In the midst of all the Boss Man craziness, Papa Bear and I took our vacation into the mountains. It was absolutely perfect. It was off season at the resort, so the place was pretty well deserted. We spent four days cooking, snuggling, drinking, wandering through town, swimming in the natural spring pools, and screwing.
One night, after coming in from the hot tub, we fell into bed naked. We kissed feverishly, drunkenly, and started groping and sucking and fucking. I was on my stomach and as he fucked me from behind, I half-purred, half-growled, “I want you to fuck my ass.”
This is something that has always been a challenge for us. It has something to do with how thick Papa Bear’s cock is, and how tight my ass is, but in the year and a half that we’ve been together, we have only achieved anal once, and I couldn’t take it for long.
This time, though, I guess I was just drunk enough, just horny enough, and just lubed enough.
He slid the head of his cock into me. I gasped, and told him to wait. He held still and I tried to relax. He slid in a little more. I whimpered and took a deep breath, somewhere in the space between pain and ecstasy. We continued like that for several minutes, me breathing and trying to relax, him waiting and then advancing. And then he was inside me.
I moaned loudly. “Fuck me,” I begged, and he did. I screamed. I screamed and moaned and swore, and told him how fucking good it felt. I begged for more–harder, faster. He pounded me while I came and came, and then he filled me with cum.
“Holy fucking shit.”
It was definitely worth the wait, but we both agreed that another year and a half is not allowed to pass before we do that again.
Being around Boss Man is pure hell. I feel like I’m in high school again. Part of me wants to fabricate excuses to talk to him, and part of me wants to avoid him at all costs. I haven’t had a legit crush like this in so long, and I have no idea how to handle it. Sixteen year old me just fantasized. About kissing. About sex. About him or her asking me out. About being a couple.
30 year old me does not have time for that. 30 year old me just wants to be done already. 30 year old me feels giddy sometimes, an anxious wreck sometimes, and like looking for another job immediately the rest of the time.
It’s fucking weird. Today, when our eyes met and he held my gaze and I knew what he was thinking, I felt incredibly sexy. Like even though we will likely never do anything, we have a secret: We want each other.
When I stabbed myself with a staple, he burst out laughing, and then said “Thank you for being you.” And I felt lit up from the inside.
Hours later, he licked his lips, and I visibly went weak in the knees. To the point where he said “Sorry,” and I refused to look at him for the rest of the day. I just want to die. I am so goddamn embarrassed. I want him so hard.
It was manageable before I drunk texted him a pic of myself in my underwear. But then the hot and heavy texting started, the fantasies, what we wanted to do to each other, and now…good goddamn. I literally can’t even.
We have talked about spending some time together in the next few weeks. I’m fucking terrified. If he is 100% sure that nothing can happen between us, I may not be able to be around him. I prefer not to humiliate myself further. Plus, he just started dating this chick off Tinder, after three months of celibacy, because he said I made him want sex again. Awesome.
I don’t think they’re exclusive (it’s been one date) but he tends to move fast. They could be a couple in a matter of days. Or maybe he’ll have lost interest by then, as he’s prone to do.
I don’t even know why I feel like this. He is just some guy. He is not poly or non- monogamous. He can be a dick. He is my SUPERVISOR. But while months ago you could cut the sexual tension with a knife, now it is literally suffocating.
This has bad idea written all over it. Someone save me from myself.
I fucked him. Good god, it was hot. That unmistakable, delicious energy you get when you’re sitting inches away from someone, looking into their turquoise eyes, talking coyly about anything at all, and you know they’re about to be inside you.
I love sizing them up. His huge hands made my breath catch in my throat. He had freckles on his tattooed arms. His hair was reddish brown, he was chewing gum, and I couldn’t help remembering the biceps from his photo.
He gave me a drink. I downed it in less than a minute. We laughed, and he asked me if I wanted another. I said yes. We went into the bedroom. We kissed. Groaned. Groped each other. He undressed me, pulling off his shirt, then mine. His pants, then mine. We kept kissing. He was a good kisser. Urgent and gentle and hot and surprising. He licked my neck and my nipple and between my legs. I gave him a hickey on his bicep, and sucked him until I swallowed his cum, then licked him clean.
He fingered me. I jolted and moaned. He laughed at how cute I am when I jump. We talked. Well, he talked–I listened. I do that. Draw people out, so I can get a sense of them, without giving anything away myself. Its why I should have been a therapist–everyone tells me that–if only I could get my own shit together. Get sane. Get stable.
I sucked him hard, and he slid his huge, veined, curved cock between my legs. I screamed as he entered me. I was dying for it. Panting. He pounded me HARD. Just like I needed him to. He moved me into different positions like a pretzel. He told me to get on my hands and knees and banged me from behind. He slid down on top of me and rubbed my insides with his dick, while playing with my clit. I screamed so hard I was surprised I had any voice left. He came in me. At least I’d been smart enough to use a condom.
We lay panting and sweaty, muttering curses under our breath. Hot. Horny. Half-crazy. He got me another drink, and I went to clean up. We cuddled. Stroked each other. Talked.
“We should go soon,” he said.
I wrapped my leg around his, not letting go.
“Let me up,” he said. “It will be worth it.”
I let him up.
He slid another condom over his enormous, throbbing cock, grabbed my leg, and pushed inside me.
I saw stars.
3 hours and change until Dark Daddy arrives at his hotel room and eventually summons me.
Body hair? Shaved and shaved again, just to make sure.
Lavender bath? Taken.
Clothing? Strewn all over my bed, with zero idea of what I am wearing.
Lingerie? Chosen, with a little help from the man himself (and he picked the retro set with polka dots–which is also my favourite–and which shocked the heck out of me since I was sure he would have picked something sluttier).
Hair? In progress.
DIY sugar/honey/coconut oil lip treatment? Completed.
Nerves? In check.
This past weekend Daddy set up a threesome for us. When we’d discussed it in the past, I told him I trusted him to pick out someone for us. When he showed me her picture, though, I have to admit I was turned off. She wasn’t my type at ALL, but Daddy thought she was yummy.
I didn’t know what the rules were. I kind of hinted at my hesitancy, but obviously wasn’t clear enough. I asked him about her personality–I thought I could tell what she’d be like from the photos she posted, but I was hoping I was wrong. When I hook up with someone from online, I don’t choose strictly on their looks. I pick someone who looks like my type of person (Daddy’s profile picture is a marathon photo, for instance), and if the person can banter, seems to be easy-going and like someone I think I’d enjoy hanging out with, then I move forward.
When I asked him about her messages though, he said she sounded “just fine.” Looking through some of her texts I had some misgivings, but I wasn’t sure how to broach it with him because he’d already made plans with her. I avoided commenting on her appearance (frankly, she looked over the top, loud and tacky), but gushed over the photos of another woman we are supposed to be hooking up with soon. I figured he’d pick up on the fact that I wasn’t so into this particular woman, but no dice.
The day before we were supposed to hook up I wasn’t feeling great. I texted Daddy that my stomach hurt, and he said that I needed to do whatever I could to feel better by Saturday because we are “meeting a new friend and need to make a good impression.” Right, then.
I was really nervous leading up to it, but was hoping that she would back out. Before she arrived at Daddy’s condo, he and I went out to dinner. He took me to this great restaurant that serves creole food and we had a really nice time. We talked a bit more about The Girlfriend and Yoga Girl, and all of our insecurities about the situation. I told him my fear that The Girlfriend may want me to be strictly for sex, and that she may not want him to care for me. He said that wasn’t up to her–she has to deal with the fact that he cares about me, and she has to deal with the fact that she cares about Yoga Girl, and if she doesn’t like it then obviously the two of them “are not forever.”
He took me home and we opened a bottle of wine while we waited for the other woman. We didn’t have sex because he wanted to make sure we were both horny as hell when she got there. I crossed my fingers that she would flake, but despite being late, she did show up.
She was even less my type in person than in her pictures. I tried not to let it show but I definitely would have never considered being with her in any other situation–you know when you’re not just not attracted, you’re actually UN-attracted? Yeah, that’s where I was.
So to force myself to be okay with the situation, I just kept drinking.
It was a bad situation all around.
We started fooling around on the couch, and eventually the three of us moved it to the bedroom. I licked her pussy and she licked mine. I licked and fingered her until she had a screaming orgasm, and then Daddy fucked me, and then fucked her from behind while she moaned and gasped and came again. After a long while he told her that he was not even close to coming, so she breathlessly asked if they could take a break.
She asked me if I had a cigarette, which I did. Daddy has me down to two a day and I’d already had my allotment for the day, but he allowed me to have another one with her out on the patio. Then I got on my knees outside and blew him. Blurred Lines came on the stereo and I started dancing with his cock still in my mouth, and then said “Wait, what happened, it’s over?” when the song ended. She burst out laughing and then I started giggling and then Daddy said if I was going to be laughing then that was the end of the blow job.
We went back inside and I pounded another glass of wine without permission.
Daddy was not impressed.
The other girl gave Daddy a blowjob of her own (a very impressive looking one, I might add!), while I got on my knees behind him and rimmed him.
“That’s a surprising development,” he said. He had asked me before whether I do that, but I’d told him it was a soft limit. Apparently all the alcohol did the trick because I did it with no issue and actually kind of liked it.
Annnd, everything after that is a blur.
Apparently there was more drinking of contraband wine, more smuggling of un-authorized cigarettes, much drunken stumbling about and many instances of disobedience and rudeness.
I told Daddy I loved him a bunch of times, even though I had promised myself I would wait to say it. At least he said it back.
I told him I wasn’t being loud, and then proceeded to scream, on purpose.
I bit Daddy’s ass hard–he later told me I was lucky he hadn’t responded by yanking me up by my hair and slapping me.
I wandered out onto the patio and tried to curl up and go to sleep under a towel.
I was so hammered that after the other girl left, Daddy put me to bed and set the alarm for two hours later. He said I was in no condition to get into a cab until I’d had some sleep. When he woke me up, I was still totally drunk, but in slightly better condition. He put me in a cab as I apologized profusely, and he just kept saying we’d talk about it in the morning.
He told me to text him when I got home safely, and by some miracle I managed to do that. He responded with “Sleep well, Baby Doll.” Swoon.
The next day we had a confusing and heated discussion via text.
He said I had acted like a drunken teenager.
I told him I only did that because he made it clear I was to fully participate and it was the only way I could make myself fuck someone I wasn’t remotely attracted to.
He said he’d had no idea I wasn’t attracted to her.
I asked him what he would like me to do next time instead, and he said “Not get hammered and act out? I expect better from you.”
I felt bereft. I felt sick all day and cried on and off. I went back and forth between being upset that I’d embarrassed and disappointed him, and feeling enraged that I’d been put in this situation in the first place. I texted him later and asked when he could talk. He said the next day (today). We squabbled a bit more and then, realizing that this conversation needed to be had in person in order for it to be at all productive, decided to leave it.
Tonight after work I went to Daddy’s condo. I was late because we were short staffed so I had to close. I texted Daddy that I would be there as soon as I could, and he responded with “sigh.”
I felt so nervous waiting for him to come to the door and let me in. I couldn’t look him in the eye and followed him back to his unit like a chastised puppy trailing behind its master.
Daddy shook his head. “Well, while we have this conversation you might as well be naked,” he said.
I obediently undressed and stood in the living room with my hands behind my back–a modified version of the submissive position.
“Bad Girl” by Madonna was playing. Despite my genuine heart-sickness over being in so much trouble, I had to stifle a giggle. It was clearly atmospheric. He made me stand there and listen to the entire song while he moved around in the kitchen.
When he came out he handed me a glass. I expected it to be just straight Coke–a message of some sort about how my drinking days were over–but to my surprise it had rum in it.
Daddy sat on the couch and I continued to stand. I held my drink in my hand and kept the other behind my back.
I stood there naked while he detailed my transgressions from Saturday night.
“It will never happen again,” he said when he was done. “What do you think is going to happen if you ever behave that way again?”
I shook my head. I couldn’t speak.
“You probably don’t want to know what is going to happen.”
“No, Sir, I don’t,” he said, but the message was crystal clear–I would lose him.
“Now,” he said. “You are not obligated to sleep with anyone if you don’t want to. Ideally, you would have told me you weren’t into her when I showed you her photo so I could have cancelled.”
“I tried to tell you Sir, but you made it clear I was expected to go through with it.”
“You didn’t tell me you weren’t into her–you just said you were nervous. You need to be more clear about that. Next time you choose the girl.”
“But what if we like their picture but we meet up and I can’t stand them?” I asked.
“Then we need a signal–say you have cramps or something.”
“Well,” he said. “At least there were a couple of good things to come out of Saturday night. One, we know you lick ass.”
“Two, it was very nice getting to cuddle with you for a couple of hours while you were passed out snoring like an asthmatic old man.”
The first thought I had when he kissed me was “WRONG. This is wrong.”
Logically speaking I know it’s fine for me to have sex with whoever I want to, but every so often slut-shaming and mono-normative thoughts creep into my head and it’s hard to shake them.
He led me inside and told me I needed to be wearing much less clothing, and the teenager inside me who was told she’d be forever sullied if she had sex with someone who was not her husband, quavered.
He started off by having me suck his cock, which didn’t help.
What would people say?
You shouldn’t be doing this.
Shut up, all of you.
We went into the bedroom where he immediately bent me over the bed. I was still swollen from the night before, so much so that despite being wet, he had a hard time entering me.
“I’m beginning to think you can’t handle me two nights in a row,” he said. “You’re so swollen its like fucking an 18 year old.”
Inside, I am still an 18 year old. Just now experimenting with my sexuality, because back then I was too scared and repressed to do so.
It hurt. I grit my teeth as he slammed into me. Told myself to relax like I do at the beginning of anal. Breathed. Whimpered. And eventually came.
It stopped hurting. I came again. I came so hard and got so tight that I pulled the condom right off him–he had to stop and put on another.
I came the way you should only be able to come from tantric sex–continually. I came for 20 minutes straight. As soon as one orgasm ended another began. I rose and crashed, whimpering, moaning, screaming and panting. Eventually, he came too, with me still in the middle of an endless orgasm.
He told me to get up on the bed for a cuddle but I could barely move. He kissed my neck and growled in my ear, sending more shivers of pleasure through me.
I am allowed.
I am allowed to feel this.
I am allowed to use my body in whatever way feels good.
I am allowed to orgasm, I am allowed to cuddle, I am allowed to suck cock, and I am allowed to do it with whoever I want as long as they want it, too.
My body, my life, my pleasure, my choice.
The only one who has to live with it is me.
I fucked him last night on my way home from work. At first my pussy was so swollen from the day before that I was worried I wouldn’t enjoy it, but within a minute or two I was screaming into a pillow. He does this thing…he tells me dirty stories in my ear. Weaves fantasies. Gets me off with both his words and his touch. I could write a collection of erotica with nothing but the scenarios he comes up with.
We fucked again tonight. The words “Daddy” and “Baby Girl” came out of both our mouths over and over. I didn’t even know he was a Dom, let alone a Daddy. I didn’t mention being a submissive on my AFF profile. Maybe we just recognized each other–out of over 100 men, I chose him.
Who am I kidding? I chose him because he wanted to meet for drinks instead of coffee.
I have a dom again–how do I keep unintentionally walking into this kind of relationship? He didn’t want me to be his submissive either–as a general rule he does not date the women he doms. But here we are anyway.
Fucking. Dating. Daddy/Baby girl.
That escalated quickly.