I tried not to drool, but damn, having girls throw themselves at me like this was always a major turn-on. I didn’t feel like I was doing much, but what I did meant so much to these girls so they were willing to throw themselves naked at my feet, legs spread and fully available, and damn, for a guy who had just wanted to be faithful to Courtney, my girlfriend and future wife… I had more than twenty girls in my harem now!
“I’d be happy to, but there are a few things I’d like to discuss before we get too caught up in the moment,” I told her.
“I’m on the pill, so you don’t have to worry about condoms or pulling out.” She informed me. “And when it comes to breaking my hymen, it seemed like Cindy really hurt when it happened, so go slow and I’ll let you know when I’m ready for you to go again.”
“Did you bring lube for anal, or should we use mine?” I asked.
“… lube?” She asked.
“Yes, lube. Lubricant. Your vagina produces liquids that keep friction from making sex… unpleasant. Your ass doesn’t. So we have to use lube to make anal more pleasant.” I told her.
“… oh… they don’t usually…” she muttered.
“You watched porn for research?” I guessed.
She nodded.
“They usually cut out that part, but did you notice that their butts usually looked wet and shiny?” I asked.
She nodded again.
“That’s because they lubed it off-screen,” I explained.
“… oh… I’m glad you knew.” She whispered.
“Who knows? Everyone is different and I could believe that some people don’t need anal lube, but I wouldn’t plan on it. We can also try lubing up in your pussy then moving to your ass, but if that lube fades we can’t do it again without risk of yeast infections.” I told her. “But there are some lubes, especially silicone-based ones, like the one I have, that last for hours, so you could lube yourself up and stay that way and I could just slide into your prepared anus.”
Berkley seemed encouraged that her dream might be obtainable. “Anything else?”
“Is there anything you DON’T want me to do?” I asked her.
“Um, I was talking with some of the other girls and they said deepthroating is hard, so I don’t think I’ll go for that yet, but you can put your cock in and I’ll try to suck it. But I plan on working with you on figuring that out over a longer period of time.” She explained. “You see, I’m not sure yet if I’ll ever be one of the girls wanting to bear your children, but I do plan on being your executive housekeeper and acting head of staff for a long time, and having sex with you… well, it’s a really nice perk.”
“Okay. Gentle on the oral sex today. Anything else?” I asked.
Berkley thought, “Um… I don’t know. I’ll let you know if you go anywhere I don’t want you to, okay?”
“Sounds good.” And I leaned forward and kissed her.
Unsurprisingly, she was not a great kisser. I’d definitely have to teach her how to kiss. But the sloppy surprised kiss of an inexperienced virgin was almost guaranteed to get me hard.
I moved in, helping her out of her jacket while slowly educating Berkley on how to kiss. She cooperated but didn’t seem to know what to do, as I worked her buttons open, exposing her lacy white bra. Her clasp came undone easily and my mouth released her lips to suck on her virgin nipples.
Berkley moaned incoherently as my tongue circled her nipples, and I pulled her to me, lifting her and carrying her to the bed without releasing her nipple from my mouth. One hand began squeezing her other breast as I undid her pants with the other. I slowly worked her pants down until she kicked them off. Her matching lacy panties slipped off easily leaving her naked and ready to be fucked. I quickly shed my clothes and dove in to lick her pussy.
Berkley tried to speak as my tongue swirled on her clitoris, but words escaped her. She arched, pushing her pussy deeper into my face and my tongue caressed her hymen.
She reached down and pulled my head away from her. I sat back waiting for her to come down so she could speak.
“No…” she gasped. “I… want to feel it. Cindy said… that she could hardly feel you when you…. did it. I want to feel you make me a woman.”
“It may hurt. I usually do try to break your hymen while you are in an orgasm to minimize the pain.” I told her.
She shook her head. “If it hurts, I’ll bear with it. I want to feel it when I become a woman.”
“Okay.” I accepted.
She spread her legs and let me move into position. Her pussy was soaked. I had made her very aroused and I rubbed my solid cock up and down her slit.
“What are you doing?” She asked.
“I’m getting some of your natural lubricant on my cock so it goes in nice,” I told her.
She nodded and hitched her hips to try and make herself as available to me as possible.
I placed my now lubed head against her opening and slowly pushed it in, her womanhood opening to accept my rod. Her hymen caught the head of my penis, allowing no more than my tip to enter her. Berkley grabbed handfuls of the sheets.
“It’s best if you relax,” I told her.
She took a deep breath, released the sheets, and put her arms around my neck. I kissed her again, then asked her, “Are you ready?” She nodded and pulled me down for a kiss again.
I slowly began to push against her hymen, trying hard to make sure I didn’t lurch into her when it broke. Berkley whimpered into the kiss. Her hymen stretched, doing its best to keep me out of her depths, and then I felt it start to give. Breaking it quickly felt like bubble wrap popping in your fingers, and breaking it slowly, I could feel the initial give then the rest of the membrane tear.
Berkley put a hand on my chest, gently pushing me back.
“Are you okay?” I asked.
“Other than my pussy getting split open?” She asked through a grimace, “Yep. Just need a second.”
Her pussy juices and the blood of her virginity flowed around my throbbing cock. It felt so good, being just in her love tunnel. I could feel her pussy clenching and adjusting to the intrusion.
“Okay, try moving a little,” Berkley instructed.
I pulled back just a touch and then pushed back in. I kept gently rocking, not wanting to go further until she confirmed she was good.
Berkley sat up and looked at her pelvis, seeing the tiny fraction of my cock that was actually entering her.
“It goes deeper?” She gasped.
“Yep, are you ready to fit more inside you?” I asked.
“Yes, just… slowly and gently.” She instructed.
I kissed her and began caressing her breasts again, to approving moans, and slowly started opening her virgin pussy up. Thrust by thrust I buried my length into her, maybe a half inch deeper each thrust until I was hilt deep in her pussy. Her vagina was naturally deep enough to accept the whole length and potentially more if there was more dick to give, though I had no idea how much more she could handle. For all I knew another millimeter would bottom her out, but she could handle my entire length.
I began pinching her nipples lightly and thrusting slowly but deeply into her. Berkley moaned into the kiss, pulling me tight and accepting my gentle, but firm fucking. I slowly increased my pace, my thighs slapping against her ass.
Berkley broke the kiss, gasping for air and moaning, “Fuck me, Tom. I’m yours!”
I worked at a frenzied pace, plowing her hard and fast. She orgasmed and I latched onto her knack licking and sucking, not quite hard enough to leave a hickey and she responded enthusiastically. My climax rolled through my loins, and I released her neck.
“I’m going to fill you with my cum.” I told her, making Berkley shudder.
I pushed my cock as deep into her pussy as I could, and I couldn’t tell if I was just touching her cervix or if I managed to bottom out. My cock pulsed and my semen flooded her womb.
Berkley gasped, “Oh… Fuck…” She laid back feeling me fire the last sports of sperm into her newly opened pussy.
I was using every trick I knew to stay erect, and it wasn’t working. I pulled my softening cock from her spasming cunt. It looked so sexy and I almost forgot to ask her if she wanted to do the traditional post-first-fuck photo.
“Oh, um… sure.” Berkley conceded nervously.
I explained about the vaulting app we used and how secure it was.
“Oh, that’s good to know and I’ll be sure to let the staff know so they can prepare, mentally, for it.” She spread her legs and posed as I directed.
The picture was taken, and we cuddled.
“You’re still going to take my anal virginity too, right?” Berkley asked nervously.
“Yeah, I just need a few minutes for my dick to be ready to go again,” I told her.
“You mean it can’t just keep going?” Berkley asked, confused.
I explained about a guy’s refractory period and how I had techniques to try to ignore it, but they weren’t guaranteed to work.
“You could try giving me oral, or using your hand, but…” I referenced my blood, sperm, and pussy juice-covered cock.
Berkley conceded and we cuddled, me casually groping her tits and ass to keep her aroused as my cock recovered.
“So how many of the girls you’ve had in your harem have you done anal with?” Berkley asked.
“Well, Cindy and I hadn’t done anything before we came here, and Mary is a probationary member, so we haven’t really done anything.” I started.
“What’s up with that?” Berkley asked, confused as I twiddled her nipples.