Searching for a sissy

Not that it matters but I find the reasoning and motivation behind his want/need for a sissy to take his virginity kind of odd. I believe there is someone for everyone out there and if he really wanted to I’m sure he could find a woman if he was really motivated. I would think that this is more of a driven fantasy of having sex with a sissy versus being what he believes to be his last and only option. By no means am I judging and honestly I hope this does happen because I want to hear about it lol. But the reasoning behind it seems kind of odd to me . He probably doesn’t want someone who quite a bit older than him but at this rate he shouldn’t be picky, as the saying beggars can’t be choosers applies here. He should be set up with “Paula” she’d probably rock his world lol.

 

I think this is more of a case of polluting his mind with transsexual porn and this is what he thinks he wants...

 

I did a search on fab

TS/TS/CDs, age 20 to 30
Who want to meet a man
(have public photos)
Within 5 miles of birmingham

got about 106 profiles some are super cute. some are amazing!

maybe he's building up the first time too much? if he told people he was a virgin it'd probably take the pressure off.

this lady is in birmingham

 

@L-u-c-y
I think if he just goes to have sex he’s going to be disappointed in it other than him being able to say he’s not a virgin anymore, which doesn’t really mean anything unless you’re trying to impress a bunch of teenage boys. One of my friends from high school lost his virginity to a girl who was open to ANYONE at the party. He had been getting a lot of flak for being a virgin from one of our other friends who’s a total alpha. I’m sure our friend plus other societal pressures pushed him into having sex with this woman which he ended up regretting and feeling really dirty and embarrassed afterwards. He wasn’t the first she’d had that night either.

It wouldn’t be a bad idea to require him/advise him to maybe establish somewhat of an emotional connection/relationship with the sissy before they just take to the bedroom. Have him take the sissy on a couple of dates, let them get a few make out sessions in. Maybe even have the sissy hold his key until the sissy says yes to sex (which probably wouldn’t take long). It would probably be good for him to have to work for it a little more.

If it just happens straight away it’ll probably only last a few minutes and both parties will more than likely be disappointed in the end result. If they establish a connection/relationship both might want to get together more often versus just one night of possible confusion and embarrassment. I also agree with @Sthsde_cd that he should admit to being a virgin, it’ll toally take the pressure off. I also think him being a virgin might be a good reason for him to find a more “seasoned” sissy that can guide him and make him feel more at ease so maybe tack another 5 or so years onto that age range to cultivate more options.

 

Wow - she suddenly made me feel like being a virgin in Birmingham!

 

I am 24 year old Virgin do I need to start looking for Sissy next year then?

 

I feel like anybody could be forced into becoming a sissy via chastity

 

I would be interested but I'm too far away. If he's your slave, it would be my pleasure to serve him too

 

I remember my first time I had some back and forth with a CD in Sydney Australia. Her pictures looked nice and I turned up her apartment. I was somewhat disappointed she was not a hot as her pictures initially but was too far to pull back. After a little time chat and intimate time on sofa she took me to bed. I walked out somewhat in shock as I had only been with real girls before. But after some reflection I realised I enjoyed it and never looked back

 

I must admit to being just a little disappointed. For just a moment I thought @L-u-c-y was looking for a sissy of her own. I'm still curious to see where this goes.

 

Did thus ever work out?

 

He will feel like a real man after talking to me, im v inadequate and sissy for him to control