So as mentioned, the combination of stress/pressure/horniess is making me do some weird weird weird (or is it my new normal?) things right now....
My stepdad's nephew came to visit for a couple of days (wished he would have stayed longer) to help take care of him and give me a break. This was good as he was able to take him out of the house, get a haircut, take him to prayer, etc. I'm hoping more of his family are starting to come visit/stay with us to help take care of him as it's tough to handle every day/night taking care of him.

While I had a couple of nights off ... I went ahead and contacted a professional dominatrix... I reached to a Domme who said they service people in my city. I was looking for Dommes in my area that seemed like they were good for newbies/rookies/virgins. I found this Domme (incredibly beautiful) who seemed like she was good for my level, also had a lot of my same interests. She was primarily based in another major city about 3 hours away but did sessions in my city.

I entered my bio/information/interests into their website and waited. Much to my shock, she actually replied back, and we exchanged some security questions/insight. We continued to talk back and forth more into details about myself/interests (this was on a Friday). She asked simple questions that I actually found really difficult to answer - why I'm so into chastity, sissy, bondage, etc. It helped me kind of understand myself a bit. This was really fun day as I was getting excited for the potential of meting with domme next week... However, Monday - no reply, Tuesday - no reply (I was starting to get worried as Friday/Saturday were my only days of free time). On Wednesday, I decided to contact her to see if we were still on for the scheduled but of course, she replied back a few hours later with "I'm still thinking about it" (welp).

Without hesitation, I decided that to look for another domme (I kept in mind that I was contacting someone with such a short notice of window - 2 or 3 days). I contacted a domme (post op trans woman) who seemed like a good fit and was based in my city. Within 1 hr, she replied back to me, and we exchanged information (I was very happy that she replied back to me within a short notice). Similarly, she asked questions about myself and wanted to know more about my kinks/fetishes. At the end, we agreed to meet for Friday for a 2 hr session back at her dungeon! I contacted the first Domme and made an excuse/called off the session (she was sure quick to respond then lol).

Thursday/ Friday - I had a lot of butterflies in my stomach, but thankfully my uncle was finally here and was taking the burden off from me. I kept messaging the domme about certain rules/protocols for us to meet. I also spent a lot of time preparing my body during this time - shaving my ass/penis, researching on anal diet/cleaning, playing with my dildo, did a lot of ass/leg exercises, etc (I had a feeling my ass would be a focal point during of session 😉). I decided that I was going to be wearing my chastity cage, my lacy panties, and a buttplug (this was the first time I would be wearing this combo in public). I packed a small bag with extra panties, vibrator, dildo, wipes, lube, and my chastity keys. We were meeting at a local coffee shop near her place for security purposes (understandable, but nervous as being in public).

I arrived at the coffee shop and order a drink to try to calm my nervous (this was stressful, which makes me pee a lot so that was fun). They coffee shop was half full and the only real space for us to sit was all the way near the counter (great). She was running bit late, but she arrived right around the time I came out of the bathroom. As a Tran Op woman, she def. looks great - she is much taller than me (I'm about 5'5", she's about 6 feet, she was wearing somewhat of a mini skirt, and a tight corset). It was def. noticeable who she was (she seems to frequent this coffee shop to meet new clients). It was funny, I was chatting with the barista as I waited, I talked about seeing her, when she came, he just gave me a me that look like "ah I get it now" lol.

We sat down and talked for a 5 min about our day, then she started to ask personal/kink questions which made me uncomfortable - so we went outside to chat (this might have been worse as the coffee shop was near a busy street/section). I saw a lot of people staring/looking at us which made me very uncomfortable, plus she was asking those personal questions lol - I just kept thinking fuck it, I'll hopefully never see these people in my life, and hopefully we won't have to come back to this coffee shop in the future. We spent about 25 min or so chatting, asking about my kinks/interest, how/why I wanted to be dominated by her, my hard limits, what to expect during our session, life in general - it was a good talk and gave me insight on myself. Finally, everything seemed good to go, and we decided to leave to go back to her place (thank god lol).

Her house wasn't too far away from the coffee shop (took about 15 min), but the area kind of seemed a bit sketchy, nevertheless, I found her place and entered her house (mind you see lives with 2 or 3 roommates who were at home at the time - added more anxiety/nervousness). As soon as I entered her dungeon, I was immediately ordered to strip naked. She had a small dungeon with various toys (primarily bondage/impact toys), riding bench, and X cross. She had a very devilish grin on her face when she saw my cage, panties, and butt plug - she made me pose a bit so she could take a good look at me. This was literally my first time getting naked in front of someone that wasn't at a medical exam/etc!

I was actually pretty calm during this time (idk how/why - I did take a blood pressure pill and some shots of vodka before our session, maybe that's why). The way she was commanding me and looking at me was like a tiger stalking its prey. My cage started to become very very very tight. She kept on asking me questions to get a better insight on how she would direct our session (this was a challenge for her because it was my first time & also, I'm a virgin - she didn't want to give a wrong/bad impression on either aspect). Might I add, she is very intelligent and gave great insight on everything - she certainly as a very dominant/confident aurora about herself, which was good because I felt other domes would be only playing a role to fit a need - she seemed genuine/honest.

She gave a quizzical look and started off our session by putting wrist and ankle cuffs on me and a strict posture collar on me (at this point there was no backing out of it). I was chained face towards the X cross with my ass exposed to her. It wasn't too tight as I have a bad shoulder, so she didn't make the chains too high up. During this whole time/entire process she kept asking questions and was very verbal/communicating on what she was going to do - which helped ease my anxiety. I should mention that she is a pure sadist - like blood/pain, which is a total hard limit for me lol, but she understood that and took that into consideration.

She started off by spanking my ass with her bare hands. She spent a solid 10 min spanking my ass and asking if I liked it (I really didn't like it, it just hurt a lot - the spanking pain wasn't registering into sexual pleasure for me). She decided to use a flogger on me, which she had to leave the dungeon and find it. It must have been 2 min, but during this time being naked and chained to the cross - I felt comfort/secure. She came back and started flogging with her toy, which started to feel better than using her hands. After a few min of spanking/flogging, she wanted to caress/grope my body - she told me as soon as I got naked that's that she wanted to fondle/molest my body. She wanted to know the feel of a virgin and wanted me to experience the first time of being manhandled and controlled.

I should mention that I think I have a pretty good ass and I have man boobs (about B size cups). She really really really loved caressing/groping/touching my ass and boobs. She would occasionally touch my balls/chastity cage which made me a jolt a bit. The way she would aggressively touch my body, made me body react in a very ticklish/responsive way - this made her giggle with excitement. She quickly found out (which I never knew) that my boobs/nipples were the most sensitive area on my body - the sensation traveled like electricity throughout my body. I became very soft spoken, my moans became a bit more desperate, and my breathing/sighs became heavier. (The only way I can describe how my body reacted to her hands is by porn reference lol - KINK.com Destruction of an Escort Chase, Scene 2 where Charlee Chase is tied in doggy position to the bed and Isis Love would touch/control her with her hands - the same way Charlee would react to her touches is the same way with me). As mentioned, I'm very small compared to her, she would put her entire body onto me while she molested me - I understood that I was so powerless and weak compared to her.

During this time/entire session she was verbally humiliation/saying positive affirmations to me, she kept on calling me a girl or referencing my dick as a clitty, what she was going to force me to do - here are some of my favorite phrases she said:
• "Good think your clitty is in a cage, it's not safe, it's too small to be free. Keep it soft/snuggled in your cage, so everyone knows who you really are".
• "What if I took your keys and never gave them back to you. What if the only way you will ever cum ever again is through anal only".
• "I wonder what all my friends would do with your ass, butt sluts are always the life of the party/orgy".
• "What if I kept you here as a slave, made your sissy transformation complete/permanent and pimped you out".
• "If you keep coming back to see me, I will make you more and more of a depraved slut".

Next, she started using a violent wand on me, which again like the spanking - felt more painful than pleasure. But it I did have some pleasant moments at times, especially when she would use it near my nipples. She had a setting on the violent want (low electricity setting) that felt like it was cutting/slicing my skin - she stopped after I told her I didn't like that lol. She then put 4 suction/coupling things on my back (on my sciatic nerve) which sucked on my skintight. It actually didn't hurt too bad; I could feel the sensations running through my nerves. She told me that they would leave some dark marks on my back which I didn't mind. After a while, she took them off and immediately started to lick/bite on the area. She would also bit on my upper back/shoulders and my ass - I felt I was getting eaten alive by a shark. She spent another 15 min using the violent wand on me, then went back to groping/caressing my body (I told you she really loved doing that). The pacing was going pretty smooth - not to fast/slow, not to painful/balanced pleasure.

She finally unchained me and told me to get on all 4s like a dog... I wonder why hmmm. I forgot to say that I was blindfolded the whole time. I could hear some toys coming out of her closet and gloves being put on. Suddenly I felt a firm grip on my buttplug as she slowly took it out. Again, she was giggling the whole time like a kid at a candy store. She slowly inserted a finger into my ass and started to play with it to make it loose. She was very informative about where my prostate/hemorrhoids (felt like I was getting a prostate exam). She then put another finger in my ass and was a bit more aggressive. When she started playing with my prostate - that felt strange. The way I would describe the sensation would be like having the urge to pee - it was a combination of frustration/alien to me (I pee a lot at night, the urge of peeing is a trigger for me, so I felt like I had to pee which I hated). As soon as she was playing with my prostate, I instinctually went face down, ass up, which was invited with laughter and some hard spankings. Apparently, my moans/breathing became much more lustful. Then she used a prostate massage/vibrator and put it inside me - woah this feeling was very weird. I started to drift into a therapeutic coma which I would awake from the occasionally spankings.

After a good while, it was time to bring on the strapon! But before that she, as I was still face down ass up, she asked me how I was feeling/what she was viewing. To be naked, in a slutty position, with your ass open ready to get pegged (this was very humiliating/exciting). She put on her strap on and slowly started to insert herself into me (I would say that the dildo was about 5-8 inches or so). The feeling of having a dildo in your ass was like being under a heavy blanket on a cold crisp night; it was comforting lol. She was slowly thrusting herself onto me, as I was trying to find a good rhythm to her. I truthfully felt like the strap on was small (I'm not lying I swear, maybe she opened me up/made me very loose). I shouldn't have said that to her, as she started to pick up the pace/aggression which I was desperately trying to match, but it just made me more and more vulnerable/submissive/accepting. She was in control the whole time but making sure that I was enjoying myself and not in any pain. She stopped for a bit and wanted me to ride her strap on and take control. This was humiliating/but fun as I fucked myself with her strap on - all I could hear was laughter and giggles (I guess I'm a natural buttslut). She fucked my ass for a solid 20 min or so. After a while she pulled out and I fell dead flat onto the ground exhausted. She told me to bring my ass up onto the air for one more thing (what else must I endure).

I felt a vibration sensation on my cage which made me wake up again. She was vibrating my cage with her vibrator; she told me the only way I would cum was in my cage with the vibrator or I wouldn't cum at all. She spent about 10 min using the vibrator which made me incredibly frustrated as I couldn't get enough of the sensation to bust. She stopped the vibrator which made moan very load in dissatisfaction (I think at this point her roommate could her me), but all that resulted was disappoint/laughter/and giggles from her.

Our session was pretty much up so she wanted to pause and discuss how our session went. In that moment it was very surreal - but I explained what I liked/didn't like etc. Overall, we spoke for a solid 20 min. which was very reflective/insightful on my experience. So, at last it was our night was over, I put back in my butt plug, put on my panties, put on my clothes, gave her a hug and I was off into the night!

Our session ended around 10 ish (we started a bit late), so I drove around the city buzzing/drunk off my experience. I decided to stop a 24-hour coffee shop to reward myself on another first accomplishment (of many wink wink). I rewarded myself with 4 butter rolls, 2 biscuits and gravy, a chopped steak with mashed potatoes and macaroni (I was fasting all day, so I was starving). I've already booked another session with her on the 24th, I will post another write up afterwards. There are some other things I would like to experience with her - crossdressing/feminization/sissification, more bondage, more pegging, possible femdom hand job/orgasm denial/control/ ruined orgasm, forced cum eating, possible forced bi play...

TLDR:
First session with a dominatrix (post trans op)
First time being tied up, spanked, groped, fingered, pegged
More insight on myself and why I like the kinks/fetishes that I do
2nd session already booked!