Mother-In-Law Gets Her Way Again

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Heather put on a very skimpy red dress that hugged her body nicely. She was making her intentions very clear that she was expecting great sex when we got back to the room. We both knew we had our best sex on vacation, but unfortunately she wasn't the one I really wanted to have sex with on this one. Still, as good as she looked in that dress though, I knew I wasn't going to be too upset by having to settle on having sex with my wife. I pulled on my sport jacket and slipped the room key into my pocket. I held open the door for her, mostly so I could look at her ass as I walked out the door. It really was a nice dress.

When we got to the dining room at the resort, we found Evelyn, and to our surprise she wasn't alone at the table. A well-dressed gentleman was sitting next to her and they were laughing at something he had said just before we walked up. He was sitting but I could still tell he was taller than me. He had a good mix of grey and brown hair and a well-trimmed salt and pepper beard. I was jealous of him almost immediately, because he could openly flirt with Evelyn and I couldn't. However, I really couldn't let on that I was jealous, so I introduced myself and acted like he was my new pal.

In all actually he was kind of a fun guy once we got to know him. His wife had recently passed away from pancreatic cancer. They had already booked the trip when the cancer was discovered, and five months later she had passed away. So he decided to go anyway as some kind of farewell trip. I quickly realized I had nothing to be jealous about. He wasn't trying to hook up with Evelyn at all. He did start to inquire about the three of us though.

"Do you typically take your mother with you when you two go on vacation?" he asked.

"Oh heavens no," Evelyn replied for us. "I think my daughter felt sorry for me and thought this trip would bring me some joy again."

"Yes, it was my wife's idea, but I think Evelyn brightens any room she's in," I said. "I thought it was a fantastic idea."

"Hmm, that's interesting," he said.

"They have been so good to me since my divorce, Evelyn said. "I've really needed their love and support."

"Love and support you say," he said. "Because of your divorce? That's completely understandable. For a moment I was thinking it was one of those Sportsman's Double type scenario."

"Sportsman's Double?" I asked. "That's not something I'm familiar with."

"Yeah, me neither," Heather said, looking at Evelyn who seemed to know exactly what he was referring to. "Mom, you seem to know a little about it though. Please, do share."

"I can assure you that is certainly not the case here," Evelyn said.

"That doesn't help us mom," Heather said. "Is it some old time saying from way back when you were a teenager or something?"

"Oh I think it's older than that," he said, chuckling. "A Sportsman's Double to put it frankly is when a mother and daughter share the same man."

I had just taken a sip of water when he said it, and I actually spit a little out hearing the words. For a moment I panicked thinking somehow he knew Evelyn and I were fucking. Then I thought perhaps she told him before we got to the table, but that wouldn't make sense. No way she shares that intimate information with a total stranger who's about to meet me. Then I thought he must have made it up.

"That isn't really a thing is it?" I asked. "I mean you just made it up to pull our leg a little, didn't you?"

"Oh I didn't make it up," he said. "It actually happens."

"Apparently it happens often enough they gave it a name," Heather said laughing.

"Well I can assure you that is definitely not what we are doing here," Evelyn said. "Now let's order another round of drinks and enjoy the music."

We did just that. Spent the next couple of hours drinking, laughing, and dancing. Our new friend danced with Evelyn while Heather and I danced, and then we'd swap and I would dance with Evelyn while he danced with Heather. Eventually our new friend decided to call it a night. He thanked us for being such fun company for the evening and wished us all the best. We wished him the best as well and he walked away with one final wave. The three of us kept our own little party going, until Evelyn said she was ready to call it a night. I knew Heather was horny, because she is always horny when she drinks, and we had a hotel room. I think she gets off making the people in the next room jealous that we're having such great sex.

We all three made our way to the elevator. We all had drank our fair share, but I wouldn't say any of us were out of control drunk by any means. We made it to the elevator and on it with no problems at all.

"So mom, you sure knew a lot about that whole Sportsman's Double thing he was talking about," she said. "How did you know about it?"

"Oh honey, it's just something I remember reading about once when I was younger," she replied.

"So you and grandma never doubled up on dad or anything like that?" She asked while giggling. I was certain she was joking though.

"No dear, of course not," she replied. "You know your grandmother never would have done anything so scandalous or wild."

"Oh and you would?" asked Heather.

"Well, I'm not saying that, but between the two of us I was much more fun than your grandmother," Evelyn responded.

The elevator reached our floor and we all walked through the doors and into the hallway. I was a little disappointed I hadn't found a way to sneak off with Evelyn, but actually a little excited for the great sex I knew I was about to have with my wife. We reached our door and I pulled my room card out of my pocket, and put my arms out to give Evelyn a hug goodnight. Instead of hugging me, however, she planted a kiss straight on my lips. It wasn't a passionate or intimate kiss, more like a goodbye kiss, but it caught me off guard none the less. I turned to unlock the door and Heather put her hand on my chest. She bit her lower lip and gave me her best "I'm so fucking horny" look.

"I think we should do it," she said.

"Do what?" both Evelyn and I asked simultaneously.

"The Sportsman's Double," she replied. As she said it, she slid her hand down my chest, over my belt, turned her hand and slid her fingers around my bulge in my pants. Looking Evelyn in the eyes she said, "I've seen the way he looks at you, so I know he would love it. Besides, were far away from home where nobody knows us."

I looked at Evelyn and I was surprised to see she looked like she was actually considering it. I must have looked like a little boy who just asked for ice cream and was pleading with my facial expression for her to say yes.

"Mom, I've also seen the way you look at him," she said. "I've known you wanted him since my wedding day, and here is your chance to have him. He's clearly up for it." She gestured down to fully erect cock sticking out inside my pants. "Come on, we can take care of him together."

To my complete surprise Evelyn put her key card back in her clutch and stepped towards us. I couldn't get the damn door open fast enough. I had to try three times before I saw the little green light and heard the door unlock. Then I pushed the door open and held it open for the women, and as usual I looked at both of their asses as they walked past me.

I couldn't really say what my emotional state was at that moment. The horny guy part of my brain was super turned on by the thought of having a three-sum with two very sexy women. The sneaky cheating husband part of my brain was a little nervous about combining sex with my wife and my mistress; who happened to also be her mom. The plain old husband part of my brain felt like I was walking into a trap, and should abort the mission immediately. Ultimately, I decided the worst-case scenario, it's a trap and Heather will use it to leave me; freeing me up to be with Evelyn. Best-case scenario, I get to have a three-sum with my two favorite women to have sex with.

Once in the room I took off my jacket and draped it over the closest chair I could find. I was really hoping they weren't waiting on me to get things going. This whole thing was Heather's idea, so I assumed she would take charge. When I looked at Evelyn, she looked a little nervous. It was clear she was waiting to see what should happen next as well. When I looked at Heather, she looked as cool as could be.

She walked over to the bed, stopped and turned, looked me right in the eyes, and motioned for me to come over to her. I started pulling my tie off and walked to her. Once I was standing in front of her, she reached both her arms up over my shoulders and behind my neck, leaned in and kissed me. It was a deep open mouth kiss and our tongues slipped all over each other. Then she dropped to her knees and motioned for Evelyn to join us as she did. Up until that moment I was still concerned it could be a trap, but then she unbuckled my belt, unbuttoned my slacks, pulled the zipper down, reached into my boxers, and pulled my cock out.

Evelyn walked right up to me and pressed her lips to mine. We kissed deeply and passionately, just how I'd wanted to kiss her the whole time we had been on the trip. While I kissed her I reached back and unzipped her dress, and pulled it down her her body as far as I could reach; letting it fall to the floor around her shoes. Then I unhooked her bra and pulled it off. Doing it all while we kissed and Heather sucked my cock.

I reached my left down and placed it on the back of Heather's head and my right hand reached up and began massaging Evelyn's left breast. I broke our kiss and leaned my head down, taking her nipple between my lips. I sucked gently and slid the tip of my tongue all over her nipple. Evelyn started unbuttoning my shirt while I massaged, licked, and sucked her breast. After the last button she pulled my shirt open and down my arms. I stood up straight and pulled the shirt over my wrists, and then pulled off my white undershirt over my head.

Heather pulled my pants down and I fumbled my way out of my shoes, using the toe of one shoe to push down the heel of the other. Once my shoes were off, I stepped out of my pants and she pulled my socks off. Then she stood up, turned her back to me, and I unzipped her dress. I pulled it down and let it drop to the floor as well. Then unbuckled her bra and pulled it down her arms. She pulled her panties off as she turned back to me.

"Lay down on the bed baby," she said, and I didn't even hesitate.

I sat on the edge of the bed and then leaned back as I scooted to the middle of the bed. Heather crawled onto the bed first, and straddled my waist with her back to me. For a moment I watched her reach down and guide my erection into her pussy as she lowered herself down over me. I only got to watch her amazing ass move over my cock for a moment before my view was blocked by Evelyn as she sat on my chest.

This was a position Evelyn and I were very familiar with. I knew just how she liked to be licked when she sat on my chest like that. Usually she would have been reaching back and stroking my cock, but since Heather was riding it, she reached both hands down behind my head and pulled my face to her pussy. I reached both my hands up to her breasts and massaged them while my tongue worked on her pussy.

Heather rode my cock and Evelyn rode my face for quite some time. I could tell Heather was close to her first orgasm by the increased volume of her moaning, and her deep breathing between each moan. I'm not sure if it was due to Heather's increased moaning or if my tongue was just hitting her perfectly, but about that same time I felt her thighs begin to shake as she had her first orgasmic wave rush over her body. I kept licking her pussy from the bottom to her clit until she stopped shaking, and then a little more just because I enjoy it so much.

Once Heather had regained her composure from her orgasm, she climbed off my cock. To my surprise she leaned down and wrapped her lips around my cock. She had never done that before in our four years of marriage. She wouldn't even kiss me after I'd gone down on her, so her doing anything that would lead to her tasting her own pussy juices shocked me. She didn't suck my cock long, pulling up as soon as Evelyn started moving towards her.

Evelyn must have realized Heather was finished and she wanted a turn as well. She just crawled down my body until she was over my waist, reached down, and then lowered her pussy over my cock. Just like her daughter had done to me earlier. She started riding my cock nice and slow at first, but quickly picked up the pace as she went. Then Heather completely shocked me again. She crawled up the bed, leaned in towards me, and started tongue kissing me.

She had to be able to taste her mom's pussy juices on my lips. Here is the same woman who wouldn't kiss me after oral sex with her, because she didn't want to taste herself, now kissing me with my face covered in her mom's juices. It caught me completely off guard, but I thought it was so incredibly hot. After she kissed me for a few minutes, she sat up and moved to the end of the bed. Then she just watched her mom ride her husband's cock for a few minutes.

I could see her watching us but I couldn't tell what she was thinking. She didn't look jealous or upset at all. Then I realized she was rubbing her pussy while she watched us. Once I knew she was getting off watching us, I decided to give her something sexy to watch. I put my hand on Evelyn's shoulder to let her know my intentions, and she picked up on it right away. She moved off of me and I sat up quickly, moving her to the edge of the bed just in front of Heather. I quickly hopped off the bed and moved between her legs, pulling her right leg over my left shoulder. I lined my cock up with her pussy and drove it straight in, going deep with my first stroke.

Once I started pumping my cock into Evelyn's pussy, I could see Heather really start to rub her pussy nice and good. I pulled on Evelyn's thigh to get leverage to really pound my cock in and out of her wet pussy. I reached down rubbed her clit with my thumb and kept pumping my cock in and out. Between fucking Evelyn so good and watching Heather finger her own pussy, I was finally on the verge of cumming. I think being so occupied with trying to please two women, my mind didn't allow me to get too aroused. Since it was just me fucking Evelyn and watching Heather as well, my mind got there in a hurry.

As I was pumping my cock into Evelyn, and knew I was getting real close, I remembered her licking my cum off her hand on the airplane. I quickly pulled my cock out of her pussy and moved along the side of the bed until my cock was right in front of her mouth. She didn't hesitate at all to grab it and wrap her lips around the head, just in time for me to blow my load in her mouth. She didn't even flinch and swallowed every drop that rushed into her mouth. Then she sucked and licked my cock clean, and even licked her lips when she was all finished.

The sight of her mom taking my load in her mouth must have really excited Heather, because her loud moan drew both our attention her way; just in time for us to watch her body shake from another orgasm. I crawled onto the bed and moved to the very middle, and tucked a pillow under the back of my head. Heather laid down next to me, and I pulled my left arm around her. Evelyn scooted up next to me on the other side and I pulled my right arm around her. For several minutes we just laid there in silence, but it wasn't awkward or uncomfortable at all. In fact, it was quite the opposite.

"We really do have our best sex on our vacations," Heather said. She raised her chin off my shoulder and gave me a kiss.

"Well hell, now I wish I would have tagged along with you two sooner," Evelyn chimed in. She also raised her chin off my other shoulder and gave me a kiss as well.

A few moments later I noticed both of them had fallen asleep. I just savored the moment for a little bit, while holding both of them in my arms. I knew Evelyn didn't feel the same emotional bond towards me that I felt for her, but at that moment holding her felt so right. But it didn't mean holding my wife felt wrong at all either. I just hoped when Heather woke up, she wouldn't freak out. A few moments later I joined them in their slumber.

I was groggy at first, and honestly thought I was still dreaming when I began to wake up. I could see the night sky was still dark through the window, so I knew it was the middle of the night, but the soft warm sensation over my cock was unmistakable. I looked down and I saw Evelyn's lips sliding up and down my shaft. While I thought it was a fantastic way to wake up, I still had to take a moment to put it all together. I glanced over at the clock, which read 2:39am, and realized we all had fallen asleep with the lights still on. Then I remembered the three-sum. I looked over and Heather was now laying on her left side, with her back to us.

I looked back down and continued to watch Evelyn suck my cock. God it felt good, and it was by far the best way any mom had ever woke me up. After her lips slid most of the way down my shaft and then back up, she opened her eyes and saw I was looking at her. She lifted her head, pulling her lips away from my cock and gave me a smile.

"Good, you're awake now," she said. Then she started crawling up the bed, straddling my body as she did it. "I had to make sure last night wasn't a dream, or some kind of alcohol induced hallucination."

She laid down on top of me, with her breasts pressed against my chest. She pressed her lips to my mine and we started kissing. It was another deep and passionate kiss, only this time it really felt to me like she was trying to tell me how close she felt to me through her kiss. Our tongues slid over one another's over and over again. I wrapped my arms around her and held her tight while we kissed, and she let out a little moan of approval while we kissed.

Then I felt her lift her lower body up slightly and felt her hand slide between us just below my abdomen. I felt her fingers on my erection and she moved it just enough to line it up with her pussy. Without breaking the kiss at all, she pulled the head of my cock into her pussy and lowered her pussy down over my shaft. She started moving her hips slowly, sliding her pussy up and down my shaft while we continued to kiss passionately. At that moment I felt more connected to her than I had to any other woman in my life.

My arms were still wrapped around her, holding her while we made love. I could feel her breasts against my chest, and her arms wrapped under my shoulders holding me as well. We both started to breath heavier, but Evelyn continued to kiss me while slowly sliding her pussy up and down my erection. I was a little nervous it might screw up the moment, but I started pushing my hips up slightly when Evelyn would lower hers. She appeared to pick up on it and started moving her own hips a little faster.

I released the boa constrictor grip my arms had around her, and she pushed up onto her elbows. She was still kissing me but she started to move her whole body on top of me, and actually started riding my cock. That only lasted a few more minutes before she had to pull her lips away to breathe heavily. She also started moaning quietly while moving her body up and down over me. I moved my hands to her breasts and I was finally able to watch her ride my cock. I was glad we had all fallen asleep with the lights on.

Her moaning started to get a little louder and her body started moving even faster on top of me. Her pussy was sliding up and down my cock at a good pace, and I was pushing my hips up to match her stroke for stroke. I could feel myself inching closer and closer to my orgasm and, judging by Evelyn's moaning and breathing, she must have been getting close as well. After only a few more strokes of my cock she threw her head back, and I felt the familiar shaking of her thighs as her orgasmic wave overtook her body. That was as much as I could take and I felt my own orgasm force its way through. I pushed my cock deep inside her and felt my cum gush out inside her pussy. My body twitched slightly each time my cum gushed out of my erection inside her.