Our First Anal Adventure

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Our First Anal AdventureZee had very conflicted feelings about anal sex. The first time I asked her if she was into it, she replied “That part of me is an exit. Just an exit.” I thought that was the end of it.Every so often, though, she’d bring it up. Usually it was in relation to her part-time job as a cam model. I didn’t tell you that? Well, don’t judge me, OK? There were always members asking her to do anal. I don’t blame them for asking, either.I always said that Zee’s ass was perfect for doggy style. It was also perfect for anal. Big, round, firm, smooth. A butt that complemented her curves wonderfully. I could see why guys would want to fuck her in the ass or watch her fuck herself there.But Zee always refused. I learned why about a year after we started seeing each other online. It seems she had a boyfriend a few years before she met me. The guy tried to do her anally one night, gonzo porn star style. Hard, fast, no lube, and he wouldn’t stop when she begged him to stop. Even though he didn’t get his cock very far up Zee’s ass, it caused her a lot of pain. And it turned her off anal. I’m surprised she didn’t castrate him for that.When Zee told me that, I understood why she was so reluctant to give it another go. And I told her that if she ever wanted to try anal with me I’d be gentle, take my time, and stop the moment it started to hurt her. It turns out that she remembered me saying that.How do I know? About two and a half months into my stay in Manila, we were at my place one evening. Sitting on the sofa, cuddling, just enjoying each other’s company. Zee looked up at me and said “Dan, I want you to fuck me in the ass.”Needless to say I was surprised. Shocked actually. “What about that part of you being only an exit?” I asked.Zee looked me right in the eye. “I’ve been curious about anal for a long time, and I remember what you said about being gentle. And I love and trust you enough to take me up there.”I put a hand gently on one of her cheeks and gave her a deep kiss. “OK, love,” I said, “If we’re going to do this we’re going to take it slowly. I want this to feel good for you.”I told Zee to meet me in the bedroom. I went into the bathroom küçükçekmece escort to find something slippery. I didn’t have any real lube (I made a note to pick that up the next day), but I did have a bottle of baby oil. I grabbed that and a couple of towels, and headed into my bedroom.She’d almost finished getting undressed when I stepped through the door. I took a second to take in my lady’s sexy curves (I loved looking at and running my hands over those curves), then instructed her to get on the bed on all fours while I stripped down.I put three pillows topped with a towel under her belly, which positioned Zee’s big beautiful butt up in the air. I could have looked at that sight all day …I gave each of Zee’s ass cheeks a kiss. She let out a little giggle and wiggled her butt as she always did whenever I did that. I warmed up some baby oil in my hands and then gently massaged it into her ass. I could feel her butt muscles relax under my oily hands while Zee let out little contented sighs and moans.I did that for a few minutes until she was relaxed enough for what I had planned next. “Reach back and start playing with your clit,” I told her.Two of the fingers on her right hand slowly started rubbing her pussy. “Stay relaxed,” I told her while I gently spread her ass cheeks and dribbled a bit of oil on her little asshole. The index finger of my right hand slowly slipped between those lovely cheeks and gently touched her puckered hole.Zee tensed up a bit. I whispered in her ear “Don’t worry. Nothing’s going in right now. Just relax and enjoy the feeling.”She relaxed and kept rubbing her pussy while the tip of my finger traced light little circles around her asshole. At the same time, I gently kissed Zee’s neck and shoulders. All I wanted to do was get her associating pleasure with that part of her body.And it seemed to be working. The combination of her fingers, mine, and my kisses brought deeper moans and sighs from inside her. While this was happening, I’d gotten harder than I’d been in a while, and precum was really dripping from the tip of my cock.After küçükyalı escort a couple of more minutes, I couldn’t take it anymore. I positioned myself behind her and slipped my cock into Zee’s wet pussy. We made love doggy style while I gently rubbed her asshole with my oiled thumb. We both came quickly, with simultaneous gasps.I pulled out, rolled Zee over, lay on top of her with my head pillowed on her large breasts. Between pants she told me how amazing that felt. I couldn’t disagree. Then Zee asked “What’s next?””Do you want some more?” I asked. She nodded, with a smile and a greedy look in her eyes.”Let’s take a rest and if you’re ready, we’ll go to the next step.”That came a few minutes later. I got Zee back into position, oiled up her ass and my hand again, and asked her to start rubbing herself.As she did that, I told her I was going to slide a finger into her ass. “If it hurts,” I said, “Let me know and I’ll stop.”Zee didn’t flinch or tense up this time. My middle finger gently circled her asshole again for a few moments, then I slowly began to slip it into Zee’s ass. She was so relaxed that I could slide my finger all the way in, working the baby oil into her anus.As I slowly and gently fingered her ass, I told Zee keep rubbing her pussy. She did, and started to moan louder. One of her fingers then two slipped in and out of her pussy, as mine slid in and out of her other hole.It only took a couple of more minutes for Zee to cum again, her anus clamping down on my finger. I held her close for a few moments and after we got cleaned up, we held each other in bed.”I never thought taking anything in my ass would feel that good,” she told me. “Thank you for that,” she said and then gave me a deep kiss.”When can we do it for real?” she asked.”Do you think you’re ready to have my cock in that big, beautiful butt of yours?” I asked. Zee nodded. “I know you won’t hurt me,” she said.”How about tomorrow, then? I need to pick up some good lubricant at the pharmacy. Baby oil doesn’t cut it when doing anal.”Zee didn’t say anything, just held me close. We both kültür escort fell asleep in each other’s arms.The next morning, a Saturday, I woke up and Zee wasn’t beside me. I couldn’t hear her in my apartment. I started wondering if I’d gone a bit too far last night and that she’d gotten cold feet. As I was mentally kicking myself, I heard the door of the apartment open and then close.Zee walked into the bedroom and, with a sexy but slightly wicked smile, held out a little plastic bottle. She’d gone to the pharmacy across the street and picked up some lube.She quickly slipped out of her clothes, had me lie back, and started sucking my cock. Her lips and tongue, both soft and moist, did their job and I was hard before I knew it. Zee squeezed some lube into the palm of her hand and slowly worked it into my hard shaft.As we did the night before, I propped Zee up with pillows under her belly. I squeezed a dollop of lube out of the bottle and slowly, gently worked it into her ass with a finger. Zee moaned gently as I did that. I knew she was ready.Getting Zee to spread her cheeks, I positioned my cock on her rosebud and slowly, gently started working it in. Inch by inch my cock disappeared into my love’s ass. The lube helped, but it was still a bit of a tight squeeze. I managed to get all the way in. I held my cock there and kissed Zee’s ear, neck, and cheeks.”Fuck me. Fuck me now, please,” she said in a low, breathy voice.I did as I was told, slowly sliding my cock in and out of Zee’s ass. I tried to be as slow and deliberate gentle as possible. I wanted this experience to be good for both of us. We were both moaning with pleasure, then I thought I heard Zee start softly sobbing.Worried that I was hurting her, I asked “Do you want me to pull out?””No. Keep going,” she said. “It doesn’t hurt. It’s just so intense. It feels so nice.”I kept making gentle love to that amazing ass, trying to hold off cumming for as long as I could. It wasn’t easy. The feeling was intense for me, too. Far more intense than any other time I did anal in the past.It got to a point where I couldn’t hold out any longer and with a loud grunt I shot my load into Zee’s ass. “Oh, darling …” I heard her say as I came.I pulled my rapidly shrinking cock out, rolled Zee over, and held her close. She looked at me, a glow on her face and said “I came, too. I didn’t even touch my pussy.”We kissed, a deep and soft and wet kiss. “Thank you for sharing that experience with me, love,” I said.Zee and I held each other and enjoyed that warm feeling of having shared something wonderful.