Gay Ladyboy Sex Experiences Stories

59 results
Orientation
Length
Category
Source
Infinite Scroll

28-year-old Bisexual Stepfather Ch. 19

by walterio on Apr 24, 2018
Gay Male

AUTHOR'S NOTE: This series contains straight sex, bisexual sex, gay sex and incest. DAY THREE -- PORT OF CALL SAN JUAN There was no sex in the morning as everyone had to eat breakfast and then meet the outfitters for the daily excursions. Margaret opted to do the tour of the old town and do some shopping in the city. Delia and Chole also joined that excurs...

Romeo, Where Art Thou Going in Life? Ch. 03

by walterio on Sep 14, 2017
Gay Male

ROMEO ACCEPTS MARCEL'S OFFER Romeo slept at the salon the night that he had been evicted form his home. He knew that he had no chance to go back home as his father would never let him return. The next morning Romeo freshened up at the salon and then headed to the barber school. He would return later that day to work at the salon and by then he hoped that he...

Colin's Bi-Sexual Side Of Life Ch. 04

by walterio on Aug 31, 2017
Gay Male

COLIN'S BIG BREAK Colin saw Ronnie, Ricky and Henri a couple of more times before the consulting engagement was concluded. He was in the home office on this particular Monday and he attended the staff meeting. It had been awhile since he had been at a staff meeting since he was out of town the previous Mondays. His boss Jim was out of town so Brad the secon...

The Real Thing This Time

by hornyrider on Aug 18, 2017
Gay Male

Readers of my story 'My First Ladyboy' will know that I was spending a lot of time in the Far East monitoring the activities of my company's agents from our London base. The initiative proved highly successful and it came as no surprise when it was decided to establish a small office within the region and I was asked to set it up. I was instructed to make...

Lexius Academy for Boys Ch. 03

by walterio on Sep 14, 2017
Gay Male

NOTE: This story contains gay sex and sex with a lady boy. ***** FRIDAY PRACTICE FOLLOWED BY FUN On Friday afternoon, tennis practice was light with focus on ground strokes and serves. After practice Coach Andrews announced the strategy they would use against Manchester Academy. He knew there was no way they could beat them head to head, so he shuffled hi...

The Booth Ch. 1

by C_Duke on Sep 2, 2017
Gay Male

I don't see any shame in admitting bisexuality. The truth of the matter is, I find women attractive, and sex with them highly pleasurable. In fact I'm thinking about them and it most of the time, like most guys. But recently, and essentially through my exposure to more, harder and more varied porn I started to wonder. And then I started to really think ... a...

Lexius Academy for Boys Ch. 02

by walterio on Sep 14, 2017
Gay Male

SHARING STORIES Brandy and Robbie were cuddled together in Brandy's bed on Saturday morning. They had had a successful start to the tennis season on Friday. The team won all five matches defeating the other school 5-0. Carl the number one singles handily won his match 6-2, 6-2. Jack the number two singles won 6-4, 6-3 and Kyle won his match 5-7, 6-4, 6-1. T...

Seduced by a Friend Ch. 03

by yorie on Sep 14, 2017
Gay Male

Following the painful fucking with Howard and John at Dave's place, I swore I would never go near gay sex again; I could not come to terms with what I had done, and had done to me. I was very disturbed about the day's events and the intense pain I got when Dave brutally fucked my ass for over an hour. All I could remember doing was absorb the pain, and keep...

A Teen Seduced and Hooked on Anal Ch. 10

by walterio on Aug 12, 2019
Gay Male

SATURDAY MORNING FILMING Bruce the director met with the three actors. Eric, a beautiful blonde Carrie and the pretty ladyboy Carla. He explained that neither Eric or Carrie were to know that Carla had a dick so they were to act surprised when they saw it. They had met at a club and Eric had invited them back to his place. Bruce asked Eric a special favor....

Where the Girls Aren't

by MWDK on Sep 25, 2017
Gay Male

If there's a commonly reoccurring theme to my existence it is one of overbearing responsibility, doing the right thing, taking care of others and eschewing the thing that I might want for the thing that is most practical or more socially acceptable. All in all, it's not a terrible perspective on it's own but as with everything - moderation is key and without...