Truth or Dare (part two)

A sexy boudoir photoshoot.

Continued from part one

“Uh, I beg your pardon? Are you being serious right now?”

Shawna scoots closer to me on the couch, making my heart stop during mid-beat. I can feel the heat emanating from her body. She pats my right knee and tickles my thigh. My breathing stops. Then she leans over and kisses my neck. The hairs on the back of my head flutter in response. Her musky smell is unmistakable, yet it’s as sweet as perfume.

“Deadly serious, sweetheart,” she begins. “Like I said, I’m feeling adventurous tonight. What do you say?”

What else can I say? I figured I’d never be able to go “all the way” with her ever, but apparently tonight is my chance. Well, if you consider anal to be going all the way. Which, considering my dick hasn’t penetrated her at all up to this point, it sort of is. So what do I have to lose?

“I’d love to! Yeah, let’s do it.” With that reply of affirmation, Shawna excitedly gets up and scurries to her bedroom.

“Wait here, darling! I’ll be back in a jiffy.” Nervously, I remain seated on her sofa. My toes have curled up tightly, a sign that I’m feeling anxious. Can you blame me?

After what seemed like an eternity, Shawna returns to the living room with a bottle of scented oil. Peach seems to be what she selected. I’ve never seen her this giddy before! Her gorgeous eyes are open wide, she’s fidgety, and she cannot sit still to save her life. I can only imagine what the next few minutes are going to be like…

“It’s been a long time since I’ve done anal, but I know my body pretty well,” she says. After nodding her head at me, I begin to undress. Shawna is wearing sweatpants and an old college t-shirt. She’s already barefoot. I neatly pile my clothes in the corner of the room, with my phone and wallet lying on top if it. I’m already erect, which should come as no surprise to anyone. Soon, Shawna is completely nude as well. And she looks just as gorgeous as ever. She’s squatting heavier right now, which is evident by the advanced thickness of her thighs, hamstrings, and butt. God, her butt is perfect. So shapely, rounded, and full. I cannot believe I’m about to enter it in a short while.

Shawna isn’t wearing any makeup, which doesn’t matter because she’s a natural beauty. I swear she’s even more beautiful without makeup. But maybe I’m biased because I like her so much. She spreads a few blankets on the floor with the reverential meticulousness of a religious ceremony. Finally, she gets on her knees and wags a finger at me. I sit down next to her. We kiss. She strokes my hardened penis, tickles my scrotum, and sticks her tongue deep inside my mouth. Before I penetrate her, she wants to penetrate me first. She’s marking her territory. I do nothing but surrender to her authority.

Jessica Williams looking as hot as any woman can possibly look.

“The key to successful anal sex is adequately preparing the anus,” she explains with the serious candor of an academic. “Let’s oil up your fingers. Then, I want you to open me up.” Shawna dabs some of the sweet fluid onto my fingers. I cannot think. My brain is frozen. I can barely move. I need her to take control because I have no fucking clue what I’ve just gotten myself into! Next, Shawna gets on all fours and sticks her perfectly sculpted ass upward. My hand dripping with scented oil, I take a deep breath and observe where my fingers are about to go.

Her anus looks pretty.

Yes, that’s a rather strange observation to make, but it’s true. It’s dark brown. It’s small. It’s tight. It looks like a cosmic black hole, which is funny unto itself. She shaves her pubic hair, so the surrounding area is as smooth as it can be. Hesitantly, I stick my right index finger inside her. Slowly. Thankfully, I clipped my fingernails earlier this week (coincidentally, of course) so there’s no risk of inadvertently injuring her. I would never want to cause her any pain. Shawna moans in response to my penetration, which I hope is an indication I’m doing this right.

“Do you like that?”

“Yes, I do darling. Thank you!” Emboldened, I stick my entire index finger up her anus. It’s as tight as I’d imagine it would be. Shawna is breathing rhythmically, which keeps her relaxed. I stop, not knowing if I should continue or not. But she isn’t giving any signs that I’m hurting her. Then, I slowly stick my middle finger inside her, with my index finger still there. She groans louder, but still isn’t showing any hints of pain. I playfully experiment with thrusting my fingers in and out of her. In and out. In and out. Rhythmically. Leisurely. Shawna purrs like a kitten.

Hey, I think I’m getting the hang of this!

I move my fingers in a circular motion. She doesn’t speak. I can’t see her face, but I’m guessing her eyes are closed. She’s drinking in this moment. She’s feeling every sensation and treasuring it. Finally, I thrust my ring finger inside her, making it three total. Shawna is in heaven.

“Oh, fuck yeah…!”

Shawna rarely swears. She grew up Presbyterian, after all. So if she’s casually dropping the f-bomb, that means something.

“Oh, baby, you know how to please a lady.” Shawna drops her butt close to my knees. “I think you’ve adequately prepared me. Now let’s prepare you…”

She reaches over and snatches the bottle of oil. I hold my breath. Shawna drips a small amount onto her fingers, wraps them around my erection, and moistens me up. I try my hardest not to accidentally come prematurely! Once my manhood is glistening with lubrication, Shawna declares her desire to get the party started.

“You’re now ready. I’ve been ready. Let’s do this.”

Autumn Raby looking ready.

Oh boy. This is it. For all the marbles. It’s Game 7 of the World Series. Bottom of the 9th. Two outs. Down by three. Bases loaded. 3-2 count. This is where I need to come through in the clutch. This is my time! Time to prove my worth!

Dear God. I need to stop being so damn overdramatic.

I close my eyes, sigh, and open them slowly. I take a moment to observe how the light shining from the nearest ceiling fan perfectly shows off Shawna’s big muscles. They’re curvy, hard, strong, and unmistakably feminine. She’s breathing deeply, almost like she’s preparing to meditate on top of a snow-capped mountain for the next twenty years. I can feel my heart pounding a million beats per minute. Faster than a European techno remix album.

“What are you waiting for?” Shawna impatiently inquires. That wakes me out of my internal monologuing. I pat her on the butt for good measure.

“Uh, nothing.”

I pause. Then, I grab my penis. It’s still erect, as hard as it can be. It’s also dripping wet. With my left hand, I hold on to her left hip. Her denseness turns me on further. With my right hand, I grip the base of my penis. The tip hovers over her prepared entryway. Shawna’s breathing has steadied. I can stay like this forever, but that wouldn’t do either of us any good. So, I go in for the kill.

Gradually, I squeeze the broad head of my manhood inside her anus. It’s difficult at first, but the lube definitely helps. Shawna moans. I’m too nervous to feel any kind of pleasure. Once the whole tip is inside, I brace both of her hips and push in all the way. Inch by inch. As methodically as I can handle it. Once I’m completely inside, Shawna playfully wiggles her butt from side to side.

“Oh, damn. Mmmmmmm. I love this!” Shawna exclaims.

Fully confident, I move in and out of her rhythmically. She’s so tight, despite the work my fingers did earlier. Once I get past the initial shock of realizing that my dick is inside a beautiful muscular woman’s anal cavity, I begin to enjoy the experience.

“Ooh, this is different…” my braindead self observes aloud. “I also love this!”

Still on all fours, Shawna’s moans turn to growls. I cannot even begin to describe the noises I’m making. We must look like wild animals mating in the jungle. The primitive position we’re in, mixed with our involuntary guttural noises, is very beast-like. But we are two wild beasts. In this moment, Shawna and I are no longer human beings living in the civilized world. We are primordial creatures experiencing selfish pleasure for its own sake. Shawna has stopped moving, choosing to only experience my thrusting. My pace quickens in anticipation of my inevitable climax. I don’t know how much longer I can hold on.

“Oh fuck!” Shawna screams.

“Ohhh!” I also scream.

One final powerful thrust later, I collapse on top of Shawna’s massive body as I empty myself into her. On and on my spurts last, as if she’s draining every drop out of me. She can have all of it if she wants. Shawna falls to the floor on her tummy. Her heavy breathing lifts me off the ground – up and down, up and down, up and down. We stay like that for several minutes. I lean over and kiss the mounds of her back muscles. She’s as wide as a freight train.

Whew.

This is what Shawna’s living room looks like.

Eventually, I roll off her. We face each other on our sides on top of the blankets. My softened penis dangles freely. Shawna pinches it playfully. One last tiny drop of semen leaks out. It drips onto the blanket. Shawna giggles. Then we kiss. The tips of our tongues do a little dance. We continue to kiss for the next four or five minutes. When will we stop?

Finally, Shawna stands up. She rubs her sore anus and twists her torso from side to side, causing her back to make a distinctive cracking sound. She groans in pain. I cannot believe how loud it is! I guess all those years of heavy weightlifting has taken its toll on Shawna’s body. Her physique is eyepopping, but it does come at a cost. She then notices me noticing her back cracking. I can tell she quickly wants to change the subject.

“That was amazing, darling.” Shawna leans over and kisses me, possessing me with her lips. After her momentary display of vulnerability, she wants nothing more than to reassert her power and dominance. “I need to clean myself off. But when I get back, it’ll be your turn in our little Truth or Dare game. Be right back!”

Shawna disappears into the bathroom. I remain on the floor, laying on top of a pile of comfy blankets. But I cannot help but still think about what just happened. For the first time ever, Shawna was vulnerable. She looked insecure. Was she thinking about aging? Is being with me a reminder that she’s no longer a young woman, but a woman approaching middle age? Like I said before, I have no idea how old she is. But she must be 15 or maybe 20 years older than me. She’s as gorgeous as a supermodel and the crow’s feet around her eyes do not diminish her considerable beauty one bit.

A bottle of sensual oil.

Hm. Maybe I’m overthinking things here. Which is funny considering I just made love to her!

Well, anally made love to her. Which is the same thing, right?

Uh, right?

My train of thought is shattered when Shawna sneaks up behind me and lifts me up off the floor. I gasp. She kisses my neck and playfully wrestles me onto the couch. We laugh. After a few moments of silence, I finally speak.

“Okay. You gave me a dare. I’ll give you a truth. Are you ready?”

She sits up and crosses her massive legs. “Ready as I’ll ever be!”

“Great,” I begin. I take a deep breath to gin up the courage to ask my question.

“Does size matter?”

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