Brief history.I’m the quiet smart one of my parent’s 3 children and the oldest at 31, I went to university and dome well in all my subjects. My only failure was my social life, or more to the point love life, I didn’t have one at all. After university I got a job with the family company as was expected and rose quickly. According to my grandfather boss of the company, I was earmarked for higher positions due to my abilities. But I had to learn each area of the company first, so I was place in a section and once I had learnt it moved to the next section. Finally, I was made department manager (DM) and that is where my luck changed. The section was development section where we developed new products and improved older ones. Not any advanced gadgets, just simple everyday items that we made. I was the first DM the section had, having been a small group overseen by my grandfather. But as I’d done so well at university, he decided to enlarge the section into a whole department. Thus, moving from 5 staff to 20 staff, 4 times the size and I was to oversee and manage it. With 20 staff and me being required to oversee each project we were trying to improve or develop. I needed office staff and that was to be two, well one as my grandfather came me Shirley 49 from his own staff. To run my office and train the other woman. Shirley widowed and had a daughter Kerry 26 years and a granddaughter 2, the father of her granddaughter not hanging around after Kerry got pregnant. Shirley wanted to hire Kerry as the other woman. But I had to do the selecting, so Shirley had Kerry turn up for an interview before the job was advertised. I was distracted at the time and hadn’t realized the job wasn’t advertised at the interviewed. But Shirley plan didn’t take in one detail, my grandfather always said never take the first offering. I would’ve selected Kerry straight away otherwise, but with my grandfather’s saying ringing in my head I wanted to interview more women. That day after almost everybody was gone, Shirley made me an offer I couldn’t refuse, SEX. I had already said to Shirley, Kerry was suitable, but was going follow my grandfather’s saying and do more interviews first. So, Kerry already knew as it was common knowledge, I wasn’t great with women. Offered me sex in return for hiring her daughter. Shirley is okay looking and has a great figure, I was at first shocked. But soon was horny and agreed we fucked on my desk, and she promised me regular sex. So, Kerry got the job and was able to bring her daughter Suzie to work with her, she had a little area Suzie could play and be watched by her mother and grandmother. Once a week Shirley would stay back and fuck me. Kerry and I got on fairly well, my shyness around her lessening overtime. Finally, Shirley got the idea of me and Kerry dating, she asked me to ask Kerry out. I wasn’t keen on being rejected as was usual for me. But Shirley said Kerry likes you and would accept, I still wasn’t sure, and Shirley said she would ask Kerry if she would go out with me. The next day Shirley said Kerry would go out with me if I were to ask her. With Shirley beside me, I asked Kerry and she agreed to a date with me. Several dates and Shirley suggested I try to bed her daughter, as she reckoned, she would sleep with me. I wanted her to ask Kerry first, but she said it wasn’t a thing she could do and might put Kerry off sleeping with me. During a regular sex session after work, she got me to promise to try. So that following Friday night I was on a date with Kerry and made a move, an awkward move and Kerry spent the night with me. Of course, I was so stressed that I was clumsy and awkward and didn’t notice the condom slipping off as I was pulling it out fully and reinserting during the sex. I didn’t use condoms with Shirley, and it fell off and I left my sperm inside Kerry. Awkward, but she didn’t freakout as much as me. But taking her home in the morning, then telling Shirley. Shirley just said Well you better marry her straight away then. I took it as I had to marry Kerry and so asked to marry straight away. Both Kerry and Shirley thought I was playing along with Shirley teasing me about leaving my sperm inside Kerry. But I was serious, and Shirley realized first. So, she asked Kerry would she marry me, and Kerry I would if he was serious. Shirley than said he is and very serious, then Kerry suddenly realized it was a proper proposal. I was still in a bit shock over the whole marry idea, I was panicking a little for fear she might refuse. But she answered Yes, I’ll marry you (February 2022). I was very relieved and after staying a while I went to tell my family. They were happy and already knew Shirley and Kerry and were pleased. My grandmother gave me an old ring that had belonged to her mother and her mother before her. It was to be our engagement ring, I was dispatched to get Kerry, Suzie and Shirly. Kerry didn’t get pregnant from my first clumsy fuck with her, but there would be no repeats. As we didn’t use condoms after the engagement at all and still don’t. We were married April 2, 2022, fairly quickly as my grandmother made the arrangements and she doesn’t like long waits. Kerry got pregnant and we had our son in January 2024, Shirley shares our bed from time to time.
This story from Awkward Lover to Married man
has been read