He was such a cute girl (Part 4) [MM] [Crossdresser]

I kissed Chrissy down her body, licking her toned belly and her girly hips. She really had the tightest, cutest teen body. Now I was facing the real challenge of the night. I made myself courage and took off Chrissy’s panties, I wasn’t sure what to expect I mean of course I was expecting a dick though I had never had any experience with anything else than pussy until then. As panties came off, I saw a tiny little dick as well as small soft balls – no trace of hair whatsoever, or of any erection by the way. That dick looked so feminine to me, I found it oddly cute if that makes any sense. Chrissy smiled anticipating my next move. Now I don’t have an oversize horse cock, but the contrast and the size difference made me look like a male porn star, I was feeling like Rocco Siffredi out there! I went on my instincts and started rubbing my shaft all over her girly dick, then pushed my tip against her smooth little balls. I leaned on Chrissy and kissed her as she wrapped her legs around me, and kept thrusting my cock on her soft balls. You could almost say I was fucking her balls if that’s even a thing.

Chrissy was moaning louder now, trying to press her body harder against mine. It was clear that she was ready to be fucked. I took a large towel from the wardrobe and placed it on the bed as I knew things could get messy. As Chrissy lied on her stomach I took a bottle of baby oil and started rubbing it on her legs and butt. I started massaging her calves, then moving up to her thighs. Her skin was silky smooth and those lean legs looked even hotter shining in baby oil. I proceeded to rub her butt, that tiny ass was so soft and firm at the same time. I grabbed it with both hands and slid my cock between her butt cheeks – the old hot dog trick! I was hard as a rock now and ready to fuck that ass. I told Chrissy to get on all fours and she promptly obeyed. ‘Should I take my top off?’ she asked. ‘No’ I replied ‘Keep it on. It looks so sexy on you’.

I took a condom from the bedside table and quickly put it on. Chrissy was on all fours, only wearing her top – and her blonde wig – as I stood behind her, completely naked and with a giant erection. I squeezed more baby oil on her ass and between her butt cheeks to make sure her hole would be well lubed, then I gently slid a finger inside her ass. Chrissy was looking very comfortable with that so I started using two fingers, sliding them in and out of her hole. Her ass was begging to be fucked and my cock was eager to drill that ass. ‘Is this your first time?’ I asked. She turned her head back to me and smiled: ‘No.’ Look at shy, little Chrissy!

I got somewhat worried at that point as most of my past girlfriends didn’t enjoy anal at all, some would simply reject the notion while others were willing to try but usually struggled and found the whole experience painful and not really pleasant. Chrissy swept my doubts away as she spread her asshole with both her hands: this was the ultimate green light for me. I slid my cock inside her ass, slowly but steadily. That hole was super tight but I found surprisingly easy to push my cock deeper and deeper. There I was, standing on the bed drilling Chrissy’s ass as I gripped her hips with both hands. I went with the flow and started spanking her playfully on her butt cheeks, Chrissy was loving every second of it as she begged me to fuck her harder and faster. I happily granted her wish and started to pound her deeper and faster with each thrust, now I was really drilling that ass hard, my balls fiercely slapping against her butt cheeks as I picked up the pace.

Chrissy was moaning and screaming in pleasure, while the combination of fucking her tight little hole plus the vision of that shiny oiled ass were quickly leading me to climax. ‘I’m going to cum honey!’. I pushed Chrissy down and started to prone bone her, leaning on her with my whole body as I kept nailing her ass frantically. I came hard and fast inside her ass as I kissed her neck and gently bit her ear. I quickly pulled my cock out of her hole and got rid of the condom as we cuddled for a while, hugging her from behind and breathing her neck – she smelled like cookies! Her dick hadn’t seemed to get any bigger or harder during the whole time though she assured me this was a regular occurrence for her when she got fucked. She kissed me on the cheek and told me I was great and she enjoyed it so much. Oh well…

It was past 5 AM and Chrissy had to go back home now. Well she had to go back being Christian first: she sent me to collect her ‘other’ clothes in her scooter – parked just outside my house – while she used the bathroom. I quickly completed the task and left the bag with her clothes on the bed before going back downstairs. After a couple of minutes Christian came down too, now dressed as his ‘normal’ self, without wig or make-up. It was a bit of an odd situation, actually it was an extremely odd situation, we exchanged quick goodbyes and Christian left the place. As he briefly turned around smiling at me for the last time of that night, we both knew this was not going to be the last time for me and Chrissy.

Source: reddit.com/r/sexystories/comments/d4orfc/he_was_such_a_cute_girl_part_4_mm_crossdresser