At 25 Neil was a virgin. He'd never had a serious date with a girl. Even more unusual he'd never masturbated to orgasm. He'd tried... but he couldn't get hard no matter how much he touched himself. But almost every single night he woke with a rock hard cock spurting into his boxer shorts... and sometimes twice a night. But he could never remember his wet dreams.
After 5 years working on the other side of the country he was moving back to his hometown. His mother had moved into a one bedroom unit after he left so he couldn't stay with her while he found something permanent. So he called his best friend Karen.
Karen was keen to have him stay. She'd had fantasies about Neil for as long as she could remember. If he felt the same way then living in the same house just might get things started. If not, then she'd still be able to spend time with her best friend.
Her father and brother, Stuart, would be disappointed since either way they wouldn't be able to make their weekly visits to fuck her!
Karen had a few boyfriends after she turned 18 and had found them all to be very selfish lovers. Since then she'd enjoyed having daddy and Stu once a week each. Even they were fairly selfish... but they did at least satisfy her and didn't expect her to suck them off.
Neil arrived at Karen's place and they hugged. She showed him to the spare bedroom... hoping he wouldn't stay there long! Karen had only just arrived home when Neil had arrived so was still dressed in her starched white nurses uniform. Under it she had a white silky slip and matching panties. She was getting those wet and she imagined Neil licking her pussy!
Karen changed into one of her cute nighties but left her panties on. Normally she removed them when she got home but she didn't want to be to forward and had deliberately chosen a short nightie that would give Neil an excellent chance of peeking at her silky panties.
Neil was definitely very much in love with Karen... but the fact he'd never had an erection whilst awake left him doubting his ability to make love to her. So he enjoyed her company, and definitely enjoyed the peeks at her panties, but also didn't make a move. But he had three wet dreams that night.
Over the next 5 days he had 12 wet dreams. He realised being in her company was increasing his libido... but still couldn't bring himself to say anything.
Karen was getting worried that nothing would happen.
It was her day off so she headed into Neil's room and grabbed his washing. She sorted it carefully and was stunned at the dozen pairs of boxers that clearly had been creamed! Why would he masturbate in his boxers?
Another week passed. Still no move on her by Neil. But again 16 pairs of boxers that Neil had obviously cum into. Karen this time decided maybe she needed to make a move of sorts... she'd ask him about his underwear. She put them aside but did the rest of the washing.
Karen prepared a delicious dinner for them. She dressed in just pink Cottontails panties and a white nightie. Looking in the mirror she was pleased to see her panties showed clearly through the nightie.
Neil enjoyed the dinner and the way Karen was dressed, having no problem with the fact she was short and very plump. He was also a bit concerned though... all of his washing except for his boxers had been on his bed when he got home. The boxers, all of which he'd cum in were missing.
After dinner they sat in the lounge. Karen sat giving Neil a perfect view of her big panties. Then she dropped the bombshell question. "Neil, can I ask you a very personal question?"
Neil had nodded nervously.
"Why do you masturbate into your boxers?" Karen asked, emptying a bag containing all of his stained boxers onto the couch next to her.
Neil went bright red and couldn't find words.
"I'm happy for you to use one of the hand towels or some face washers if you would like Neil, it doesn't worry me! I'm a nurse so I've seen plenty... and often leave a patient with a towel for a few minutes!" Karen added.
Neil remained very red. "I wish I could do that Karen. If I tell you something do you promise not to tell any of our friends? It's very embarrassing but I suppose if I'm going to stay here I should explain."
Karen told him, "Of course! You should know that without asking. Whatever you tell me I promise to keep secret from all of our friends and families."
Neil then told her... "I've never masturbated to orgasm. I can't get hard when I play with myself. But every night I have a wet dream... and since I've been staying with you two or three a night. But I can never remember the dreams."
Karen was stunned but also intrigued. Looking at Neil she quickly stood and went and sat beside him and took him in her arms... Neil was crying. She settled him down and asked if he'd ever talked to a doctor about this. Neil told her he'd been too embarrassed and as yet hadn't.
Karen had an idea but didn't mention it yet to Neil.
That night she had another very good masturbation session thinking of Neil. The fact that he had multiple wet dreams since moving in with her gave her hope that something could still happen between them.
Next day Karen talked to Joanne, a phycologist, at the hospital. Joanne was also a friend... and occasionally lover. Joanne suggested a session of hypnotherapy. She also suggested that doing it in the home could be more successful as the patient would be more comfortable. "Will he need a referral?" Karen had asked, doubting Neil would be willing to get one.
Joanne had smiled. "Maybe we can make this just a off the record session. And the price... I'll need a damn good pussy licking from you! Ideally if he's up to it with him watching! I've always wanted to be watched!"
Karen had smiled. "Sounds wonderful! When?"
It was Thursday now and Karen was on afternoon shift today and tomorrow. They agreed that Joanne would come over at 9:00am on Saturday morning. "Most likely it's a fetish of some sort that Neil is suppressing. I'll get him to tell me his dreams and then work out the next step. If it's a dangerous fetish like rape fantasies I'll leave it repressed and then treat him in formal sessions. However if it's a harmless even though maybe embarrassing one I'll revel it for him and work with him to understand and accept it."
Karen asked, "Would it be possible for me to listen in?"
Joanne smiled, "I'll encourage Neil to let you do that... but it will be his decision. Make sure you wear something nice for me on Saturday! Hopefully Neil has a fetish that means he's happy to watch the two of us after his session!"
Saturday arrived! Karen showered then dressed in Joanne's favourite outfit. Exactly what Karen wore to work minus the uniform! White silky panties and a slip... and that was all. She walked into the kitchen where Neil was making the coffee. "Morning Neil, you don't mind if I wear just this do you?" Karen asked Neil.