Chantelle Gets To Play

by Chantelle

Gender: Male transvestite
Age: 40
Race/ethnicity: Caucasian
Current location: Adelaide, Australia
Highest education received: College degree (eg., BA, BS)
Occupation: Office administration
Relationship status: Divorced
Religious affiliation: Christian
How religious are you?: Not at all
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bi sexual when dressed as a girl
How many sexual partners have you had in your life (including oral sex)? 50
How many hookup stories have you here posted before? Zero

Chantelle Gets To Play

How long ago did this hookup happen? 3 years ago

How would you best classify this hookup? Booty call

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Older than me, mid 50’s, tall, dark hair, handsome. Dominant personality, did not know him at all before he contacted me on line, I was genuinely excited about meeting him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Met him on line on an adult dating site, exchanged emails then mobile numbers, spoke for a few weeks then when I felt comfortable invited him to my place. He made the initial contact and I was happy to develop things. He has a dominant personality and Chantelle is submissive so he really appealed to me, also he clearly had a passion for transvestites.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? He texted me a few days before and gave me a detailed description of what I was to wear- knee high boots/corset with stockings/black lacy matching bra and panties/short black dress/DD false boobs/long straight red wig/heavy makeup with long false eyelashes and long red false nails. I remember getting butterflies as I got myself ready, he called me as said I was to walk to his car and get him, he had parked 500 meters away so I had to walk down the street to him, humiliating but I loved it. He got out told me I looked beautiful and kissed me full on the lips with tongue, I just melted into his arms. We walked back holding hands and I made coffee but my hands were shaking I was so nervous/excited, I sat next to him on the couch and he touched my leg then lifted my dress and told me I was a good gurl for wearing what he had asked for. We kissed some more and he told me to take him to my room and model some different outfits, I was so turned on as he lay on my bed and I took off my dress to show him the underwear he had told me to wear, he asked me to put on a pair of pink panties which I had laid on the bed and as I stepped out of my black ones my rock hard cock was on display, he beckoned me to him with his finger and I walked towards him feeling like a truly sexy gurl, he sat on the bed and I stood in front of him and he started to play with me and finger my anus, I was watching it all in the wardrobe mirrors and I could see by my face I was loving it. I pushed him back on the bed and asked if I could suck him, almost as soon as I put it in my mouth he came and I swallowed it all, we then returned to him fingering my anus and masterbating me. The orgasm I had was and still is the strongest one I have ever had, I came all over his arm and hands and he said “good girls eat this up” and I did something I had never done before and licked up all my own cum. I felt really strange after I had cum and asked him to leave which he did with no fuss.

Did you have an orgasm? Did your partner(s)? Yes I had an amazing orgasm and he came very quickly

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None initially but he wore a condom for future encounters for anal

What were your REASONS for having this hookup? Exploration of my bi side when dressed as chantelle

Were alcohol or drugs involved? If so, how much? no

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I felt strange and a bit guilty but glad I had done it, we hooked up 5 more times and had anal sex the last 3 times (me as the bottom every time) which I really enjoyed

To whom did you talk about the hookup? How did they react? Told a cross dresser friend, they thought it was good I was exploring who I am

Was this a consensual and/or wanted experience for you? For your partner? Consensual and wanted for both

Do you regret this hookup? If so, why? N/A

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best thing was embracing my feminine side and being with an Alpha male who saw me and treated me as a sexy girl.
Worst thing was the feelings of confusion and guilt after (got less after each time)
Was fun and I have since had a few casual but regular experiences with great guys
Has made me realize I am heterosexual when “boy” me but bi and attracted to men when I’m “girl” me

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? I found out the importance of exploring your sexuality in a safe planned way and that it has given me a real insight into my Male and female sides

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