Bob Long

Here you can find all stories written by Bob Long. Please leave a comment and rate the stories to show your appreciation.

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Not much to tell, one day while rehabbing from an accident which made it difficult to have sex my wife and I were reminiscing about some of our sexcapades so she suggested I start journal of sorts and if I felt so inclined share them online. All of my stories are 100% true, I am in no way shape or form a writer I actually hated HS english class except for the hot hippie teacher who always wore mini skirts and for the most part went braless

8.6
15 Votes

My wife watched as I got fucked by a big cock (ch. 2)

16 Feb 2021 5469 readers comments 23 Min Read

Sorry this took so long to post but with everything thats been going on in the world I hadn't had time. This is the follow up to on my encounter with Dave my wife's friend who helped her get revenge on my for having some rough sex. As always this is 100% true and factual with the exceptions of the names of the parties involved

Topics: Anal Sex, Crossdressing, Prostitution, Oral & Blowjobs

8.9
29 Votes

My wife watched as I got fucked by a big cock

25 Sep 2020 17896 readers comments 17 Min Read

This is the true story how my wife thought it was time I learned a lesson and this was her payback for the things I made her do and took for granted

Topics: Anal Sex, Straight Men, Voyeurism, Punishment, Bisexual, Oral & Blowjobs, Cuckold, True Story, Pegging

8.4
12 Votes

The end of a perfect night out as a sexy woman

1 Mar 2020 3222 readers comments 11 Min Read

This was the last but ultimately the best part of evening when my girlfriend took me out to a gay club, dressed as a woman just to test the water and to assure me that I not only very passable but also pretty damn hot. I got way much more than I imagined

Topics: Anal Sex, Crossdressing

7.8
30 Votes

Before she turned me out

10 Feb 2020 7578 readers comments 49 Min Read

My girlfriend who fostered my obsession with crossdressing and living as a woman, trained and made me into one hell of a beautiful woman who eventually sucked a mans cock and loved it

Topics: Anal Sex, Crossdressing, Transgender, Oral & Blowjobs

8.1
15 Votes

How I got started (ch. 3)

5 Feb 2020 1072 readers comments 18 Min Read

Our continuing story of the greatest time of my life exploring and fulfilling my deep seated desire to be a woman through crossdressing and learning about my sexuality with the best teacher in the world my mom

Topics: Crossdressing, Incest, Oral & Blowjobs

7.8
4 Votes

How I got started (ch. 2)

4 Feb 2020 1875 readers comments 22 Min Read

This is a continuation of my glorious introduction to crossdressing and sex

Topics: Crossdressing, Rimming

8.4
81 Votes

My First time with a man

2 Feb 2020 6611 readers comments 14 Min Read

An encounter that just happened after years of repression

Topics: Anal Sex, Crossdressing, Big Dick, First Time, Oral & Blowjobs

7.3
40 Votes

Parking lot blowjob

1 Feb 2020 9037 readers comments 24 Min Read

This is the story of how my ex girlfriend, made it her mission to get me to suck a guys cock

Topics: Black Men, Anal Sex, Crossdressing, Handjob, Rimming, Spanking, Role Play, Oral & Blowjobs, Cuckold

8.0
130 Votes

How I got started

30 Jan 2020 10353 readers comments 12 Min Read

This is how I began my life as a crossdresser, encouraged by my mother who lovingly guided me and embraced my desires to dress as a women

Topics: Crossdressing

8.2
49 Votes

She turned me out

13 Mar 2019 8953 readers comments 26 Min Read

My girlfriend not only encouraged my crossdressing but how she turned me into the cock sucking whore I am

Topics: Black Men, Anal Sex, Crossdressing, Handjob, Rimming, Spanking, Role Play, Oral & Blowjobs, Cuckold