Gentle, but thorough

I don't know exactly what Alison had in mind when she scurried up the stairs to her room, but I'm not expecting to see her crouched timidly on the floor wrapped in only a sheer white wrap.

“Please, My Lord.” Alison looks up at me fearfully and pulls her wrap even tighter around her breasts. “No man has ever seen me like this.” Considering that fewer than three minutes ago she was kneeling naked at my feet and stroking my cock, this is a shift in her little role play, but I don't mind.

“Get on the bed, girl and spread those pretty little legs.”

“Please, Master. Have mercy.” It's tempting to throw her roughly on the bed and ravish her as she screams and begs, but instead of '****' her I choose a gentler option.

“Easy princess. You're my handmaiden now, remember?” I brush the back of my fingers along her bare shoulder and smile when she jerks nervously like a skittish kitten. “I'll make your first time one that you'll never forget.”

“I'm scared, Sir.” Her great big eyes lift to meet mine, “I know now what a man does to a virgin like me; I saw what your warriors did to my ladies-in-waiting.”

“It doesn't have to be like that. I'll be gentle.” She blinks away imaginary tears and lets me lift her to the bed. In a lovely display of modesty, Alison clutches at the sheer fabric when I start to unwrap my prize. “Everything will be fine, little one. Let me see these lovely treasures.” With only a moment of hesitation, she lays back on the bed and lets her hand fall to her sides in a final submissive act of surrender.

I've always known how beautiful my tenant is, but when I peel away the covering and see her lying naked on my bed, I am reminded again that I am the luckiest man in the world. I strip off my remaining clothes and lay by her right side so my right hand has unobstructed access to her body. I spend a few minutes stroking her soft breasts while I kiss her ear and neck making her moan sweetly and squirm on her back. When my hand leaves her breasts and heads down over her firm belly, she tenses up again crossing her legs tightly as if that was going to stop me.

“Please, Master ...” I had forgotten that I was supposed to be 'deflowering' this pretty virgin but clearly Alison hasn't. “I can't do this.” Her naiveté makes me smile, as if my pretty handmaiden had any choice now that she is naked in my arms.

“Spread your legs.” It is a soft whisper, but it makes her whimper wordlessly before slowly uncrossing her ankles and spreading her knees outwards. Now my hand can move between her legs and I tease her for a good three or four minutes as she moans and writhes beside me. Only when she is all but begging me do I roll on top of her and take her head in my hands forcing her to look at me. “Look at me.” This time my order is more demanding, “I want to see your eyes when I claim you.”

The moment is as sweet as I hoped, Alison plays the part of the virgin perfectly. Her eyes widen when she feels the head of my cock find the slit between her petals biting her lip between her teeth as I get ready to claim her. The sharp gasp of pain when I push into her would certainly have fooled me if I didn't know better and I pause to make sure I'm not hurting her.

Fran had been a virgin when we made love for the first time, but I was just a clueless college Junior and didn't appreciate just how special the moment was, even after waiting almost a year before she agreed to sleep with me. This might be even better than that first time; Alison's pussy was certainly nice and tight and her little squeaks and whimpers as I push in and out of her just adds to the illusion. All the good parts of 'popping a cherry' with none of the pain or blood. Damn it feels good.

“Oh, my Lord ...” at first, I can't tell if Alison is praying or speaking to me, but then it becomes clear. “It's starting to feel good, Master. It hardly hurts now ... Oh ... Oh wow!” I remember thinking when I was climbing the stairs that I could always pull out when it came to that time, but there is no way my seed is going anywhere but my 'handmaiden's' womb and damn the consequences.

Alison stiffens under me when she feels the heat of my cum start to fill her, but she doesn't protest or try to push me off her. She lets me fill her even though I might be ruining her life with an unplanned and unwanted pregnancy.