Hello everyone. If your new here then you can get caught up by reading my other posts, but if you don’t want to, I’ll go over some basics. I’m Ben, a 21yo submissive guy and I have a fetish for crossdressing and bondage (my fem name is Becky). My girlfriend Gwen is 21, supportive of my fetish but very new to it. I have been staying with my dad’s friend Jasmin for awhile now so my dad doesn’t have to worry about getting me sick.
I recently made a post were I asked for thoughts on if my dad or Zach was a better idea for Gwen to sleep with first and we decided that we will still start with my dad. She told me she feels more comfortable with him and it was our first plan so no change there.
So Zach has finally recovered and is back at his apartment. He was staying at his mom’s house while he was healing but he can walk just fine now.
Gwen called Zach to talk with him about sex in the future and Zach was unsure if she was alright with everything and she assured him that she was, and we would start with a 3 sum when she joined us but maybe one day he could fuck her 1 on 1. Unfortunately, Gwen’s mom heard some of that phone call and she thought Gwen was cheating on me. Gwen had to tell her that we were planning a 3 sum, which I’m positive was super uncomfortable and her mom was pretty upset with her and lectured her.
Gwen’s Note: My mom tries to be open minded but she is very conservative still. It all ended with “well you better not get pregnant and there is no way your doing it here! Couldn’t you at least wait til you and Ben were married?” So yeah that was a “fun” talk. About as fun as stepping on Legos. Anyways things are ok now.
Ben: So Zach didn’t feel comfortable coming to Jasmin’s house for sex since he doesn’t know her very well so he invited me to his apartment. Jasmin helped me get dressed, done up and groomed for my date and I drove over to Zach’s apartment. I wish I wore a longer skirt cause when I walked to his apartment it felt like my ass was hanging out and I’m afraid of his neighbors seeing me and thinking Zach got a hooker.
He answered the door and said “wow. You really do look sexy.” I knew I was blushing when he said that. Zach got a beer for each of us and we sat down on the couch. The drinks helped us unwind and he asked what we should do, so I just got on my knees and pulled his jeans down. His cock was really long and I quickly began licking and sucking it. I got him hard in no time and he was clearly enjoying all the tricks I was using. He got into it and stood up to start face fucking me, but before long he sat back down and told me to strip off my top and skirt, then get on the couch with him. I got on all fours wearing only my lingerie, hovering my fave over his dick to keep sucking it while he reached over me to play with my ass. It felt so dirty when he pulled out the butt plug I had in and when he asked if I wanted his cock in my pussy, my response was “fuck yes.” He laid on the ground and I mounted his shaft to ride his BBC like a real slut. I had my hands on the couch and coffee table for balance but I think I did a good job.
Zach surprised me by pulling my dick out of my thong and started jerking me out. It made me cum really fast all over his hand and abs. I said I was sorry, and he replied “well then clean up your mess slut.” I quickly got off his cock and licked my cum off of his body, then I sucked his hand clean. “Fuck I need to fuck you,” he growled to me before standing up, turning me and bending me over the coffee table. He pushed his big black cock right into my wet boy pussy and he fucked me relentlessly. I was moaning so loud that he told me to keep it down but I told him “I can’t help it, your cock is so good.” He grabbed my wet panties and stuffed them into my mouth as a gag and I loved how slutty I looked in the mirror while he destroyed my ass. I loved it and he made me sissigasm hard while he dumped a huge load of cum in my ass.
As soon as he finished, Zach stubbled back onto the couch and grabbed his thigh where he was shot. He must have been ignoring the pain and it made me feel bad so I jumped up to grab ice packs for him to ice down his leg. I sat there with him to help him feel better and we took a break to let him relax.
I had never been to his apartment before (He always came hang out at our house) and I got to say his man cave was so cool. He has a lot of similar hobbies to me and my dad so he had wrestling posters and games, but he also builds Gundam models that look so damn cool.
After we caught our breath on the couch with netflix, I kinda started cuddling with him and stroking his cock, and he asked if I was ready for round two. The obvious answer was yes and I mounted his cock right there on the couch. I rode his shaft like a slut and he asked if I wanted to show Gwen on the phone. I spun around and he set up his laptop webcam on the coffee table to take pics and record a video of me riding his dick like a whore. He shoved the panties back in my mouth and I went down on his shaft, making my breast forms and hard little dick bounce up and down. Then he pulled the panties out of my mouth to make me say stuff like “I love your cock in my boy pussy. Your big manly cock puts my tiny boy clit to shame. I love your cock more then any pussy. I love it when you make me your bitch.” He finally gagged me again and spanked me from behind (lightly) while wrapping his hand around my neck. I came so hard and then he bent me over the side to fuck me to quickly cum himself.
We were both worn out and I texted Gwen to tell her to find some privacy before we sent her something fun, and Zach asked “Oh I was just saying that to be kinky. You don’t have to do it.” I thought for a little while but I told him it was ok. “I want to be completely open with her so I still want to send them to her.” He pulled her up on FB and sent her the pics and finally the video. 5 minutes later, she sent us a short video of her fingering her pussy, then said “looks like you two had fun. I can’t wait til I get to go on that ride.”
We hung out for a while after that (bathed and changed) playing games and stuff, then I told him I had fun and left. It wasn’t nearly as awkward as I thought it would be and I am now so glad that he caught me.
That’s all for now. I hope you enjoyed the story. I am still working on the fiction story I started but it is so much harder then I thought. Stay safe and have a good day. Love you all.
Source: reddit.com/r/sexystories/comments/i8dpjl/my_first_bbc_ever_m21m33_crossdressing_interracial