An Unexpected Birthday Surprise at Home
Part 4 of 5. So I ended up moving in with my best friends dad. As we would fuck he began dressing me up more and more he bought me wigs and make up and had me start hormone therapy. I began to dress
An Unexpected Invitation After School
Part 3 of 5. Right as my friend and I finished getting him packed up and all his stuff in his car his dad got back home. We both said goodbye and my best friend left to go back to school. His dad
An Unexpected Visit to a Best Friend's House
Part 2 of 5. So the next morning after my 21st and after getting fucked for the first time from my best friend's dad, I got up and went home to my apartment and showered then rested the rest of
A Surprising Hotel Room Meeting
(Away on business Mwm 50s, couple in their 40s) Back in the day (10 yrs), a couple answered an ad placed. After an email exchange and a call they arrived to my hotel room early the next morning.
Posted by a straight man
By Deleted User
An Unexpected Meeting at the Super 8
Posted as a 21 m looking for a bottom. A CD hit me up really fast and told me to come to a super 8 right next to my house. I’m there within 15 min. She’s wearing a black bra, with a lacy
Posted by a straight man
By Deleted User
An Unexpected Meeting with the Neighbor
Nice afternoon out, finally alone, I decide it’s a good time to play in the yard. I take off all my clothes, grab a butt plug, some lube, and a paddle. I get on my knees, ass up. Lube up the
An Unexpected Encounter During Lunch Break
Well it was a few years back, I was at work. I was extremely horny. I was actually thinking about snicking off and jacking off somewhere. I mean my balls were aching. Anyway I was in my office and
An Unexpected Surprise Visit from a Friend
Well back to the story so with my stepdaughter out of town for the weekend I have my TS lover spending the weekend with me we are having a great time together playing with each others body and
A Surprising Reunion with a Family Member
I have multiple ads here n presently live now I posted as a total bottom n discreet Latino crossdresser I have been here for about a 2 years .Well one nite I was dress fully putting together another
An Unexpected Encounter with a Roommate
I consider myself a straight man. I have zero interest in any type of a romantic relationship with a guy. But every once in a while I get the urge to have my cock sucked by a guy. Guys are just
A Journey of Self-Discovery and Transformation
Hi I'm very straight acting n share my life with my wife for many years, and use to sneak out to suck cock n get fuck ,without protection and came home with my ass full of cum I felt kind of
An Unexpected Visitor in Chicago
I am an attached, straight woman who has always appreciated the body of women. Recently, I found DoubleList and had been using the site to find women who I could taste. Last week, a tall brunette who
Posted by a straight woman
By billa1
An Unexpected Connection at the Store
Where to start. I am a 54 yr old sissy bottom who is a non-passable crossdresser. I have been crossdressing for the last 3 years. I wear mini skirts, dresses, stockings, daisy duke shorts, stockings,
Posted by a TS / CD
By Deleted User
A Straight Man's Unexpected Journey of Discovery
I have been a totally straight guy, married twice, up until recently. My wife had lost total interest in any and all sex, so I began to post ads looking for other women, and for a while at first, I
A College Girl's Journey to New Connections
I was a young 20 year old college girl when I first tried out double list. I had a great boyfriend, but he was a conservative, no sex before marriage type. Even though I loved him, I just needed a
Posted by a straight woman
By Deleted User
An Unexpected Adventure Behind Closed Doors
I love getting my cock sucked as often as possible and am always looking for adventurous new guys here on DL. I posted an ad looking for some head one day and this totally hit beefy daddy hit me up
A Weekend Getaway with My Stepdaughter
Well it has been a few weeks now but my stepdaughter and I have been busy with each other playing together lots of foreplay and roleplaying going on
She decided she was going to KW this weekend to
Unexpected Connections at the Korean Spa
Posted on DL that I’d be stopping in on the local Korean spa, which while isn’t a bathhouse, but trying to be more of a legit spa, clearly has its fair share of anonymous hook ups. All
Unexpected Encounter in a Hotel Room
I’m a happily married guy but I don’t always get enough at home so I hook up with women and occasionally a guy on the side. I put an ad up not really expecting I would get a reply. I
Posted by a straight man
By Deleted User
A Couple's Journey into New Experiences
We're a couple in our late twenties. We were having having some drinks one night after dinner and playing Truth or Dare. I guess I had to much to drink to drink and when I got hit with Truth I
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