I don’t consider myself gay either but I am a bottom for my trans girl’s big cock. I love sucking her or being fucked - as long as I get her cum!
First time with a man - story
- Thread starter IwantU99
- Start date
I didn't lose my anal virginity until my late 40s. I remember my three great fears: STDs, bleeding/damage to my rectum, and not being clean enough inside (that's still my #1 fear today). I found an ad on Craigslist for a man who was into bondage and enemas. I loved bondage, but wasn't into water sports, but I was willing give enema play a shot. So, I went to his apartment one afternoon. He was there with a friend, who was also into enema play. They were hosting a couple of other people for a play party. I was the first to arrive and they put me at ease by blindfolding me (my request; it never came off), cuffing me to the end board of their bed and feeding me their cocks.
When their friends arrived, the enema fun began. I was given a full bag of warm water and, after holding it for several minutes, I was taken to the bathroom to expel it. After several minutes there, they took me back to the bed, where I was given another bag. While I was waiting for the cramps to require me to evacuate, I heard a sloshing sound next to me: I later learned my bedmate was being given a good pounding while he was full of water. That explained the plastic sheet covering the mattress.
After my bowels were emptied for the second time, one of my hosts turned me over on my back and took my virginity. He was gentle and I didn't feel the pain I was expecting. In fact, it was more than pleasant and I was rocking along with him. He was kind enough to take a picture of the event; I still have it (and it proves he was wearing a condom). While I was nervous about it initially, the experience was, overall, very good, if unconventional (I rarely have had conventional sensual adventures).
Keep in mind, when you write, that no two deflorations are the same. And, if you want to add a dose of reality, you may want to have your virgin concerned about hygiene and tearing.
Let us know when you've published your story. I'm looking forward to reading it.
When their friends arrived, the enema fun began. I was given a full bag of warm water and, after holding it for several minutes, I was taken to the bathroom to expel it. After several minutes there, they took me back to the bed, where I was given another bag. While I was waiting for the cramps to require me to evacuate, I heard a sloshing sound next to me: I later learned my bedmate was being given a good pounding while he was full of water. That explained the plastic sheet covering the mattress.
After my bowels were emptied for the second time, one of my hosts turned me over on my back and took my virginity. He was gentle and I didn't feel the pain I was expecting. In fact, it was more than pleasant and I was rocking along with him. He was kind enough to take a picture of the event; I still have it (and it proves he was wearing a condom). While I was nervous about it initially, the experience was, overall, very good, if unconventional (I rarely have had conventional sensual adventures).
Keep in mind, when you write, that no two deflorations are the same. And, if you want to add a dose of reality, you may want to have your virgin concerned about hygiene and tearing.
Let us know when you've published your story. I'm looking forward to reading it.
saintcero
Literotica Guru
- Joined
- Sep 8, 2016
- Posts
- 4,499
Not my first time with a man but it was my first time to bottom. I had one oral experience a couple of years prior.
My
got popped at age 70. So happy to have completed that step of the journey. It was a special day and it left me wanting more. My Top was perfect. He seduced and prepared me until I was wanton. He was gentle at first but took his prize forcefully once my inner slut was triggered. We determined that we could safely bareback and so we did. I was given two loads and I treasured each one. I was plugged afterwards to keep his seed inside me. It was everything I had hoped it would be
He Fingered me. Rimmed me. Two fingers next. I begged him three times before he boned me. Over the sofa and then later again on a massage table, doggy and with my legs on his shoulders. And finally one last time in the shower as we cleaned up. I would have taken more but started to feel a little raw.
My
got popped at age 70. So happy to have completed that step of the journey. It was a special day and it left me wanting more. My Top was perfect. He seduced and prepared me until I was wanton. He was gentle at first but took his prize forcefully once my inner slut was triggered. We determined that we could safely bareback and so we did. I was given two loads and I treasured each one. I was plugged afterwards to keep his seed inside me. It was everything I had hoped it would be He Fingered me. Rimmed me. Two fingers next. I begged him three times before he boned me. Over the sofa and then later again on a massage table, doggy and with my legs on his shoulders. And finally one last time in the shower as we cleaned up. I would have taken more but started to feel a little raw.
