Annabelle

(6 foot 5 tall and lanky ginger nerd girl with glasses and braces, just turned 18 today and she is studying medical sciences specifically biology, more specifically male penises, complete virgin and shy but excited for her first time and very intrigued to study anything penis related. wants a man of her own for research and love making purposes.)

Jack read threw all of the profiles Kelly had made for him, by this stage his period was making him feel so needy he didn't care who it was but he had to pick he couldn't wait any longer he needed to send the message no mater who he chose.

'Kelly I think maybe I should try Annabelle? I mean I guess she is maybe a bit more shy and less cocky so she might get on with me better plus gingers are pretty not that I seen her or anything I just assume. Kelly do you think she would be monogamous? do you think she would want to marry me or like whatever the equivalent of that is. from your description she seems like she would at least take an interest in me and how I am right now but what do you think Kelly like is she a good option for me?'

........

'Omg yes Jackie I think she would be perfect for a first timer like you maybe even too perfect for what you want I mean the girl is a nerd, she isn't likely to gain any courage or ego like that, girl could barely catch a man if she tried well I mean unless one got to close to her vag I mean but I think even she would be to timid to let a man do that to himself or her impose herself on a guy. Girl is training to be a frigging penis doctor so hope that doesn't matter to much to you but I bet even if she gets to look at peens all day the only one that would ever end up inside her would be yours, at least she will be well versed in all things sissy dick you know pleasure spots, periods, pregnancy etc like if you dated she could give you free pregnancy consultation or penile check-ups and you wouldn't even have to leave home. plus I bet she is in student housing right now anyways being that she is a student so shed probably be thrilled to find a guy a little older who lets her stay in his room and does chores for her all for the low price of her romantic loyalty, love and affection oh and lots of her fertile semen.'

Upon reading the word semen jacks penis jumped up as if somehow knew had made a good decision or at least a decision which was a good thing as his rather controlling period hormones and what not got closer to their sexual goals.

'sounds good Kelly, I'm really starting to get super horny right now, just thinking about a woman makes me need one, I wanna fuck so bad and its so strange cos my penis aches and stings and it feels like I'm peeing blood but like all I can do to help it right now is watch porn and play with my cock whilst it drains. But it wants something else, it wants to drink cum from a pussy I don't really get how, why, I haven't done it before. Maybe all my body wants even this virgin girls pussy, I hope she makes a whole bunch I need it inside me, oh my I cant control myself why am I saying these things , why am I thinking this , I should be horrified by this , Kelly why am I not disgusted by this reality what am I becoming.'

......

'Jack your a man, a sissy male, its normal especially if you got a high level male estrogen production and heavy period. no one is judging you for your urges, and I'm sure Annabelle wont either, girl is going to be ecstatic she got the draft in from the short list and even more excited when she realises she gets to keep you to herself forever assuming you want the equivalent to marriage, I'm gunna pick her up and bring her home this evening with all her stuff , I don't mind another woman living with us I guess, it will be a win win for her so I bet she instantly moves out of her whatever she has and into your room, prepare your self for all her stuff oh and prepare yourself for tonight cos girl is gunna be up all night "experimenting" or "researching" your penis xD. You know how nerds can get especially ones who are getting their hands on the genitals of the opposite sex for the first time, i mean look at you only knew about this girl less than 10 minutes ago and now you already want to fuck without even meeting her.'

Jack put his phone down in relief, he'd secured a woman most likely for life and she would want him for him, even if it was a bit clingy or clinical. Hopefully she treated him like a person and not like a project all the time but it didn't matter at this point he'd be up all night getting lucky and making his body feel amazing especially if she had a level of understanding oof male bodies higher than that of a regular woman. she could make him have a proper orgasm and if it was anything like his current orgasm he was experiencing from his toy inside him now he'd be pleased but the reality was this was just a toy and the real deal would be infinitely better.

He thought about this mystery girl in his mind, he didn't know much about her other than what Kelly's profile had told him. tall skinny maybe a bit weaker for a girl and nerdy. not a woman of bravado but a woman of logic, reason and learning perhaps. perhaps she might not be the most dominant at first but maybe that would be a good thing, he wasn't from this world originally so maybe a dominant lady might have been to much of a culture change for jack. None the less the thought of a woman wanting him for sex or to be her sexual science partner was growing on him moment by moment to the point he'd accepted he was fully focused on this path in life and he wanted to be the best sissy husband for her he possibly could.

Jack finished his thoughts and orgasm after a while realising the time had pasted way quicker than he was expecting, it was almost evening now and Kelly would almost be here with this Annabelle girl, the thought had dawned on jack that if her 18th birthday was today then she would barely be a woman and well he'd probably be making her a woman tonight probably taking her first time and her his.
Jack barely had time to remove himself from the toys he had been using and go find something to wear, inserting a new tampon into his penis before finding some nice sexy tight red panties and a matching bralette, his best looking casual pink dress and touching up his makeup. He heard the front door downstairs open and noises in the kitchen, things being moved around and women talking, then smells of something nice? was Kelly cooking dinner, jack would have to go investigate, hopefully he was presentable enough at the least or hopefully attractive enough looking to immediately hit it off with this young lady.

He went downstairs to find