question is that?” Dave chimed in.
“It’s ok Dave,” I answered. Without hesitation, I added: “I just got home from a business trip today and found my wife fuck her personal trainer.”
Dave was about to stop me, knowing it was the liquor that caused me to care less about divulging those details.
“I am so sorry. Did you beat up the guy?” she asked.
I told her the whole story and after she asked what I was going to do, Dave realized I was about to tell her about the plan with the escort.
“Dan!” he said, trying to stop me.
I didn’t care and told Jen about our plan. She paused for a moment after I was done.
“That sounds hot,” she said, and stroke my forearm. Dave rolled his eyes in response and suggested that we give her a ride home since she was in no condition to drive all the way to Tukwila.
“How much do you pay an escort to do something like this?” Jen asked when we were driving on the 405.
“Depends on how hot she is and what she is willing to do,” I answered.
Dave changed the topic and minutes later, we got to her apartment. I got out of the car and opened the door for Jen. I helped her out of the car and got a clear view of her white thong when she stepped out. She knew I saw it and made sure to get close to me when she stood up.
Smelling her perfume, feeling her breath on my ear and being that close to this babe gave me a sexual rush. I walked her to the front door, which gave us enough time for her to grab my phone number.
Dave apologized for her immature behavior, but I told him not to worry about.
I was climbing into the guest bed when my cell phone lit up. It was a message from Jen.
“Call me pls!”
I called her and she picked up right away.
“Hey there,” I said nervously.
“Hi there. I will do it, I will help out,” she said.
“Huh?” I asked confused.
“Let you fuck me in front of your wife,” she said bluntly. The vulgar, confident tone, gave me an immediate erection. I didn’t see a reason to turn down her offer, but had no idea how to respond.
“I saw the way you look at me, so I know that I meet the criteria. I can guarantee you that I could put on a show however you’d like,” she said, sounding like a salesperson.
“Why?” I managed to ask.
“You are hot, I always wanted to try something with someone twice my age and, well, I could use the money,” she said.
“I am not going to lie, that sounds very intriguing. How much did you have in mind?” I asked.
“Like you said, depends on what she is willing to do. I am not sure what that means, but I guess whatever pays the most,” she explained.
She explained to me that she was without a job for a few months coming out of college with a bunch of debt. The new job was ok, but it barely paid enough to pay her bills as it was. I tentatively agreed and we decided to meet for lunch. I canceled the trip to Cabo and had the hardest time falling asleep. My mind was bouncing from the memory of seeing Anna earlier that day to envisioning seeing her watch me with Jen.
I decided not to tell Dave about the meet and told him I might be gone by the time he came back from work. Jen lived up to her reputation when she walked into the restaurant in her professional, but very revealing outfit. Her heels, pantyhose and pencil skirt were black, and her top was a navy blue cotton looking sweater that made her tits look larger than usual . Her curly blonde hair reached far past her shoulders and her face exuded confidence that could not be mistaken.
During the meal, we finally got into more specifics. She seemed nervous about saying anything about the price, but she could have mentioned any number, and I would have agreed to it.
“How do you picture it? Picture me?” she asked.
“Hmm. Expensive lingerie, heels, stockings, maybe a collar around your neck. You are on your knees, sucking my cock, only feet away from my wife. You beg to have my fuck you and stuff like that,” I said, feeling myself get hard.
“That sounds hot. So, I did some research online. It seems like anal pays a lot. Would you want that too?” she asked.
“Uhm, never tried it. I guess. Have you done it?” I asked.
“No, but I have always wanted to. Here, look at this list,” she said, showing me a profile of a Russian escort that had all of the categories checked off. “I looked up what all of those things mean and I would be willing to do all of them.”
“She is listing her services for $1,800 for two hours. What were you thinking?” I asked.
“About that, but I guess we can negotiate if needed,” she said shily.
“I have a better offer. I did some research too and it seems impossible to find an escort to have sex with you without protection. How about we both get tested and I pay, you, let’s say, $4,000 to have sex with me without a condom?” I offered.
She nearly spit up her water. She tried to not sound too excited when she agreed.
We made arrangements to head to the clinic together after she was done with work and come up with more details then.
I was supposed to return Saturday afternoon and it was Wednesday. I figured I would have a hard time pretending everything was ok, so I decided to order some lingerie and BDMS supplies and have them shipped to our house. I would give Anna instructions to go to the spa that day, put on the lingerie I bought. I decided to get the identical lingerie for Jen and asked her if she wanted to go to the sex store near her apartment together.
After taking the tests, we took her car to Tukwila and spent a good hour at the sex store. We bought supplies to clean her ass, a plug and small dildo to loosen it. We also purchased some handcuffs, tassel whip, ball gags, large dildo, a magic wand vibrator and just as we were about to check out, I saw a BDMS set that was called a position master. It came with cuffs and an arched back forced posture kit, where a rope connected a neck collar and anal hook.
“Shit, that’s hot,” Jen said. The cashier suggested some over the counter dick enhancement pills that were supposed to keep me harder longer and last longer as well. I agreed and she wished us to have fun before we left.
Back in the car, Jen offered to stop by her apartment before she took me to Dave’s. I quickly accepted the invitation. I strategically walked behind her as we climbed the stairs to her second floor apartment, watching the epic view of the twenty-two-year-old’s nylon covered legs.
Her apartment was furnished very basic and when she opened the fridge to grab me a water bottle, I noticed that she barely had any groceries in stock.
“Now what?” I asked and put down the shopping bags.
Jen walked up to me, opened the water bottle and took a drink from it before handing it to me. As I began to take a drink, she got on her knees, and quickly unbuckled my pants.
“I figured I show you what I am capable of before you pay me,” she said and tugged on my boxers. “Yes!” she said, once my semi-erect cock came free. She wasted no time and put as much of me inside her mouth. By the time she bopped her head a third time, I was hard as a rock. I started to comb her hair with my hand and tugged on her head a little bit to pull her in more.
“He’s fucking big,” she said after struggling to take me all the way inside her throat.
Oddly enough, I compared her to Anna in that moment. I am not sure if it was my wife’s practice, on my cock or others, that made her a pro at deepthroating me fully.
Jen seemed determined though and ignored the drool that began to drip on her outfit. I did not take long for me to realize that I had not cummed in over ten days. I moaned and groaned, trying to find the right balance between pushing hard enough without taking it too far.
Each time I looked down and spurred her on with my comments of approval, she’d look up at me and essentially told me with her eyes that she’d do anything to please me.
She gave her jaw a break and stroked me feverishly while sucking on my balls. I replaced her hands with mine and pumped myself towards an impeding orgasm. I used my off-hand to push her farther down so her face was below the base of my cock.
“Cum on my face!” the young blonde begged, her left hand inside her pantyhose, stimulating her clit apparently.
I cried out, my frustrated body pushing out every drop of cum that had collected inside my aching balls. It was only my second facial in my lifetime, and it exceeded the first both in volume and degradability. When I finally looked at the mess I made, I saw the babe in shock, her eyes glued closed by my sperm, her lips completely covered in it, and if her shirt needed dry-cleaning, it would make for an awkward drop-off.
“Wow. I don’t even, what am I supposed to do with all of this,” she said through her cum-covered lips.
“First facial?” I asked.
“Hell no. But nothing like this,” she responded.
“Well, on Saturday, I will pay you to eat every drop of it,” I said. She got my hint and began to lick her lips. I was not sure if she cared about the texture or taste, but she obediently scooped whatever liquid was salvageable. Since she needed a shower, we decided for me to take an Uber.
We would come up with detailed plans as Saturday got closer. I had to pretend that I just woke up when I spoke to Anna and made it sound like I had to get going quickly. She seemed suspicious since we had not spoken in a couple of days. I told her I had something special planned Saturday and wait for instructions.
I ended up only texting her the rest of the week, including telling her to not open the Amazon package until the day I arrive. I declined her offer to pick me up and told her to make sure to be ready and have some fun. She seemed excited and with each passing hour, I was trying to imagine how I would feel when I first saw her.
When both Jen’s and my STD tests came back clear, I knew the plan was on.
Jen was to wait in her car and pull up when I texted her. At that point, Anna would already be cuffed and blindfolded. I was extremely nervous when Dave dropped me off at my house. I grabbed my luggage and he wished me good luck. I did not tell him what I was planning that night.
I instructed my wife to put on the heels, stockings and corset and wait for me inside our bedroom before I got there. I swallowed a couple of the pills that I purchased at the sex store before I walked in.
The moment I walked in, I noticed the red rose pedals that were leading from the front door up the stairs. For one brief moment, I felt guilty for hiring Jen. I even grew hard as I walked up the stairs, genuinely looking forward to seeing my hot wife dressed up for me.
She did not disappoint. About two dozen candles were lit and she was literally playing with her hairless pussy, legs spread wide, when I walked in. She greeted me mid-breath as her moans filled the air.
I placed the bag of toys at the foot of the bed and my first contact I made with my wife was sticking my middle and ring finger inside her pussy.
“Fuck, you are not messing around. I missed you too,” she said, trying to sit up to greet me with a kiss. I pushed her back on her back, however, and picked her up her 5’8″ body, 130 pound body to throw her closer to the head of the bed.
“Dan!” she exclaimed, surprised by the rough toss. I grabbed the handcuffs and blindfold and told her to close her eyes. I climbed next to her and when her right hand tried to reach for my hard cock, I swatted it away. She smiled, seemingly liking the scene as it unfolded so far. I placed one cuff around her slender wrist, noticing that she just got her nails down in a fiery red, wrapped the chain around the metal post that was part of the headboard, and cuffed her other wrist.
I placed the blindfold on her closed eyes before grabbing my phone to text Jen. I also decided that I wanted to record this so I put the phone on the window sill behind her. I grabbed the magic wand vibrator and pressed it against her sex. She jumped up and immediately began to moan.
“Is that for me?” she asked with a grateful tone. I decided not to answer. I transferred the video I took of Anna onto my iPad so she could see the evidence on a larger screen. The humming of the vibrator was loud enough for Jen to walk in undetected by my wife.
I scanned her body, dressed identical to my wife, from head to toe. Even the red fingernails matched. Her pussy was freshly shaven and the 6-inch heels made her 5’9″ body look astonishing. She placed a bag that she brought with her on the floor and quietly walked up to the right side of the bed.
Anna seemed to be getting close to an orgasm, so I quickly pulled the vibrator away and she complained, jokingly calling me a brat.
My hands were shaking when I climbed next to her. I pushed play on the twenty second video and the sound of my wife’s moaning and the guy’s body slamming against hers filled the room. Her smile quickly disappeared and by the time I removed the blindfold, her facial expression turned into a look of utter shock. She looked at the video, then at me, her eyes already watering up. She did not even realize that there was a woman standing on the other side.
“I, I, I,” she stuttered, her heart probably racing even faster because she was constrained.
“Pshhhh,” I told her and put my finger against her quivering lips. She then finally saw Jen.
“Who the hell is this? What is going on?” she said, freaking out even more, her arms flailing in their limited space.
“Anna, meet Jen,” I said. “Jen, I think she will have too many questions. Do you mind getting the ball-gag out of the bag for her?” I asked, not even looking at my wife. My wife looked at the hot babe in terror. When she came back, she was about to hand me the leather-strapped red ball, but I told her to put it on instead.
I watched as Jen placed the straps on her. She smiled at me a couple of times, which comforted me for some reason. Tears were streaming down Anna’s face by the time she was done. I had no specific agenda in mind, but I first wanted to see Jen eat out my wife.
Anna’s eyes opened wide when she heard my instructions. I did not ask if Jen had a thing for women, but lesbian was part of the listed services that she agreed to. As much as Anna tried to avoid it, she found pleasure in Jen’s skillful tongue. Watching the young babe on all fours made me want to taste her myself.
She was already wet herself when I stuck my tongue inside her sex. My nose pushed against her seemingly cleaned ass, the smell of soap filling my nostrils. I wanted to fuck this babe so I dropped my pants and began penetrating her within seconds. Anna was looking away, whenever she opened her eyes and I made sure that I was looking at her the whole time.
When she finally looked into my eyes, the utter terrified look made me feel guilty once again. I took out my guilty feeling by spanking Jen’s ass. I began to spank her harder to the point where my hand-prints were immediately visible. The paid babe did not fight back but kept pleasing my wife instead.
I recognized the look on Anna’s face that told me that she was about to cum, her nose barely being able to let enough oxygen into her lungs. I grabbed Jen by the hair and pulled her off, seeing my wife’s pink pussy completely soaked. My wife looked angry before looking away and then closing her eyes in frustration.
I grabbed Jen’s reddened ass and pushed her so she would be perpendicular to Anna. I stepped in front of her and made her suck my wet cock in clear view of Anna. Just like the other day, Jen wasn’t able to take me all the way and was soon gagging all over my cock as I pushed my way into her throat.
The sound of Jen’s gags and coughs got Anna’s attention and I wondered if she was thinking that the slut could not even suck me as good as she.
When Jen began to struggle too much and began to gag just by the touch of my cock on the back of her tongue, I decided it was time to raise the ante. I grabbed the key to the cuffs, told my wife to follow my directions, before taking off the constraints temporarily. I had a tight grip on her wrist when I forced her off the bed and onto her knees.
She then noticed the cell phone pointing right at it and was about to say something, but wisely kept her mouth shut probably fearing being ball gagged again.
“Grab the hook constraint,” I told Jen and in the meantime, I reattached the cuffs behind Anna’s back. Jen handed me the anal hook that had the chain attached and I signaled her to be the one to apply the neck collar. My wife nervously looked nervously at what we were up to so I blindfolded her momentarily.
I applied some lube to the stainless steel hook and told Jen to bend over in front of my wife’s face.
“Lick!” I said and pushed her head forward. Her face was far too low so I told her to get on her knees, giving me better access to her ass as well.
“I cannot hear anything Anna, get your tongue in there!” I said and whacked her ass, causing her to flinch. I poured some lube on my left fingers and the moment I got near her anus, she clamped up. She was about to pull her face back to say something but I used my other hand to push her face deeper into Jen’s crack.
Unsurprisingly, her ass was extremely tight. When I felt that enough lube had been applied, I just forced my middle finger as far as my hand would allow. I heard a muffled whine from my wife. Lucky for her, the hook was relatively small; about the girth of my finger and it went in relatively easy.
“How is she doing Jen?” I asked.
“I’ve had better,” she responded.
“Let’s go Anna. I paid her a lot of money so don’t let it go to waste,” I said.
With the hook in place, I connected the hook and collar via the chain the came with the kit. An additional clip enabled me to shorten the chain to the point where Anna’s back started arching.
She had been on her knees for a few minutes at that point and the only reason why her legs had not given out sooner was the tremendous shape she was in. The blindfold was wet when she got a moment to breathe and rest on her heels. I decided to provide my wife with a little comfort by grabbing a pillow and place it underneath her knees.
Still blindfolded, I stepped in front of Anna.
“Check this out Jen. Anna, be a good wife and show her how you can suck cock,” I said and waited for her to open her mouth.
“Open!” I said sternly and, ever so slowly, she did. Since her mouth had been gagged for minutes prior, it was wet enough to take me deep within seconds.
“Look at this,” I told Jen, who was standing next to me, her hand massaging my balls.
I grabbed my wife’s head and forced my way balls-deep. We had done it so many times, that not only has she perfected her skills taking me, but also my awareness of what her limits were.
“Shit, she’s a good little slut,” Jen said and for some reason I was a bit offended by her calling my wife that. But she was right, aside from cheating on my with her personal trainer, she was great in bed.
I removed the blindfold and purposefully began to make out with Jen. The young babe made sure to stretch out her tongue to penetrate my mouth repeatedly. I got lost in the moment and kept my cock shoved into Anna’s mouth for too long. She shook her head frantically and I pulled out. She coughed immediately.
“Oh, pour baby,” Jen said sarcastically. “Maybe your cock is too big for her after all.”
I let it go, even though I was not a fan of her belittling my wife. It only made me want to be more aggressive towards her.
“Get on your knees and see if you learned anything,” I said and I could have sworn I saw a grin on Anna’s face. Jen was not the biggest fan of what was happening next, but I could care less.
Both women ended up cheek to cheek and I began deepthroating Jen until her gag reflex rejected me within seconds. My cock was still covered in Jen’s slimy saliva when I shoved it into Anna’s throat. I repeated the process a few times, each break in between allowing me to regain my stamina.
In the end, both their mouths were covered in spit.
“Kiss each other,” I ordered and Anna remained frozen while Jen moved over and seductively kissed and licked my wife’s mouth. She looked at me with her hateful eyes as I enjoyed the show. When she finally closed her eyes, she actually began to kiss Jen back.
“Go clean your ass,” I said to Jen, and she grabbed the enema kit and went to the bathroom.
Once she was gone, Anna began to say. “Dan, please…,” but I told her to remain quiet and I helped her onto her feet. With the hook up her ass, she wasn’t quite able to stand up straight and when I led her to the edge of the bed so she could lean forward, I realized that either she would choke to death or her ass would rip out if the chain remained that short. I adjusted the length so she would only arch slightly. I paused for a moment to stick my cock up her pussy, thinking of the fact that another man was inside that body only days prior. I grabbed my phone and took a closer video of my wife’s behind.
I was overcome with my anger again and knew that I was not going to make love to her anytime soon. Instead, I fucked her as hard as I could the moment I penetrated her. I knew that she liked being taken that way but I didn’t know if having something up her ass and having her hands cuffed behind her back would have been a choice of hers.
I got close to cumming way too fast so I had to pull out. I think Anna was close to cumming herself, adding to her sexual frustration yet again. Without applying lube to it, I grabbed the dildo that was slightly larger than my cock and began to poke her pussy with it. She could not see how big it was, but the fact that it was harder, must have made it feel a lot bigger once I shoved it inside of her.
“Oh fuck Dan,” she moaned and I found a steady rhythm to piston the toy into her with. The view, captured by my phone, was epic. From the viewpoint, her stockings clad legs seemed to go on forever.
“Oh gaaawwwd,” she cried out when I kept up the pace. I knew she wanted to move her body around but the anal hook kept her movement very much in check. Jen finally returned.
“Let her lick her your ass to make sure that you are clean,” I said and she laid down in front of Anna and pulled her legs back so her ass rose off the bed. At that point, Anna was fully surrendered to my plans and began to lick the stranger’s ass.
I replaced the dildo with my cock and began to fuck her while watching, and recording, my wife licking another woman’s ass. I grabbed my wife’s wrists to get a better hold of her so I could drive into her harder.
I began to feel my sensation in my cock, which I attributed to the pills I took and I felt like I could last longer. Nonetheless, I would have to take a few breaks, primarily because my eyes were flooded with the beauty of two women and my cock driving into one of them.
“Fuck yourself with this!” I ordered Jen and handed her the dildo that still had my wife’s juices on it. She took a while to warm herself up to it, running it over her wet slit. I took it back out of her hand and reached over my wife’s hand and shoved the big dildo straight against Jen’s cervix.
“Fuck me,” she groaned gripping the bed sheets with her hands. I let her take the dildo into her own hands again and I gave Anna one final push against her head to make sure her face was pressed against her ass.
I had to take a break and took a step back. I had to admit that my wife looked as hot as the woman who was over 15 years younger. My love ran deep for her and I had to try hard to let my anger keep pushing me further that night.
My desire to move on was made easier by the fact that I was about to have anal sex for the first time. I grabbed the lube and walked up to Jen, pulled Anna aside so she was laying facing me and I pulled Jen around, so her ass was partially hanging off the bed.
I remembered that we got smaller toys to prep her ass for me, but I figured that we could try it without. Jen pulled out the dildo and I handed my phone to her, telling her to make sure not to miss the grand entrance.
Anna just laid there, motionless, watching me pour lube on my cock and getting into position to take another woman’s ass. She had always declined my suggestion to try anal. Now she about to witness her husband have his wish fulfilled by another woman.
I pushed some lube into Jen’s tight ass with my index finger. Since I could barely fit my second finger inside of her, I knew I would have to massage her sphincter for a while. I wasn’t sure if she was faking it, but Jen began to moan in pleasure. She was pinching her nipples through the corset and would occasionally rub her clit as well.
I added more lube a few more times before daring to poke her with my cock. It felt like I was pushing against a crevice without an opening at first. Once the tip made its way inside of her, her sphincter had a death grip on me. I must have not gotten farther than one inch for a least a couple of minutes.
Jen finally grabbed the back of her stockings clad knees and opened up wider for me. Surprisingly, I was able to push most of my length inside of her; Jen responded by holding her breath before exhaling loudly.
“Shit!” she said and raised her head to get a better look at my cock buried inside of her. I think Anna just realized that Jen was not a pro at it herself so I made sure she was aware.
“How does your first cock up your ass feel?” I asked.
“It fucking hurts, but I am loving it,” she groaned and was already playing with her clit again. I saw that Jen had put the phone down so I used that as an opportunity to get a bit rough with her.
“Who said you could put the phone down? Grab it!” I said sternly and Jen had to let go of one of her legs to pick up the phone next to her.
“You know you need to be punished, right?” I said, looking straight at her. She nodded nervously. I decided to slam my cock into her a few times, watching the lube covered rod piercing the young rectum.
“Fuck, me!” she yelled out, not as a request, but out of agony. Anna decided she had to look away so I grabbed her head and made sure she was facing the act only inches away. The tightness made me get close to an orgasm faster than I had wanted to. So I pulled out and since my hand was still behind Anna’s head, I instinctively moved my soiled cock straight towards her mouth.
She quickly turned her head away as hard as she could.
“Open!” I ordered in a tone that made sure she knew I was not willing to negotiate.
Ever so slowly, she parted her lips and I pushed onward before she opened wide enough for me to go past her teeth. Her disgust was unmistakable, when she closed her eyes and managed to let me force my way inside her throat.
“That’s so fucking hot!” Jen said excitedly with a smile on her face. “Good thing I cleaned my ass for her.”
“You can tell me how you did since you are next,” I said and her smile quickly faded. I pulled my cock out and since most of the lube was sucked up by Anna, I applied some more on myself and penetrated Jen’s ass again. She was still as tight as the first time, but any sense of nursing her hole had vanished. She was quickly in agony again but did not dare to tell me to stop. I was not interested in injuring her, so I was content when need to cum returned within seconds.
I pulled out, grabbed the phone out of her hair and told her to lay down next to my wife. I rolled Anna over so she was laying on her back, her hands awkwardly trapped by her body and a hook still up her ass. I hovered over their faces so my balls were hanging over Anna’s mouth and the tip of my cock was ready to be sucked by Jen.
Anna had to be told to begin licking my balls but Jen knew what she had to do. She allowed me to poke her cheek with my dirty cock and she happily licked the underside of it. I looked at my cell phone screen to make sure I had a good view of both women before I gave my cock a few more strokes to push me to the zenith.
I caught Jen off-guard when I shot cum against the inside of her cheek. I pulled out and back and began to shower both women with my semen. Jen played her part and smiled, accepting my degrading act with pleasure. Anna, on the other hand, kept her eyes closed and probably wished this was over sooner than later.
I squeezed out the last drops and let them fall right into Jen’s eager mouth.
“Don’t swallow!” I said. “My wife wants a taste of it as well.”
That comment made Anna’s eyes open wide and look at the lens of the camera sternly. Jen clearly enjoyed humiliating another woman and turned over so she could get her mouth over my wife’s.
My stern look back at Anna told her that she better open her mouth, so she did. My wife was not too turned off by my cum usually. But receiving it from another woman’s mouth was probably not on her bucket list. She gagged when the cum and saliva combo rolled to the back of her mouth.
“Make out!” I said and Jen lowered her mouth, grabbed Anna’s face and shoved her tongue inside her. I took a step back and got a full-frame recording of the two women kissing each other with my cum getting passed around.
Since my orgasm drained any sexual desire and energy that I had left, a sense of guilt rushed into my brain. I quickly opened the safe, grabbed the money for Jen and told her to get changed and cleaned up in the bathroom.
Anna remained quiet while I took the hook out of her ass, fecal residue coming along with it, and took off the cuffs. I kept on her lingerie and heels.
“How long have you been fucking other men?” I asked, breaking the silence.
“Dan, I am so sorry,” she said, tears streaming down her face.
“How long?” I asked again.
“With Jim since January,” she stuttered.
“There were others?” I asked, feeling my anger rise to new heights.
“Two years ago, there was a guy, we only did it once,” she claimed.
“Do I know him?” I asked.
“Dan, please,” she said, but she knew I expected an answer.
“It was Dave, you and I fought and one thing led to another. I am so sorry,” she said contritely.
“That motherf…,” I felt nearly as betrayed by him than by my wife.
“How many times did you do the trainer?” I continued the interrogation.
She thought about it for a moment, and I realized that she was building up the courage to be completely honest.
“January was the first time and I felt so guilty so I turned him away until last month. We have done it each session since,” she admitted, her voice shaking.
“That’s twice a week!” I pointed out the obvious.
Jen interrupted our conversation and I thanked her and asked her to leave.
“You know what’s really messed up? I felt guilty for what we just did. Part of me tells me that I shouldn’t feel that way since I have never cheated on you my whole life. I still love you and want to make this work out, if you still love me,” I said, and she quickly chimed in.
“I love you Dan. I am so sorry,” she apologized again.
“Good news is that I am barely going to be traveling. Bad news for you, Anna, is that tonight was not the last time we did this. You are going to let me fuck another woman for each time that you let another man stick their cock up your shameless pussy, understood?” I said sternly.
“Yes Dan,” she said, and I believed that she would not put up too big of a fight.
“Let me wash myself and then you will get me hard again with your pretty mouth before you will beg me to make love to you,” I said and oddly enough, she smiled at that suggestion.
I took a quick piss, washed my cock with warm water and returned to the bedroom to find Anna already on her knees. I grew harder by the time I got in front of her and was shoving a fully erect cock down her throat one minute later.
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