Crossdressing Teen with Step-Dad part II

This is a continuation of my previous story – link in comments.

A few months have passed since my first night with Chuck. Our relationship has noticeably improved, as my Mother has even made a comment or two. I’ve started my senior year in high school. Thanksgiving is soon around the corner. Chuck has become accustom to receiving blowjobs from me regularly. At least twice a week, he visits my room with a light knock on the door. One particular night was different though. He knocked and entered, presenting me with a gift. He set it on the bed and said he’d like to see it on me, he said he’d be back in a few minutes.

I open the box to find a very nice piece of lingerie. Of course, I immediately try it on. It’s the first thing Chuck has given me, probably ever. A few fleeting thoughts of guilt cross my mind. I push them away with the thought that if my Mom were taking care of him better, he wouldn’t be watching porn and in-need of blowjobs from me. Blowjobs that I’ve greatly improved on with practice. Chuck has been praising me for the skills I’ve gained. The lingerie is a black Barbie-doll cut with a frilly skirt. A skirt that don’t quite cover my ass but, that’s probably the point. I wonder if tonight is the night he plans on taking my virginity. I’ve been scared and excited in anticipation. I know once he does, I’ll be his and that scares me. As much as I enjoy our naughty times, Chuck has a serious dark side. He’s forced me to give him blowjobs in public parking lots and in the living room while Mother cooks in the kitchen. It’s only a matter of time before we are caught but, it does add to the excitement.

Another knock at the door comes and Chuck walks in closing the door behind him. He is staring at me, amazed at how well the lingerie fits I guess. “Stunning, can you spin for me?” he asks with a grin. I indulge and give him two quick twirls. The already short skirt lifts even higher with the movement. “That’s my girl” he says as he walks up to me and puts his rough hands on my shoulders. This is his signal for me to get on my knees. He gently applies pressure down on my smaller frame.

I look up at him from my 5’8’’ stature to his 6’1’’. He’s wearing his standard sleeping attire, boxers with nothing else. His stomach overhangs his boxers a little. He’s not grossly overweight, just about 260lbs, if I had to guess. My 110lb frame provides little resistance as I slowly drop to my knees, while maintaining eye contact. I thought I wouldn’t be nervous about giving Chuck blowjobs anymore but, every time, I still get the jitters. I tug at his boxers and they quickly fall to the floor. Something is different though, he’s not hard.

I look at him and quietly ask if he thinks I’m pretty? He brushes the hair out of my eyes and says, “Don’t worry, he’ll come alive in your mouth.” I smile and reach for cock while parting my lips. I sense something different though. He smells different, musty, and I hesitate. He sensed my hesitation and guided my head onto his cock with some force. I quickly found out that his cock tasted different as well. Chuck lets out a low moan while I fondle his cock with my tongue. I can feel him starting to grow now.

Once fully erect, he ask me if I know what that taste is on his dick. “That’s your Mother’s juices, how’s that taste?” I’d never had the pleasure of actually being with a woman, the extent of what pussy taste and smells like has been limited to my Mother’s dirty panties. The same ones I would wear and cum in while doing my crossdressing rituals. How did I not recognize that smell? Why is he having me suck his dick after he’s fuck my Mom? Is this another step in his efforts to humiliate me? Why is this turning me on even more? All these thoughts are running through my head while I continue to suck on Chuck’s cock. I cannot control my urges as I continue to clean every drop off of his cock.

Chuck grunts as he pulls my head away from his cock. He tells me, “Tonight I’m fuck you like the slut you are.” I am in shock as I look up at him, still on my knees. He steps back and motions for me to bend over the edge of the bed. I try to stand but my legs seem to be jello. “I hope you’ve been preparing yourself, you know this has been coming.” I nod as he helps me up, gives me a kiss and gently pushes me over the edge. I squeak, “there’s lube in the top drawer.” I hear the drawer open and click of the bottle cap open. A cold quirt of liquid on my asshole makes me tense up for a moment.

“Just relax, you’ll get use to in after a few minutes.” He says with a reassuring tone. I grip the covers on the bed as I feel him position himself. He gently starts applying pressure and the head quickly slips into me. I feel his rough hands on my ass checks, spreading them apart. “Your Mother’s ass isn’t this tight” He touts as he slides back and forth, slowly getting deeper. I let out a large exhale as I feel him reach his end depth, of his whole 4-inch dick. Then I gasp as he quickens the pace. It’s not as painful as I predicted. Apparently, my practice the hairbrush handle has paid off.

The next few minutes pass somewhat quickly. I’m turned on by all his dirty talk, telling me how much better I feel than Mom. Then he tells me how she could take tips from me. This really turns me on and I start letting out some feminine moans to help finish him off. Chuck takes a few more power thrusts and lets out a low moan. He lays on top of me, partially sweaty, as his cock starts to soften and slides out of me. Chuck kisses my neck as he starts to roll off of me. I lay still, probably from the shock and disgust of the last few minutes of my life.

Chuck slaps my ass like always and then says, “I hope you enjoyed that as much as I did.” As he walked out. I felt disgusted and totally used. I loved it. After that day, I started fantasizing about taking Mom’s spot in bed. Possibly making her a cuckquean and I would be Chuck’s sissy cuckcake.

Source: reddit.com/r/eroticliterature/comments/7249c7/crossdressing_teen_with_stepdad_part_ii