I had been wearing bra and thong in secret for several years; my wife was unaware of this thankfully. I had been chatting with guys on a dating / hook up site and had had a few meets but not truly what I had been hoping for.
I signed in to find a message from an older gent who lived a little further than I was normally willing to drive. I checked out his profile, good looking, couple years older than me, nice looking cock and decent body, no face picture.
His message was: Hi Sophie, nice profile, you look good in the pictures, and I am sure even better in person. While you seem to have had a few flings would you be interested in something perhaps a little more serious?
This started an email conversation which I will briefly highlight below. P-Peter S-Sophie (me)
S- Serious? Like what do you mean
P-perhaps an ongoing situation..meet up 1-2 a month, when you can get away from your wife, if that is possible. Let me help you become more girly and submissive, be my kinky little sissy girlfriend.
S- Well I can get away from my wife once or twice a month with no real problem. I just have to let you know a few things, bit embarrassing but hey. I have an enlarged prostrate and am on meds which make it hard to get a hard erection and also make me super tight and hard to be fucked, in fact it has been many years since I had a cock inside me.
P- Thank you Sophie for letting me know about your medical issue, thankfully I am not really looking for you to get hard, after all you will be my girlfriend, I am not interested in sucking you or being fucked, I am a total top after all, I just want your body and mind to be my sissy. I want you to be girly around me, let me kiss you, make out with you, play with your body using toys and get kinky with you. What do you think Babygirl?
S- Wel you certainly have got me intrigued for sure, lol, what kinks you have in mind? Sophie xxxx
P- Hey Babygirl, sorry it took so long to get back to you. Well kinks I like are golden showers / water sports, I love using dildos, butt plugs, nipple clamps, spanking, maybe down the road doing some live streaming, keeping your face hidden of course. I would also like to be able to introduce you to some of my friends who like me appreciate someone like you. I know we are a little further away than you have said you are normally ok with, so perhaps we could meet mid-way at a hotel and see if there is any magic between us. I can get the room and when you arrive, we can split the cost. When you arrive text me and I can come down and meet you. Let me know what you think Sissy Sophie. Hugs and kisses Daddy.
S- Hi Daddy, yeah I think I can do that, free in a couple weeks..midweek ok? Sissy Sophie xxx
We chatted more than this naturally.
We set our meet for Tuesday afternoon 3pm, 2 double beds in an inexpensive hotel, one where they didn’t may to much attention to the coming and goings, and close to a few pubs and restaurants.
I drove down just over 2 hrs, had on cargo trousers and a polo with socks and trainers, and a pink thong, my overnight back with lingerie etc in the seat next to me. My mind raced with different thoughts from was I going to get hurt to how kinky it would be my stomach had butterflies from nerves and excitement. When I arrived and parked it took me 20 minutes before, I took a deep breath, calmed down a little and texted him that I had arrived. Grabbing my bag I stepped out, locked the car and walked towards the entrance. He texted back he was waiting just off the lobby.
Peter was 6ft, shirt and dress trousers, black shoes, little bit of a belly on him, slightly balding and with a huge smile. I couldn’t help but smile back as I walked towards him.
I wasn’t sure if I should shake his hand or give him a friendly hug, thankfully Peter took care of that and gave me a friendly hug, pat on the back as his whispered softly “Hi my little sissy Sophie.” My heart did flutter a bit. “Let’s grab a coffee” he said. We sat down opposite each other as we waited for the coffees to arrive, ideal banter..how was the trip down etc. Coffees arrived and we continued to chat, loved our conversations, so glad you could make it, innocent to others but filled with erotism for us.
Peter smiled, “ I think we should head to the room now, I can’t wait to get a more intimate look at you.” He said with chuckle. We got up and I grabbed my bag and we headed down the hallway to his room. We didn’t say a word till we arrived and he unlocked the door, “ladies first “ he said.
It was your standard type room, beds, TV etc, Peter had his laptop on the table, there were some dildos and lube and a couple of little bags on the drawers next to the TV. I put my bag down against the chest of drawers as Peter moved past me.
He sat on the edge of one of the beds, “So Sophie, here we are after all our chats, face to face, how you feeling?” I had promised to be honest with him during our chats. I replied I was excited and nervous, giggled and said more excited to be honest.
Well that’s a good thing, I am very excited to see you, so are you ready to put yourself in my hands? He said firmly. I nodded and softly said Yes, Daddy.
Good girl he said, now why don’t you strip down and let me see what we have to work with, after all the pictures aren’t gonna be the same as seeing you in the flesh.
He watched me slip my trainers off, sliding them next to the wall, balancing on one foot at a time I took off my socks, exposing my pink painted toe nails. I took off my watch and emptied my pockets, phone, keys and wallet and undid my belt. I pulled off my polo shirt and stepped out of my trousers, standing in my pink thong blushing hard.
Now slowly spin around he said.
He had me pause for a few secs as my ass faced him, when I was back facing him he was still thankfully smiling.
You did a great job shaving like I told you he said, very sexy and very feminine figure you have he said. I blushed and let out a little giggle. Nice touch wearing the thong and painting your toe nails. Seems like you are eager to please Daddy aren’t you, I nodded yes.
You feel good about showing your sissy side to me, huh, I nodded and said yes.
You can do better than that he said, tell me.
I paused …Daddy it feels so very good to be standing here letting you see my sissy side. I started to say something but stopped. My brain screamed at me….Yes let your sissy side out, be free, I felt a couple of waves of warmth rush over me, I even felt my eyes fill up a little.
Nice Sophie he said, but it seemed you started to say something else and stopped. He stood up and stepped close to me, his hands ran up and down my shoulders and arms. I could feel his warm breath. Remember being my girl is not just about the physical body but also about your thoughts and feelings. Let go be yourself, you are safe here. He kissed my forehead.
It is just silly I said, he stroked my face…so? What was it?
After a little more encouragement I said..Just a lot of emotions and excitement about this whole thing, excited to be able to be your sissy and be a girl, is kinda overwhelming.
He hugged me tight, we will have a fun and exciting journey together he said and stepped back, letting me go.
He looked at his watch, well we have some time before dinner, we should get you into the shower and help finish the job you did shaving and clean out your pussy then suck me off before we go out and grab a bite to eat, I smiled and said sure thing.
I got us a handicap accessible room so the bathroom is bigger he said as he took my hand in his pulling me towards the bathroom. It was in fact bigger. He had laid out several razors and shaving cream on the sink along side an enema kit. As he started to run the water he turned, why don’t you put on your wig. I nodded and went back outside and into my bag and pulled out my blonde shoulder length wig and put it on, I adjusted my ponytail making it snug and walked back into the bathroom.
Such a sexy sissy Sophie he said, hop on in. I slipped off my thong and stepped into the shower. Perfect temp. Soon he took the shower head down and let me cover myself with shaving foam and watched me shave, I was pretty smooth already from my shower and shave that morning. I knew he was getting hard watching me. I kinda got off trying to be sexy for him. Once I was done he told me to get on all four, pussy in the air.
I felt his hand rub some lube over my hole, his finger pushing gently against me. He playfully smack my ass cheek, “you weren’t kidding, you have a super tight little cunt, be fun to loosen you up” I felt the nozzle push against and slip inside me and the warm water fill up inside me. I moaned and groaned softly, it felt really good.
He repeated the process a few times before smacking my ass playfull and said all done, dry off.
I got up and stepped out and started to dry off, Peter was in the other room, my wig was dripping and I had to hang it up. When I walked back naked into the main room Peter had my trousers and polo shirt over the chair in the room along with my sock and shoes under the chair. On the bed was a small butt plug, lube, bra and thong and nipple clamps. He had me put on the bra and thong then kneel on the bed as he clipped on the nipple clamps and slipped the bra back over them. The he had me on all fours and with some lube and a little effort accompanied by a yelp from me, pushed the butt plug inside me. I had to take a few gasps, was a little sore going in. As I turned around on all fours on the bed to face Peter he was standing right next to the edge of the bed, I could see he was getting hard.
Sophie ready for her creamy appetizer, I nodded, I had been dying to see his uncut cock in real life, it had look big and nice in his pics. I undid his belt and zipper, he let his trousers fall down to his knees, I reach around his waist and eagerly pulled down his boxers, I was face to face with a thick, growing uncut cock. I took it in my mouth and started to suck, it quickly grew hard with my sucking. Gently pulling back his foreskin I licked his big mushroom head. I was not a mouthful but very close. I tried to take him balls deep as I sucked, but my gag reflex hit and I could only take about 6 inches, leaving the remain 2 inches, I figured he was a good 8 inches. As I sucked Peter rested his hands on my head and on my shoulders as he slowly began to thrust as I sucked. Don’t worry he said I will warn you before I cum, I know you aren’t too keen on swallowing, so a nice facial will do.
As I sucked he started to say nice things about me, sexy, hot etc, teasing me a little about being a sissy, I could tell he was getting close to cumming, I didn’t care I was in heaven sucking his cock. He let out a big groan and grunt gonna cum he said, I pushed down on his cock as I felt the first pulse of his cock squirt cum into my throat, 3, 4 5 pulses each followed by a squirt of cum, as he sighed and pulled out of my mouth I continued to lick the last drops of cum. Fuck he said that was awesome, I didn’t think you were gonna let me cum in your mouth, what happened. I chuckled …felt right I said. H helped me up off the bed, get dressed lets grab some food.
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