Mistress and I went on a week long trip to somewhere tropical. Last Saturday morning Mistress let me out of chastity for our vacation. I packed my teeny tiny device just in case.
The first hotel we had was a very nice place. On the first night I gave Mistress several orgasms and had to beg her to not make me cum. It was then that I had agreed to wear a nighty every night for the rest of my life and to keep my fingernails and toenails painted for the rest of my life. Mistress said I had to keep them nice as well, no slacking. I am looking forward to other life long D/s enhancements to our life. After we went to bed, I locked myself up as I was so horny and I didn't want the temptation.
The next morning I went up to the private patio on the roof. I wish I had known our room had this as I would have brought my bikini bottoms. Instead I improvised with a pair of thong underwear and did some private sunbathing. I am getting a nice feminine bikini style tan.
The rest of the trip I did my best to try and get Mistress to let me pleasure her, but she kept me wanting and extremely horny. I wore a nighty every night which also kept my horniness at a level 10.
One night we were out for dinner after a few too many drinks. There was an attractive woman that was waiting for a table and she was standing behind me. Mistress is ok with me checking out other women, but apparently I over did it this time, although it didn't feel that way. We got in a bit of a tiff. I wished I didn't get so defensive. I need to be punished for gawking and for getting defensive. In the future, I'd also like to have a protocol where Mistress says something likes "eyes down" or "eyes, front and center" as a command to stop gawking. She would practice it in public on a regular basis to make sure I don't hesitate and I don't react poorly.
Yesterday Mistress and I were hanging out in a small private-ish plunge pool. We started making out and I was telling her how I needed to buy her another gift so that I can get another torture session. I rubbed her clit through her bating suit and she rubbed my cock. In short order, my swimsuit was unzipped and Mistress had full access to my cock. She stroked me all while I begged her to get meaner and meaner with me. I hinted we needed to pull out the fucking machine as well as the sucking machine. I was soooo horny. In no time at all I was on the edge of cumming and asked Mistress if I could cum. I had hoped she would say no and would stop stroking me, but instead Mistress made me spew a month's worth of cum into the pool. I was shocked and spent all at the same time.
I would have thought the orgasm would have reduced my horniness and my desire to be tortured, but it only amplified it. I did have a tough time this morning. Typically on vacation I would have sneaked off and given myself another orgasm, but I stayed true and did not.
As I sit in the airport and type this I am reminded of a conversation we had before bed last night. Mistress said she wanted to buy me some more chastity friendly underwear. I am guessing I will be locked up sooner rather than later. I love my Mistress and how she brings out my desperation.
The first hotel we had was a very nice place. On the first night I gave Mistress several orgasms and had to beg her to not make me cum. It was then that I had agreed to wear a nighty every night for the rest of my life and to keep my fingernails and toenails painted for the rest of my life. Mistress said I had to keep them nice as well, no slacking. I am looking forward to other life long D/s enhancements to our life. After we went to bed, I locked myself up as I was so horny and I didn't want the temptation.
The next morning I went up to the private patio on the roof. I wish I had known our room had this as I would have brought my bikini bottoms. Instead I improvised with a pair of thong underwear and did some private sunbathing. I am getting a nice feminine bikini style tan.
The rest of the trip I did my best to try and get Mistress to let me pleasure her, but she kept me wanting and extremely horny. I wore a nighty every night which also kept my horniness at a level 10.
One night we were out for dinner after a few too many drinks. There was an attractive woman that was waiting for a table and she was standing behind me. Mistress is ok with me checking out other women, but apparently I over did it this time, although it didn't feel that way. We got in a bit of a tiff. I wished I didn't get so defensive. I need to be punished for gawking and for getting defensive. In the future, I'd also like to have a protocol where Mistress says something likes "eyes down" or "eyes, front and center" as a command to stop gawking. She would practice it in public on a regular basis to make sure I don't hesitate and I don't react poorly.
Yesterday Mistress and I were hanging out in a small private-ish plunge pool. We started making out and I was telling her how I needed to buy her another gift so that I can get another torture session. I rubbed her clit through her bating suit and she rubbed my cock. In short order, my swimsuit was unzipped and Mistress had full access to my cock. She stroked me all while I begged her to get meaner and meaner with me. I hinted we needed to pull out the fucking machine as well as the sucking machine. I was soooo horny. In no time at all I was on the edge of cumming and asked Mistress if I could cum. I had hoped she would say no and would stop stroking me, but instead Mistress made me spew a month's worth of cum into the pool. I was shocked and spent all at the same time.
I would have thought the orgasm would have reduced my horniness and my desire to be tortured, but it only amplified it. I did have a tough time this morning. Typically on vacation I would have sneaked off and given myself another orgasm, but I stayed true and did not.
As I sit in the airport and type this I am reminded of a conversation we had before bed last night. Mistress said she wanted to buy me some more chastity friendly underwear. I am guessing I will be locked up sooner rather than later. I love my Mistress and how she brings out my desperation.