*Names have been changed. This took place a couple years ago. This is about cheating. Not your thing, I understand. Please just move on.* 😊
My wife’s sister Janie is older by two years, and is very controlling. She’s a redhead who is on her second marriage after her first husband left, partially because of that.
Janie and my wife Meg used to look more alike back in the day but now Janie has gained some pounds and seemingly quit trying. Her second husband is massive and while a nice guy, is morbidly obese.
A couple summers ago, the four of us were supposed to go on a quick trip up to Wisconsin to a lake house. One of those picture postcard locations along the water where it was warm during the day, but the evenings were nice and cool. About a month before we were supposed to go, her husband Lenny hurt himself and had to have surgery on his knee.
Janie took care of him, nursing back to pretty good shape relatively speaking, but he wasn’t gonna be able to come. At first, we thought Janie was gonna bail but in the end she decided she was gonna go and have a good weekend away as she was a bit burned out on being a nurse for him for so long.
So we all jumped in our car and drove about five hours north. I did all the driving while Janie and my wife Meg chatted. Meg sat up front with me while Janie was behind Meg as there was more legroom.
Now I see Janie a couple times a week and as mentioned, she doesn’t really try to make herself up much anymore. I know that’s a bad thing to say, and I apologize if I offend anybody with that, but I’m saying that to help set the situation here.
As we drove, I would occasionally look over at Meg and then Janie in the backseat behind her as we talked about different things. Janie definitely had more makeup on that day than I was used to seeing her normally. I also noticed that with her weight gain her breasts had become much much bigger than I remembered.
She also was wearing a T-shirt from about a size ago at least and her massive breasts and big bra were now pushing that out. As I would talk to her or glance back at her in the rearview mirror, I started becoming fixated with the size of her breasts.
She had a crewneck T-shirt on, so it wasn’t like there was cleavage, but damn even in the rearview mirror those things looked large. And more than once, I think she noticed my gaze even tho I had sunglasses on.
At one point, I even drifted off a bit with some of my thoughts and found myself with half a chubby, and had to discreetly reposition myself as my shorts weren’t going to hide it very well. Luckily Meg was busy talking to Janie and didn’t notice.
We finally got to the cabin on the lake and settled in. It was a three bedroom actually, so plenty of space for us to all spread out and not be on top of each other for the four-day weekend.
Two rooms downstairs and then one upstairs. We took the upstairs one, tucked in the back of the house, while Janie took the bigger front bedroom. Her room had a bathroom it shared with bedroom two.
Janie and Meg decided they were gonna go immediately down to the common pool for the little neighborhood. So within 20 minutes of arriving Janie now walked out in a swimsuit, that just like the T-shirt was definitely a size too small.
An unlike the crewneck T-shirt, this swimsuit definitely showed cleavage and honestly even a little bit of side boob. When Meg came out from getting changed, I could instantly look at her reaction on her face to know she was a bit horrified at how much Janie was spilling out, especially up top. Even her butt was showing a bit more cheek.
I’m a sucker for cleavage so I was enjoying the show and even her ass, while clearly bigger than it should be was looking sexy to me.
I’ve never really even thought about Janie sexually because most of the time I had known her she just didn’t try, even when she was with her first husband. But today with lip gloss and eyeliner and her hair nicely done and now with the tight swimsuit, she caught my eye.
I had to look away or my crotch was gonna start reacting again. I kissed Meg goodbye as they left and watched them walk away, enjoying the view of both of their asses.
Once I saw that they were gone I went into our room to unpack. But the thought of both girls, especially Janie with her big boobs spilling out, got to me. I ended up jerking off in the bathroom, thinking about wanting to cum on her tits.
As I cranked myself, I wondered if her nipples were like Megs and responded to touch by getting very hard? Or were they the kind that I found many redheads to have where they didn’t really get hard. No matter how excited they got, the nipples wouldn’t get hard.
I soon found myself cumming into the toilet bowl, relieving leaving some of my tension and helping me become more relaxed and focus on unpacking.
While the girls were at the pool, I went food shopping and picked up each one of our favorites drinks for the weekend. By the time the girls came back I had grilled up some fish and some other side dishes. They wowed at my chef skills and enjoyed the meal. We all had a couple drinks each and by nine, both Jeanie and Meg were heading to bed.
I was ready to go party but being Thursday night nothing big was really happening yet so I just settled in the family room and watched TV.
About 10:30 I heard Janie‘s bedroom door open around the corner and she came plotting out to get some water. She joked about being dehydrated from having too many drinks but thanked me again for dinner.
Then she dropped a little bombshell.
“I saw you enjoying the view today, both in the car, and especially when I came out my swimsuit. I felt a little self-conscious when I put it on, but when I saw how you looked at me, it made me feel more comfortable. Thank you for doing that“
She walked towards me from the kitchen as I laid on the couch watching her. She had on a long t-shirt, most likely no bra and not sure about panties.
I kind of gave an innocent look and started to say something to defend myself, but she cut me off.
“It’s ok. I really appreciate someone looking at me with some level of desire, it’s been awhile.”
I knew she and Lenny had not had sex in over a year, maybe even two at this point. He was too self conscious about his weight and lack of mobility in bed. Her offers to ride him as an alternative went without acceptance. His cubicle job left him with very little exercise and he’d become a lump.
She put the water glass on the table, took a deep breath and without a missing a beat, pulled her night shirt over her head and stood before me completely nude!
Any question in my mind to what Janie’s breasts looked like and how massive they were when unrestrained by a bra or swimsuit, was now answered.
She was pale like a red head and her nipples stayed flat, despite obvious excitement. Her pussy was very trimmed to my surprise but still in her 50’s showed flashes of her red public hair. She had a pooch belly but it wasn’t much, especially given she’d had four kids with her first husband. Her hips were wide but it played well.
She was flush from excitement, a little bit of embarrassment and probably now holding her breath to see my reaction. And while I contemplated what I should say, let alone do, I couldn’t take my eyes off her breasts.
They were huge. I kid you not, seemingly twice the size of Meg’s.
“Wow, you look amazing Janie. I wasn’t trying to stare today but it was hard to not notice how nice you looked.”
She purred and then started massaging her breasts. She lifted each one and played with them. Then one hand dropped to her pussy and she started to finger herself. I didn’t know what to do.
Janie is normally very reserved in this area and she is very religious. The idea of her standing naked in front of her sister’s husband and playing herself was not on the proverbial bingo card, as the worn out expression goes.
I was dumbfounded but also turned on by the show. I decided to see where she was taking this and make a decision. I didn’t move. I kept watching. I’d paid her a compliment and the next move was hers, and then I had to decide.
She stepped closer towards me, and now I could smell her excitement. Her musk filled my nose and I could see her glistening pussy lips as she continued playing with herself. Little moans escaped her mouth and her eyes alternating between being closed with pleasure and staring down at me.
Finally, she was fully in front of me. I had propped myself on my elbow but had remained largely still. Her pussy was now basically in front of my face. I could smell nothing else but her. It was intoxicating.
I sat up and positioned my legs to the outside of hers. I looked up at her and she was staring at me. Upstairs, my wife/her sister snored as she slept. Down here, Janie was making herself clear what she wanted.
“I need this. I’m so sorry to put you in this position but I need you to…to…to…well you know.”
She had been very bold but despite standing mere inches away from me, completely naked and fingering herself, she couldn’t find the courage to say “I want you to fuck me”.
I’ve had many adventures but this was not one I’d ever thought of. I kind of felt trapped at this point.
Those big ol’ breasts were just calling my name. Big tits hanging there, ready to be kissed. Her pussy, long denied any pleasure from someone else, was wet and waiting for me to penetrate.
And my own cock had betrayed me, as it was hard as a rock. I’d come downstairs to watch tv in my sleep shorts and boxers, and both were strained. Janie looked down and saw this. She saw my bulge, my outline.
“You know Meg is to blame for this. She always talks about how much you make her cum in bed, how much she screams as you fuck her. I’ve had to listen to that for years while I got nothing. Please.”
Now, Janie has no idea of my adventures over the years, so in her mind she is asking me to do this for the first time. I had to make her think this was new to me.
“Janie, you are tempting me like I’ve never been tempted before. Your boobs, your pussy…it’s all intoxicating. But we can’t do this no matter how sexy you are right now to me. I think we’ll regret this in the morning.”
I’d said my peace. I’d said my resistance. Now what would she do.
I quickly got my answer as she stepped forward and grabbed my head, pulling me into her pussy. My lips were crushed up against her mound but I still resisted.
“I need this. I’m going to be selfish tonight. I will make peace with this in my own way. I will make it up to her and I promise I will never tell a soul.”
I pulled back and looked up at her. She had a resolute look on her face. She smiled down at me.
I stood up, took her hand that she’d been fingering herself with and licked it clean. She melted into my arms and we kissed. Our tongues immediately battled for position. My hands went to her massive breasts - the object of my obsession all day - and I kneaded them as we kissed.
I pulled back after a minute, and said once again no one could know. She couldn’t tell anyone, especially girlfriends. I would deny it and folks would believe me as I have somehow kept my golden boy image.
She agreed.
I took her by the hand and led her back to her room around the corner. We barely got into the room and the door closed before she pull my shorts and boxers down. My cock sprung out and Janie pushed me to the beds edge. She sunk to her knees and took my cock into her mouth.
While her sister did not like giving blowjobs, Janie’s first husband had disclosed to me years ago how good Janie was at giving them. I’d forgotten all about it but now his words came flooding back as she worked my cock with her mouth, lips and tongue. She liked to scrape ever so slightly with her front teeth as she pulled back.
I then noticed the glaze of her lip gloss being left on my cock as worked in and out of her mouth. But I’d seen her before she went to bed the first time and she had removed all her makeup. It dawned on me that she had reapplied her lip gloss and makeup before coming out to me in the family room. She’d 100% come out there to seduce me!
Emboldened with this realization, I grabbed onto her blazing red head of hair and started to face fuck her. I’d decided I was going the rough route with her tonight. She’d aggressively come after me, so I was going to put aside gentle lovemaking in lieu of an absolute hard fucking.
Despite having cum a few hours earlier, after just a few minutes I was tingling. I tried to be quiet but I started slamming into Janie’s mouth, to the back of her throat. She gagged of course but I didn’t let up.
I held her head even tighter as my cock grew even bigger and harder, the head swelling up just before I blew my load down her throat. I pushed all the way and she gagged. But to her credit, she took most of it.
I was breathing hard. That is not my normal style to go that hard but it felt great. She licked up the remnants of my cum off my cock and made a big deal about it. She looked up at me, eyes watering and makeup running from the gagging and smiled.
“I hope you’re not going to fall asleep on me like a normal man. I need you inside me.”
I took her hand and led her to the bed. She lay down and I followed her. I went down on her, spreading her legs and softly fingering her. Her moans followed immediately and only got louder when I added my tongue to the mix. She was sopping wet.
Meg is the same after the rare times she gives me oral. She claims not to like it but it gets her very wet. And now I knew her sister was the same!
I continued licking her lips while picking up the pace with my finger sliding in and out of her. Her moans became problematic and I stopped to give her the look.
She smiled again and dramatically acted like she was sealing her lips, locking them and throwing away the key. I chuckled at this and went back to business on her pussy. She compensated by putting a pillow over her face.
And then it started. A series of one orgasm after another. She was writhing on the bed as my fingers flew in and out of her and my tongue pressed on her clit. She finally had to tap out after a few minutes of this, sweat beading on her forehead and her pale body glistening.
“Please fuck me. Oh my god, please get inside me now. I will do anything for you after tonight as thanks. Please.”
I honestly felt bad for her. She’d been long denied and clearly enjoyed sex.
I pulled myself up from her pussy and looked down at her as she lay there. Her massive tits were flopped off to the side, her soft belly moving with her quick breaths from the excitement. Her pussy glistened even more than before, and my hard cock now poised at her entrance.
It’s a weird algorithm in my head of why but I didn’t want to fuck Janie raw. But I seriously doubted she had condoms. But I asked anyway to again play the part of the inexperienced cheater.
“For gods sakes Ken, I haven’t had sex in almost two years. I’m clean. Please fuck me,” she whispered insistently.
With that, I pushed inside my sister-in-law. By her own admission, no man had been there for almost two years. She was tighter than I expected given she had four kids, all naturally. I know they say the vagina rebounds but still, she had three very large boys travel thru there back in the day, plus her daughter.
Despite her obvious excitement and having cum a few times already, I had to work into her still. But I finally hit bottom and was soon building up a rhythm. Her soft mound was the perfect backstop to my pumps into her.
I looked down and enjoyed the sight of my cock working in and out of Janie. I looked at her and she was also looking down at me going in and out of her. She played with her large breasts, tweaking her flat nipples. Her moans were getting loud, so I leaned down and took her back into my mouth.
She easily accepted me and now the attack angle was different as continued pumping into her. She whispered into my ear how good it felt and then bit her lip trying remain quiet as she came on my cock for the first time.
Her arms wrapped me and held tight as she rode the orgasm. Then she started giving me directions on she wanted me to fuck her. Not just the standard “right there” or “that feels good like that”.
No, she was telling to raise myself up three inches and don’t pull almost all the way out, just short strokes when I was basically balls deep in her. As I said, she is a bit controlling. And while I wouldn’t exactly call this a mercy fuck, she didn’t fit the normal definition of women I’m with.
Thus, after a minute of this, I grabbed her and flipped us around. She was in top now, riding me.
“You set the pace Janie. You fuck me now how you want it,” I said quietly but with authority.
She smiled and immediately put her big ass in motion on top of my cock. Our bodies slapped together as she rode me. We held hands as I supported her as she fucked me from above. I then brought her down towards me more and took her big breasts into my mouth and hands.
I realized I had not paid enough attention to them, especially since they were the reason I was in this situation to begin with! I’d even missed the opportunity to paint her tits with my cum after the blowjob but I will always choose a CIM from a woman!
Janie rode me to another orgasm but clearly was wiped out now by all of this. She was out of shape generally and out of shape sexually!
I hugged her tight again and swapped us one more time. With me back on top, I went hard in and out of Janie as my own cum was rising again finally.
Do I cum inside her or pull out? I wanted to cum on her tits but the idea of cumming inside my sister-in-law was also a strong pull for me.
Almost on cue, Janie locked her legs around my ass and told me to finish inside her.
“Don’t even dare think about pulling out of me” were her exact words!
And with that, I fired my second load of the night with Janie, this time inside her 50+ year old pussy. She wrapped her arms around me as I continued pumping into her. I fully collapsed onto her while still slowly moving in and out of her.
She just kept whispering to me “Thank you, thank you, thank you.”
She told me it had been nearly two years since Lenny had fucked her and even then he had not been able to keep it up and cum in her. I then learned that my sister-in-law has a cum fetish, especially it being fired into her, whether down her throat or inside her pussy. We had checked both off and she purred, satisfied for the first time in years.
It was a good start to the long weekend at the cabin…