My girlfriend Lisa was quite literally the woman of my dreams. She was sexy and always ready to go with everything that I proposed. She was adventurous and we had the best time together and I felt that she was the one.
She was one of the most attractive women I ever saw, starting with her long red hair and long legs and ending with her perky breasts and beautiful, tight ass. It was actually the part of her body that I loved the most. I loved looking at her butt, touching it, and kissing it whenever we were naked in bed.
Lisa allowed me more than enough things in bed and I was happy with it. It was rare to meet a woman like her, who genuinely loved and enjoyed all kinds of sex. Of course, me being obsessed with her ass, I wanted to try that hole too and Lisa was ready for it too, but there was a problem. I know, it sounds as if I’m bragging, but my dick is pretty big. We were even having problems with Lisa taking me in her pussy, even though she got used to my size. I couldn’t imagine what it would take for her to have anal with me. Still, she was pretty eager and wanted it.
We were talking about it from time to time, but I was never pushing Lisa to try. I appreciated just having her around and knowing that she wanted to make me happy in any way I wanted it. I didn’t expect her to do something about it, but one night it changed.
I could see that Lisa was planning something for a few days. She was smiling at me and being playful and I wanted to know what it was. She told me I will find out soon and I was excited at that moment.
One night I came home late after work, expecting Lisa to already be asleep when I came, but when I opened the door, I saw the living room dimly lit. Lisa wasn’t there, but I followed the sounds of the slow music that I heard from the bedroom. Lisa was there, laying on the bed, wearing sexy lingerie and waiting for me.
“Do you like your surprise?” she asked, getting up and coming closer to me. I couldn’t take my eyes away from her body, my cock instantly getting hard.
“Yes, very much,” I said, smiling.
I pulled Lisa close, kissing her hard and getting her off the floor. I walked to the bed, gently putting her there, laying on top of her, and feeling the heat of her body. Lisa put her hand on the front of my pants and I felt her squeezing me through the fabric.
“Wait a moment, I need to show you the surprise I prepared,” she smiled. I moved away, letting her get on the fours and turn her back to me.
Lisa was wearing a lacy thong and I could see the base of a big butt plug in her asshole. I lost my breath, knowing what it meant. She wanted me to fuck her in the ass and was preparing for it. She moved her ass, inviting me and I smiled.
“Are you sure that you’re ready for it?” I asked, putting my hands on her ass and squeezing her.
“Yes,” Lisa smiled, turning to me and smiling. “I’m ready to give you my anal virginity”
I couldn’t get any harder than I was right now. I wanted it badly, but I knew that I needed to make sure that Lisa could really go through with it. I took my clothes off, looking at where the butt plug was and already imagining my cock there.
When I was ready, I took Lisa’s panties off her and started gently pulling the butt plug off. Lisa was moaning lightly as I did it, putting her hands on her ass and spreading it, looking even sexier now.
Her asshole didn’t look as tight as it had before and it was definitely for the best. Lisa prepared lube for me to use and I put some on my cock, before I put it to her asshole. My tip looked huge against it and I just hoped that Lisa would like it.
I pushed inside her slowly, hearing Lisa whimper and moan. I was asking her all the time if everything was okay and she was telling me to just keep going. I did, watching as her asshole slowly took my whole tip in, but at that moment everything stopped.
It felt so great to be inside her, she was so tight and amazing, but I couldn’t move another inch in. I was so afraid of hurting her, that I was stuck with only my tip inside her.
“Give me more, I can take it!” Lisa insisted.
“No, that’s enough. I don’t want to push it”
I kept pushing my tip in and out, enjoying the tightness of her asshole, and soon, with even that, I came inside her. My cum leaked out of her ass as soon as I pulled out.
“It was amazing,” I said, kissing Lisa’s shoulder.
I went to the bathroom, to wash myself and when I came back Lisa was sitting on the bed, looking upset.
‘I’m sorry,” she said, looking at me. “I wanted it to be amazing, but…”
“It was amazing,” I said, sitting close to her. “I’m so grateful for it. We can try another time”
I kissed her until Lisa smiled at me and I saw a fire in her eyes once again.
“Well, I know a hole where I can take you fully,” she smiled, getting on her knees in front of me.
“Get ready for an amazing night”
Lisa was quick to take my cock in her mouth. I knew that she could do it well, so I watched her open her mouth wide and take my cock slowly until every inch was inside her. I groaned, enjoying how tight her mouth and throat were around me. It felt amazing and so good, like everything Lisa did.
She looked at me, and I saw her taking all my length inside her. Her mouth was so wide open and her lips were puffed, I loved to see it. She moved away, now taking my balls in and sucking lightly. It felt so good I was almost ready to cum again, but I knew that I needed to make Lisa feel good too for everything that she did for me.
“Get here,” I said, putting her on the bed. Lisa laughed, spreading her legs for me.
Her pussy was wet and amazing and I loved seeing her taking my tip inside. She felt tight around me, not as tight as her ass, but I still enjoyed it. Lisa moaned, loving it, while I pushed deeper inside her. I loved watching her pretty pink pussy taking me in so deep, it was such a beautiful and sexy picture. She was wet enough to make it feel easy and every moment I was pounding inside her harder and harder.
“Yes, use my pussy, cum inside me!” Lisa moaned out, pulling me close.
I was even deeper inside her, slamming my hips against hers until I felt her pussy go tight. She sobbed, her orgasm hitting her before I finished inside her. Now all of her holes were used and fucked by me.
“Thank you for the night,” I said, kissing her. I was grateful that she gave me a chance to fuck her like that and I couldn’t wait to get another chance to do it.