A MILF Family Friend and I During Medical Emergency

Last spring in 2025, a family member of ours had a medical emergency and ended up in the hospital. Had a pretty decent infection that thankfully was stopped before it got worse. My wife Megan and I rushed a few hours away from home to be with them during this time.

While the doctors thankfully got everything settled down in our family member Carol, she was going to spend a few nights in the hospital to make sure everything was fine. When we first walked in to see her, her best friend CJ was visiting her.

CJ is around 50, and has been Carol‘s friend for a long time. We had met her several times and always enjoyed her company.

The one thing about CJ is, she gives very long and deep hugs, to me at least. We also shared an affinity for a couple sports teams and she would often text me when they were playing or they were doing well.

CJ was married and had a teenage kid. She’s about 5’8”, normal mom bod with a normal size butt and decent size breasts. Her husband had a pretty boring day job, but then had a side gig that required him to travel on the weekends.

As we hung out in Carol’s hospital room, we chatted with CJ about what was going on with Carol plus her own life. She had been there for several hours before us and had already gotten the lay of the land so to speak.

I was hungry since we had left in such a hurry, and CJ was getting ready to leave, but revealed the cafeteria at the hospital wasn’t all that bad. Meg told me to go down with CJ and she can show you where the cafeteria is so you can get yourself something to eat.

So, CJ and I went downstairs. While it was clear cut where the cafeteria was, she still walked me to the entrance. We chatted for several minutes about this and that, then said our goodbyes with another one of her requisite deep hugs. With nobody else around, we held each other even longer than we normally did, and we both even had a little bit of massage on the other’s back for just a few seconds. I pulled back from her and purposely didn’t make eye contact as I was afraid I might kiss her.

She left and I went to get food, and then back up to Carol’s hospital room. Initially, we were supposed to stay at Carol’s house but decided we’d rather be closer so I got a hotel up the road. Meg was going to spend the night with her anyway, so I was gonna be by myself in the hotel. And as a seasoned traveler, I’d much rather be in a hotel room than someone’s house.

About 9:30, I excused myself to go check into the hotel and get some rest. By 10 o’clock I was up in my room and decided to send CJ a note, letting her know know about our new plans.

“Hey CJ, just an FYI, we decided to get a room at the Hilton up the road from the hospital. That way we’re much much closer than Carol’s house would’ve been. Meg is still spending the night with Carol, but this is our new plan. Really appreciate you being there today.“

Within moments, I got a reply from CJ saying how it was a great idea for me to get some rest. Before I can even reply to her reply, she added another line that said the day had been very stressful for her, and her husband had already left for his weekend gig, so did I want to grab a drink at the hotel? Her teenage son was fine staying by himself for a little bit.

Now, if you’ve ever read any of my stuff, you know I’m not some naïve, innocent boy that doesn’t pick up on signals. It was clear CJ and I had an attraction to each other, but she was a very good friend of Carol’s, and I wasn’t sure if I wanted to risk opening up that door.

But I sent my reply to CJ saying the more the merrier, come on over. I had actually already gotten into my sleeping shorts and tee when I sent her the original text, so I quickly got redressed and went downstairs to the lobby. It was a Thursday night, but the bar was hopping so I sauntered over to the hotel sundry shop. Sure enough they had what I needed – Travel size boxes of condoms and alcohol.

I grabbed a couple two-packs along with a bottle of wine to take back up to the room. I paid the front desk with cash, and then walked over to the bar and grabbed two wine glasses from them. I went back up to the room, got everything ready and went back to meet CJ down in the lobby as she arrived.

She walked into the large atrium lobby and looked great. She’d obviously done her hair up and added some makeup and lipstick since the hospital while still keeping casual clothes on. Just like before we gave each other an extra long hug and this time I made eye contact with her to try to get a read on the situation. Her eyes and smiles told me everything I needed to know.

I told her the bar seemed awfully loud right now, and I had brought wine, would she like to go upstairs. I made sure I didn’t use the words “my room”or “the room”, but obviously upstairs meant exactly that.

I was confirmed in my belief when she didn’t hesitate in saying yes to come up. Within a few minutes we were at the door and walked into my room.

I gently closed the door behind me and watched her walk deeper into the room and closer to the bed. She turned around, looked at me and smiled very sexy.

“Can I get you some wine,“ I asked her. “Or would you prefer we save that for later?“

She chuckled and we both closed the gap between us and took each other in our arms like we had many times for innocent hugs, except this time we kissed. And we kissed passionately. Our tongues danced, and we moaned our appreciation of this years long desire being finally fulfilled.

I thought about being with CJ over the years, but this had ramped up pretty quickly in the last few hours. Maybe it was the emotional stress from Carol being in the hospital, but we were both primed and ready. I had jeans and a golf hoodie on. She had a light sweater and jeans.

My hands immediately went up under her sweater and found her midsize breasts encased in her bra. I wasted no time in sliding my hands under the bottom of the bra and lifting it to find her hard nipples ready for my touch.

As I fondled her, CJ took her sweater off and then unhooked her bra to give me full access to her breasts. She had a little pooch left over from being pregnant back in the day but looked great! I leaned back and took in her full top frontal nudity and smiled in appreciation of how she looked.

I took advantage of the free access and leaned down to take one of her nipples into my mouth and started sucking and licking on it. I took her other breast and massaged it with my hand, tweaking that nipple.

She held my head down on her breasts and then moved her hands down to my ass. She then went around front and started massaging my fully hard cock, which was straining against my jeans.

She unbuckled my belt and loosen my jeans and pull down the zipper. They stayed around my hips as my hard on was keeping them up. CJ then pulled my golf hoodie and undershirt off in one fell swoop. She leaned down and kissed my chest before returning her attention to my cock with her hand.

We kept kissing now as we both groped the other, and I pulled down her jeans. She wiggled out of them and now stood in only her panties. I gently moved us over towards the hotel desk and had her sit on the edge. I sat down in the rolling chair and spread her legs as she sat there.

I recalled a time a few years back when CJ, Meg, Carol and I had some drinks and the tongues were loosened. During this, CJ confessed that her husband did not like giving oral and didn’t do it to her, despite her pleas. I remember thinking (but NOT saying) perhaps we should trade spouses because Meg also did not like oral while I did.

So now I had CJ’s pussy, covered by standard black panties, mere inches from my face and tongue. I honestly don’t know if I am good at oral but I can make most woman cum that way, and anything is better than what CJ’s husband normally gave her – which was nothing!

I pulled her panties to the side and leaned in. I immediately felt her wetness from the excitement thus far and that got me going even more. I licked her pussy lips and dove in. She had butterfly lips, which always are great as a woman’s wetness gathers on them as she gets excited. While I held her panties to the side with one hand, I took my other hand and gently penetrated her with my index and middle finger. I didn’t go far at first but started doubling the effort between my tongue and my fingers.

She grabbed my head and pulled me tighter to her. Another good sign. Her moans got louder and longer. She was definitely rising towards a good cum. Just as she seemingly was close, I stopped. She whimpered but I wanted full access to her pussy.

So I pulled her panties down and out of the way. She kicked them off to the side and I dove back into her. I pulled her even closer to the edge of the desk by grabbing her ass and sliding her towards me. She spread her legs fully and then propped them up over my shoulders.

She quickly found her pace again and within a minute of losing her panties, she was now cumming for the first time tonight. She bit her lip and suppressed much of it but she was definitely hitting an orgasm. She would later tell me she was being shy, both with me and since we were at a hotel. I get not wanting to wake the neighbors but a it’s a little late to be shy with me!

I licked up her flowing juices and kissed her pussy. I then stood up and kissed her. She was again a little shy with that as obviously her husband, who never ate her out to begin with, would not have then kissed her so she could taste herself on his tongue. After a moment or two of hesitation and with my encouragement, she leaned into the kiss with me and opened her mouth to my tongue.

I grabbed her ass again and pulled even more on the edge of the desk but my body was now there to hold her in place. I still had my jeans on but my hard cock was pressing up against her bare pussy. I started rubbing myself on her, and humping. We both moaned as we kissed, knowing this was the ultimate goal – my cock inside of her.

I stood her up and swapped places with her. I sat her down in the desk chair and pulled my pants and boxers down. I kicked them away and now stood fully naked in front of her, with my dick at the perfect height as she sat.

Now, I’d never heard her talk about whether she liked to give blowjobs and it can be awkward with a new lover. But I learned long ago that you need to set the expectation on day one of oral sex or you may never get it without begging (I had failed with Meg so long ago!).

She looked up at me as I presented my hard cock. She smiled and took me in her hand and started slowly jerking me off. She licked my tip but never went past her lips with it. She did this for about a minute and I realized this was the extent she was initially prepared to do. It’s probably what she occasionally (birthday, anniversary) did for her husband but it wasn’t good enough for me. If you’re going to cheat, do things you haven’t done before.

So I took CJ’s hand off my cock and told her to only use her mouth and tongue. I told her to play with her pussy and tits as she truly sucked me. I told her to take me halfway, 3.5 inches of my 7. Use her tongue and her lips to work my cock.

She looked a little unsure but I kept encouraging her and enjoyed the show as she bit by bit got more brave and better at sucking me off. And within a few minutes, while she wasn’t ready for porn, she was doing a good job. She was very coachable and started to get into it, especially as I encouraged and complimented her. My moans certainly helped!

Before long, she had me going good. I took the back of her head and held on. I now started to face fuck her, still keeping only half or so of my cock in her mouth. But her lips and tongue were creating a nice pussy like affect on me. And the site of her doing this pushed me over the edge.

I had not started this with the intention of cumming down her throat, as I always worry they could change their mind about me fucking them once I’ve cum.

But she felt too good and I was too far gone at this point. I began to warn her what was coming when she went deeper on me. 4 inches, then 5. She tried to go deeper and gagged herself but had found a good rhythm on my cock.

“CJ, I’m going to…”

And with that, she reached around grabbed my ass with both hands and pulled me further into her mouth and down her throat. This really gagged her but she took it. And I was done for!

I fired shot after shot of cum down her throat. She gagged a bit but still swallowed the first three pulses and then backed me out of her mouth. The fourth shot hit her in the lips and the fifth her cheek. I took hold of my cock and jerked off the rest onto her MILF tits.

Once she got her breath back, she gleefully squealed at what had just happened. She took my cock back into her mouth and cleaned me off. She then wiped the cum off her cheeks and lips and swallowed that as well. She rubbed in the small amount on her breasts and then licked her fingers clean.

“That was very hot CJ. I wasn’t quite sure you were up for that but you sucked me dry!”

“Mmmm, not my normal deal at home but I wanted to do something different tonight! I kind of got into a groove there at the end! It’s been a long time since I tasted cum.”

I pulled her up out of the chair and kissed her. She leaned into the kiss, as she knew I was tasting myself on her tongue while she was getting a taste of her pussy again as well. I massaged her breasts again – I really liked them! They had a standard 50 year old, mommy sag to them but still were relatively firm. Her nipples responded to my touch and were very hard.

I had softened slightly after my orgasm but this new make-out session got me going full staff again. We swapped positions again and I took the chair back. I grabbed my hotel sundry shop condom purchase and pulled one out. I opened the foil wrapper and slid the condom on, with a little effort given I had dried cum and spit on there from her blowjob. And because I stink at putting condoms on!

CJ meanwhile watched me do this intently while playing with her pussy. Once I had the condom on, I went back to her and licked her pussy. She was flowing from her own touch and I got another great taste of her.

I leaned back in the chair and held my cock for her. I slid forward in the chair and she maneuvered over me. Her pussy lips met my head and slowly enveloped it. I normally like to make eye contact but I was mesmerized by the sight of me disappearing into CJ’s inner folds. This was so naughty, and certainly not something on my mind as I raced across the state mere hours earlier.

I held CJ’s hips as she finished sliding down onto me. Her body weight was now fully on me as she positioned herself with her knees on the seat with me. She grabbed the back of the chair and started moving up and down on me. We kissed again. She was a very good kisser and I was enjoying that part as well.

Now fully inside of her, she really started to ride me. I massaged her breasts and sucked her nipples. She was moaning her appreciation of my cock and my touch on her breasts. I looked down again at our crotches working in rhythm. She felt wonderful.

I started talking to her now. Her husband clearly didn’t do much with her in bed and I was going to push her to some new limits.

“Fuck me CJ. Fuck me like you always wanted. How long have you wanted my cock inside you? Hmmm?”

“Oh my god Ken, you feel so good in me. I’ve wanted this from the first time I met you. It was the first time I’d ever really thought about cheating on my husband.”

“So, am I your first?”

She nodded shyly and then continued.

“This feels amazing and I’m sorry we haven’t done this before now. You are really good at this. I’m doing things I’ve never done.”

I think she knew now as I fucked her and took control of the situation that she wasn’t my first cheat. Why even ask me? Why make me lie? And she liked that I was thoroughly fucking her for perhaps the first time in her life.

With her admissions, I found another gear, grabbed her hips and really fucked up into her as she rode me. When she came down on me, I was pumping up into her. Our bodies were slamming into each other now and she was rising to another orgasm.

She let out a pleasure scream and took me back into her mouth, as she self muted herself! Her tongue danced in my mouth as she rode out her orgasm on my cock.

Given I had just cum a few minutes earlier in her mouth, I had plenty of stamina so I really started pumping up into her once she regained her breath. I held her ass with one hand and took my thumb to rub her clit as she continued riding me.

This immediately got her on the path back to cumming and she let me know by saying “yes” over and over. I told her to take my place at her clit and play with herself. It is lovely when a woman does this.

With her playing with her love button, and my cock driving in and out of her, she quickly rose again. She buried her face into my shoulder as she rode me to another orgasm.

She’d had two orgasms riding me but now it was my turn. I grabbed underneath her ass, braced my legs and lifted the both of us out of the chair . She squealed with glee and laughed at the sudden change. I carried her back to the desk edge and sat her down, my cock never losing contact with her pussy.

I looked down at my condom covered cock as I moved in and out of her. CJ also looked down at our privates moving in sync and moaned again at the thought of what we were doing.

I really increased the pace at this thought. I was finally inside her and was getting close. I’d already cum down her throat but my second orgasm was fast approaching. I kept looking down at my cock and CJ’s pussy.

“You want to finish in me don’t you? You want to take the condom off and put it back into me, bare?”

Fuck yes, I wanted to do that but that seemed a bit risky. I’m tested and she claimed she’d never cheated before but what about her husband. He travels so who knows…

“I do, I do. I want to so badly CJ but…”

She put her finger over my lips and looked at me before saying:

“Gary (her husband) hasn’t been inside of me without a condom in over ten years. It was back when we trying for a second.”

I really started pumping into her hard now. This talk had me going! If she was serious about letting me cum in her, I needed to watch my pace or I’d quickly hit the point of no return still all wrapped up.

“I want you to leave me something tonight, to have in me when I go home. I can’t stay all night but this way I’ve still got you with me. Cum in me honey.”

It was bad, roll your eyes dialogue if this was made up but super hot as she said it. I gave it a moments thought, along with the idea she might still be fertile. Fuck it!

I pulled out and rolled the condom off my cock. I started to go hard back into her as I was so fired up and almost at my peak but I remembered my cock had no lube on it now. So, I put two fingers into CJ’s pussy and got some natural lube to put on my tip.

I placed myself back at her entrance and pushed back in. 2-3 inches easy, then more resistance. But much more quickly than before, I was fully in her within a few moments. Obviously she felt even better now that I was raw. I could feel her pussy walls on my cock. Tightening back around me as I picked up the pace. Gripping me just enough.

I looked down again at my cock entering her pussy and smiled, now with no barriers between us. We made eye contact again and kissed. Then she closed her eyes and really started bucking against my cock. Obviously she felt phenomenal to me and she felt the same about me in her.

She had been holding herself up on the desk but switched up to wrap her arms around my neck. She wrapped her legs around my back and ass. She was now hanging onto me to the point her ass lifted up off the desk and I was holding her up. I moved my hands underneath her ass and took some of the weight off my neck and back. I’d already lifted her up out of the chair, so she was within my range no doubt.

As I kept pumping into CJ’s pussy, I fully scooped her up and swung around to the bed. I had actually planned on not using the bed as I didn’t want to risk leaving any mess there since Meg would eventually be in here. But I needed her on the bed. I wanted to be fully on top of her body and drive down into her.

Together as one, still joined at her pussy and my hands underneath ass, as well as her arms around my neck and legs around my ass, we fell to the much softer bed. When I first arrived to the room, I had pulled the covers back in anticipation of just myself going to bed.

Now, just in that short time since, I was pumping in and out of CJ, a woman I had long admired but never really gave serious thought to fucking because of who she knew. We had not even discussed this needing to be a secret but she had a lot to lose as well.

We had now crossed that line and were way beyond it. Not only was I inside her pussy, I had slipped off the condom and was fully raw. In telling me to take off the condom, she’d also told me to cum in her…to leave her a present to take home with her, and in her.

As that went thru my mind, I started really driving into her. The mattress cushioned us now but even it was getting a bit stressed with our fucking. The bed creaked and even moved a bit but its moorings kept in place.

Our lips came together and her kisses and tongue on mine was the final straw.

“CJ, CJ, CJ…” I squeaked out in a strained voice. I was cumming. I was cumming in her.

I still didn’t believe this was happening and the crazy excitement of it all, now combined with a strong orgasm, I was actually felt lightheaded. But I kept pounding into CJ and she kept begging me for more.

“Give it all to me. Please. Yes yes yes!”

And with that, CJ with a little help from me and my cock, had talked herself into another orgasm of her own. She locked arms and legs around me and we stayed deeply connected. There was stupidity to all of this, including cumming in her, but this was so hot and exciting.

I buried my head into her shoulder and then moved down to her breasts, kissing them as I regained my breath and tried not to pass out.

I had seen stars as I came. It had been a stressful day for both of us and we had just relieved each other once again. My hips were slowly grinding into CJ but we were done. Exhausted. The day had worn on us and while we felt energized together, we now hit the post coital cliff dive!

I could have fallen asleep on top of her, while still in her! But I did pull out of her and gave her a long kiss. Sometimes when spur of the moment sex happens, the awkwardness can pop up immediately. We’d both cheated on our spouses, her for the first time. Kissing and maintaining contact helps with the transition.

She welcomed my kissing and we made out a bit. She giggled that we were laying here naked, having fucked each other’s brains out. I took another step and talked about it. I held her hand and looked her in the eye.

“How are you doing?”

“I’m great. I wanted this. As scary as Carol’s situation was, when I heard you were coming I got butterflies all over again. I drove over here knowing I was going to sleep with you…well, no sleeping and we barely touched the bed!”

I laughed at her comment, squeezed her hand and kissed her again. Her pussy was filled with my cum and she was leaking a bit back onto the sheets. I’d need to call housekeeping to get those changed but that was for later. I fingered her messy lips, tickling her clit. She started to ride my hand before stopping.

“I need to go and if you do that any more, I might not go home.”

I didn’t actually want her to go home but we kissed again and she got dressed. I offered to walk her down but she said it was already a bit dangerous that we came up here together. She only lived three miles away and while it was a hotel bar, you just never know!

As she dressed, she saw the extra condoms and laughed. Two two packs equaled four condoms.

“Four times, huh?” God I wish I could stay and get another three times in tonight. Keep those handy my dear.”

I agreed and said I couldn’t wait. Of course, I had just finished inside of her so why would I go back to condoms now??! Those were going in the trash downstairs right away!

We kissed again and she headed out. We weren’t done for the weekend but we both needed our rest now.

(I have to admit, I woke up at 5am and jerked off thinking about having been with CJ. It was so surreal to me!)