My current boyfriend is really into different kinds of roleplay. He asked me if I’d like to get into some costumes, as he’d really like to buy me some. I said Sure, order whatever you’d like. We could make it fun. He ordered a schoolgirl one, a nurse one, and a few others he hasn’t shown me yet. The schoolgirl one was a lot of fun. He wanted me dolled up like in the Britney Spears music video. I did, and it was a lot of fun. Naughty fun! He tried to play the school principal I’d gotten sent down to. I’d been caught cheating, and he was going to punish me, which he did.
He had me bent over his desk and said he was going to spank me with a paddle. He did indeed have a paddle in his desk drawer, which he took out and showed me. And He told me to hike up my little plaid skirt and pull down my white cotton panties. I did as I was told. I knew I’d like this teacher-student roleplay when he showed me the outfit. AI bent over, grabbed the top of the desk, and waited for him to spank me, and he did. I got a half dozen swats with that paddle. He told me this would teach me not to cheat again, as this is what happens to cheaters that were caught.
Then he kicked my ankles apart and plunged his dick in my dripping cunt. The desk shook slightly with each thrust into me. I was creaming down the insides of my thighs. The spanking had made my buns sting, but in an arousing way. It heightened the sensations of him fucking me so soon afterwards. I was his schoolgirl slut, even if it was only role play. He grabbed my breasts, squeezing them, pulling me hard back onto him and his cock. My orgasm rolled over me like a wave. I screamed as I came on “my principal’s” cock. Fuck it was hot! It was a very sexy experience, and I was looking forward to the next time we played like this.
A few days later, he had me take the lead in the roleplay as I was dressed up as a slutty nurse. Stocking tops exposed, tits spilling out, wearing a little cap. He wanted an exam, and I was to examine every inch of his cock. I measured it, got him hard, measured it again. I told him the doctor requested a sperm sample. So I could either get it, or he could provide it while I observed. He requested help. He said it would help if he could see my tits as he masturbated, so I unzipped the uniform. My breasts spilled out, and he reached over to fondle them as I held the collection cup in my hand. It didn’t take long for him to spill his load into the cup. When it came to roleplay, anything goes.
He said he was still horny and could produce more sperm. He thought a prostate massage might do the trick. So I slapped on a pair of latex gloves and lubed them up. He bent over the exam table, in reality the bed, and I inserted two fingers inside of him. He was hard again in a moment. I knew he’d shoot again, so I told him to hold the collection cup under his penis. A few strokes of my fingers on his prostate and he was shooting even more cum out. The medical role play was a success. He said he hadn’t cum that hard in months.
I’d been a bit reluctant to try this costumed roleplay stuff at first. He made me see, though, how it can enhance sex and make it a more exciting experience. There’s thought that goes into the scenes and costumes, how you’ll play your roles. I really did enjoy it and might even come up with an idea or two on my own to try out. Every role play might not be a hit for both partners. Experimenting and finding out can be fun and open your eyes to a whole new area of sex. One that you might not have explored before. I’d love to hear about some of your favorite scenes, and I can tell you some of mine. Let’s have the best phone sex ever!
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Skye is truly amazing. Her roleplay of being my sex therapist is almost heart stopping as she gets me so excited. I call every two weeks for a therapy session and can’t wait for 14 days to pass!
Exceptional call with Dakota. What a sexy call and perfect role play. She is Quite the keeper.
I’m physically incapable of producing semen anymore, but Dakota managed to create some for the first time in more than a decade. She is magical. If I were allowed to fall in love, I would!!
I had a wonderful call with Jade tonight. Each and every time is a great time. She really listens and that makes everything better. Thank you Jade ❤️
Megan is Amazing. If you want to cum hard, call her and get ready to cum like a rocket. She’ll do just about anything.
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Anna was great and open minded. Been calling for years and this was our first call. I will be calling her more going forward!
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