199 | Submissive Sissy in Pantyhose: Jay’s Sex Stories

Jay (30s Bisexual Latin dude) has a wife who doesn’t know he’s a cross-dresser. In their sex life, he is a dominant, macho New Yorker (who sometimes buys her lingerie he later opes to wear)—but when she’s away on work trips he transforms into a submissive housewife, his sexiest self. Jay shares details of dressing up: his favorite shade of red, heels, shoes, and stockings, how his 6th grade teacher inspired his curiosity around pantyhose, and how aroused he got the first time he borrowed some of his mom’s to try on. He talks about early hetero dating and imagining being the receptive, more passive partner, and shares how his private transformations into a femme babe led to evolutions of his sexuality, including becoming increasingly open to offering blowjobs and receiving anal. He shares stories of exploring first online and eventually in-person crossdressing community, times he rented a hotel room by the hour and invited guys to stop by, a random encounter with a mindfuck Dom, running into people he knew while dressed up at 3 AM, and how camming has allowed him to explore his sissy side while maintaining the agreements of his monogamous marriage. He describes the straightforwardness of his visually-oriented foreplay- and sensual-loving dominant dude mode, and then tells us the detail of his peak sissy submissive self, and the inspiration he would take from his engaged audience while camming—from playing with himself, to riding his dildo, to giving himself a facial, and his evolving exhibitionist self. Other topics include learning to tuck, dress-up specific dirty talk, cum play, messy makeup, BBC dildos and MILF porn, driving in heels and making out until his mouth was sore.

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