Written by Flagg

15 Oct 2013


A couple of months after Sam and I started dating, I received a telephone call from her mother, Mrs Smith, one afternoon. She was brief to the point of curtness – her request that I should go over to their house as there was something that she wanted to discuss with me.

O shit! I knew that this meant trouble. Sam wasn’t there for the week. She was away on a school camp. I knew that the only thing that Mrs Smith could possibly want to discuss with me was my relationship with her daughter. Did she suspect that we were doing a little bit more than merely kissing?

Later that afternoon, I arrived at their home with a heavy heart. When Mrs Smith opened the door, it was difficult for me to judge her expression. As always, however, she was impeccably dressed in a black pencil skirt and white button down blouse. She invited me in and escorted me to the patio next to the pool. She asked if I wanted to drink anything, and when I said that I didn’t, she left to fetch herself a glass of wine. When she came back, she invited me to sit down and started making small talk.

It wasn’t long, however, before she got to the point. ‘You have been dating Samantha now for about 3 months’ she said. ‘Yes Mrs Smith’ I replied. ‘Are you serious about her?’ she continued. ‘Yes of course Mrs Smith’ I replied. ‘Good. Here’s the thing though… I know what the two of you have been getting up to.’ Deciding to play it dumb, I replied ‘What do you mean, Mrs Smith?’ ‘I saw what you were doing the other day in the pool’ she said. ‘The pool?’ I asked. ‘Don’t play dumb with me young mister. From the look on Samantha’s face it was obvious what was going on. And, when you turned around to greet me, the tip of your erect penis was clearly visible to me. I didn’t say anything then because I didn’t want to embarrass you by having to stand up and face me before my daughter with your erection poking through the zip of your pants. Do you have anything to say for yourself?’

I didn’t know what to do. I just sat there blushing and looking at the ground. ‘Look me in the eye, Mrs Smith said. ‘There is only one way out of this for you.’ Taking a sip of her wine, she continued, ‘I’m going to get up now and go inside for ten minutes. You have to decide whether you are going to stay or go. Here’s the catch - If you decide to leave, I will not allow you to continue dating my daughter. If you decide to stay, you will take off all your clothes. When I come back out, you will stand next to that chair with an erect penis. Understand?’ With that, she got up and went inside.

For a while, I just sat there, completely flabbergasted. I didn’t know what to think or do. Was she serious, or was this some kind of sick joke? What if I did decide to stay and take off my clothes and it was all a trap? What if Mr Smith came back and walked in on me standing naked on his patio? After a while, however, I realised that I didn’t really have any choice in the matter at all. I wanted to continue seeing Sam, and that meant that I had to do as instructed.

I got up and slowly started getting undressed – my shirt first, and then my shoes, pants and underpants. Then the difficult part – up until then I wasn’t aware of how difficult it was to ‘perform’ when in a stressful situation and forced to do so. My cock was flaccid and my time was running out. I knew that Mrs Smith would be coming back out any minute now and that I would be in trouble if I couldn’t get my dick up. With some vigorous rubbing and jerking, I managed to start getting some life into it, and after rubbing some spit on my palm and more serious jerking I got my cock to stand up stiff – fully erect. I still didn’t know whether all of this was a joke though, but decided that I was in for it in any event, and just had to go through with it.

While standing there waiting, I kept on stroking my cock. If I think back, this must have served two purposes. Although it ensured that I kept my cock fully erect, it also kept my nerves at bay. With that Mrs Smith walked back out. My first reaction was to stop stroking myself, and to try to cover my erection with my two hands. Mrs Smith’s reaction was completely unexpected, however. Without blinking an eye at the fact that I was standing there naked, she sat down in the chair next to me, took a sip of her wine, and said, ‘You decided to stay and do as I requested. Good for you. Now come stand next to my chair and take those hands away. Keep them behind your back.’ With that, I placed my hands behind my back and walked closer to her chair. ‘I said closer – stand right here with your legs up against the armrest of my chair.’ Once again, I complied, standing right up against the chair, with my balls dangling over the armrest and my cock basically on level with Mrs Smith’s breasts and mere inches away from her face. Her only comment while she was examining my stiff penis from up close was, ‘Okay, that better…’ For once, I did not receive any comments on the unusual shape of my thick cock-head or the fact that my shaft angled to the left. While Mrs Smith continued studying every detail of my erection, she continued, ‘Now I want you to twitch your penis, you know, contract your muscles.’ Again, I did as instructed, resulting in my cock bobbing from side to side, with my cock-head occasionally slapping against my stomach.

Strangely enough, I was starting to lose the nervousness that I initially had. In a weird fashion, I was starting to enjoy this, even finding it highly erotic. To be honest, looking down at Mrs Smith (still very attractive despite her age) sitting there fully dressed while inspecting every inch of my naked cock was getting me extremely horny! Mrs Smith then commanded me to start, in her words, ‘masturbating your big muscle’. Without hesitation, I gripped my shaft and started to rub it, my foreskin moving backwards and forwards behind my cock-head. As the tempo increased, I lubricated my head by spreading the pre-cum starting to escape over it. While this was going on, I closed my eyes and started to fantasise about Sam’s naked body – images of her beautiful big breasts and long pussy lips whirling through my mind. At one point, however, I caught myself imagining what Mrs Smith would look like without her clothes on…

As I was starting to move towards a climax, I guess clearly evident from my facial expression and the speed at which I was jerking my cock, Mrs Smith spoke up, ‘When you are ready, I want you to ejaculate over my face.’ That was all that she said, and although I was a bit taken aback by it, I decided to rather do as asked. It wasn’t long thereafter that I stared spraying her face with jets of cum. She just sat there taking it all, from the first jet that hit her forehead and trailed down over her right eye, nose and mouth, to the subsequent ones that covered her chin, with some of it ending up on her blouse and skirt.

As I was finishing off, Mrs Smith spoke again, ‘You can rub the remaining semen from your penis with my hair.’ I realised that she had not touched me once during this whole incident. Again, I did as I was told, and wrapped my cock in her long curly brown hair and wiped the remaining cum off my dick, before stepping back from the chair.

Mrs Smith continued to sit there looking at me with her cum covered face. She didn’t do anything to wipe it away, and as she reached over, picked up her glass and took a sip of her wine, I saw a glob of my semen trail down her chin and drop into the cleavage of her blouse. ‘Okay, that is all for now, you may get dressed and let yourself out.’ Just like that. I stood staring at her for a while longer, before turning around and putting my clothes back on. As I walked to the patio door, she called me to attention again, ‘I trust that you will keep this little encounter to yourself?’ The last sight that I had of her that day before turning to leave was Mrs Smith sticking out her tongue and licking some of my semen from her chin.