Rose started speaking again, her eyes on me, “That was so beautiful sweetie. Thank you for sharing this with me. You are so passionate and lovely. I will never forget this beautiful night.” She rubbed her hands on Sierra’s back and petted her hair.
I really slowed it down now, thinking maybe Sierra needed to rest, she seemed really wiped out. I slowly pulled out all the way for a second when Sierra spoke in a weak voice, “Danny?”
“Mmmhmm,” I said as I rubbed her upturned cheeks with my hands.
“Were you really planning to slide that giant cock of yours in my ass?”
Uh, was I? I was caught off guard. I guess it did seem like a perfect opportunity before us, with Sierra lying there in her loving mother’s arms, softly cradled in her bosom.
“Anything baby,” I said as I rubbed my fingers along Sierra’s damp pussy and then began to rub around her puckered little anus.
I gently pushed my fingertip into her exposed flower and let it out again slowly. Sierra breathed out a heavy sigh, and I could sense this was feeling good.
I rubbed her other smooth cheek while I pressed into her again. I kept it in for longer this time, gently pulling back without withdrawing, then pushing in more deeply. Sierra breathed out heavily and looked back at me over her shoulder from her mother’s embrace. “That’s it baby.”
With this encouragement I pushed in a bit deeper and started pumping my finger in and out, watching for signs of discomfort. I curled my embedded finger around and pulled it side to side, stretching her constricting muscle a bit, and then pumping in and out some more.
“Oh that’s nice Daniel,” she said as Rose continued to stroke her back and soft hair. I pulled and stretched with my one finger, and then tried to press another fingertip in beside it.
“Oh,” Sierra chirped, “that’s going to take a minute.” So I froze with one finger buried and another with just the tip inside while she relaxed. I realized that to fit my whole cock in there, we would need some fresh lubrication, so I softly moved my hard cock back into her pussy.
“Oh god,” was all she could get out, and I could tell that the sex was at least helping to distract her from the anal discomfort. I slowly slid my cock in and out, and used the movement to help mask the insistent pushing at her back door, in and out of her pussy, deeper and deeper inside her delicate tush.
Very soon there was a noticeable relaxing of her muscle, and my second finger was quickly well inside, joining the first in the darkness of her forbidden entrance.
I cautiously pressed my digits into her backside, further and further as we slowly continued to fuck. The way she started to move let me know that we were getting there, and my fingers were easily plunging in and out of her hole as we started to pick up a bit of steam.
I looked up and noticed Rose watching my fingers work their way into her daughter’s tight backside, my gaze having been mainly focused on my task at hand. It was starting to get hot again, and my cock was smoothly gliding into and out of my girlfriend’s moist pussy. I gazed into Rose’s eyes and she smiled and rubbed her daughters soft skin some more.
I was just starting to debate whether or not I would attempt to work another finger into her ass, when Sierra stopped moving. “Danny, I think I’m ready to feel your cock in there now.”
Okay.
I pulled out and slowly dislodged my fingers. Sierra brought her hips down a little to help me gain entrance. I simply placed the head of my cock up against her without pushing, and rubbed it in very small circles as we held otherwise still.
I could sense Sierra’s urgency as she leaned back into my cock, pushing the head up against her closed door. I grabbed onto my shaft and gently pushed back, keeping an even amount of pressure back there for her ass to respond to. We both kept the pressure on, and after about half a minute I could feel the gates crack open a bit.
“Oh god,” Sierra moaned, her legs starting to tremble.
“That’s it honey,” Rose began in a comforting tone, “just relax and let him in. It’s okay. You’re doing great, just push back a little and let him in sweetie. That’s it.”
As Rose softly cooed to her little girl, I could see the head of my cock enter Sierra’s rear passage ever so slightly. My hardness was slicked down with her juices, so I knew we were just working against the muscle constriction now. I pushed slightly and a little more gave way to a much thicker area on the head of my cock. I could feel it grabbing tight and squeezing me there.
“Oh fuck,” Sierra cried, and I could tell that this was a tough spot. I held completely still and waited while Rose helped ease the moment.
“There’s no hurry honey, we’re here for you. Just take your time and relax . . . open up. This is going to feel so good. We just need to get through this. Believe me it will all be worth it.”
Wait. Did Rose just admit to taking a cock up her ass? That little comment swelled my hardness to an even greater level, and I was sure Sierra could feel it, along with every beat of my heart in her tight, sexy hole.
“Oh Mom,” said Sierra nervously, “I’m not sure I can do this.” Her breathing was getting rough and her legs were still shaking.
“You’re almost there sweetheart, just a little more,” with that she stroked her daughter’s hair against her chest and looked at me with a subtle nod to “go ahead and push some more.” I did. My hard cock wasn’t backing down now, and as I pushed in a tiny bit, I pulled back the same.
I pushed again, just a little, and then let go. I kept this oscillating pressure going, eventually feeling my pushes getting slightly deeper. It was so subtle that I wasn’t sure if anything was happening, but then all at once the head of my cock popped completely in!