Regrets for a Miss

by Clansman


Romantic Sex Story: A man and woman meet and a courtship begins but as the tittle suggests it is not all plain sailing. Does it lead to happiness and fulfilment or sadness and loss. The idea was sparked by an email from one of my female readers. So this is for carol Anne. Some sex

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   .

My Name is Robbie McLean. I was the new kid on the block as far as the sales team in our company went, but already I was nearing the top of the rankings. It is not something I boast about but I find sales easy. I think it's partly to do with my genes. My dad is one of those kind of guys who can get along with everybody. He always has Joke. He is the one in the doctor's surgery who will break the ice and have everybody talking to one another within five minutes. Over and above that he is always helpful and a really nice person. I think I have one advantage over him. I also inherited my mother's good looks without being effeminate.

So with her looks and my dad's easy charm I can woo the birds off the trees. So you see why sales come kind of easy. People are pleased to see me and within a few minutes we are chatting like old friends. It sure helps when it comes to closing a deal on a sales pitch and almost always makes a return order a near certainty. It doesn't do any harm when it comes to women either. I do quite well on that front as you can imagine. If there is a drawback, it is in the fact that like my dad I am quite a nice guy, so I don't want to exploit or hurt people so I don't shoot lines just to get sex.

I'm telling you all this because in our office the one we report to and the one who passes on messages from the boss, is Carol Anne. She is a wow, beautifully coiffured dark hair, twinkling eyes, and a ready sense of humour and a great smile. Her figure doesn't hurt either, long slender and shapely legs, an arse to die for, trim at the waist and her c cup breast fit her body perfectly.

Of course dealing with a sales team she had become immune to their glib attempts to woo her out of her knickers and handles their passes with tact, diplomacy and humour. She always leaves them thinking that she likes them and maybe next time ... Well you know what I mean.

Just Like the rest of the guys I would have loved to get her into bed, and I humorously made attempts to get her to go out with me but at the same time letting her know I did not expect she would. I don't know what changed her mind, but one day when I was making my usual sales pitch for a date, she didn't respond instantly but looked at me thoughtfully and then she said,

"Ok, where are you proposing to take me?"

I was flabbergasted and it took me a moment to respond then I suggested, "How about dinner and a movie?"

She still lived with her parents, so I agreed to pick her up at their place. The traffic on the way to her house was lighter than I expected so I was a bit early when I knocked on her door. Her Father opened it and when he saw me a smile lit up his face,

"Come on in Son," he said, "Carole Anne is probably putting the finishing touches to her makeup."

We chatted easily and I learned that he was a great soccer fan and a church elder. His wife told me that they were really pleased that their daughter had decided to start dating again I learned that she had been engaged to a guy for two years and then he ditched her for some bimbo. Since then she had shied away from any kind of commitment.

When she came down the stairs my heart nearly stopped and I could feel Robbie Junior getting hard in my pants. She was a wet dream walking. However, I managed to hide my state of arousal and went towards her and took her hand and said,

"Carole Anne you are absolutely stunning, I am not going to be able to take my eyes of you all night."

I gave her a light kiss on the cheek and she gave that lovely musical laugh that she had and quipped,

"Not a bad sales pitch Robbie, but I bet you say that to all your dates."

I smiled at her and replied,

"Of course I do, but this time I really mean it."

Her father laughed, and her mother said with a smile,

"I would watch this one, Carol Anne. He's a real sweet talker, just like your dad and look where that has landed me."

I smiled over at her and said,

"You don't look as if you are all that depressed about it, and if your figure and looks are anything to go by I think Carol Anne would be a great prospect for the long term."

Her mother and father both laughed at this and her mother said,

"That confirms it, a real sweet talking guy who has just managed to compliment both of us at one go"

Carol Anne and I joined in her parents' laughter. A real nice family I thought and judging by their concern for their daughter, a real close one too.

The date went really well and we shared a lot of the same interests. She was into fantasy writers and as a Scot I was a great David Gemmel fan, I liked the Hobbit, Lord of the Rings, J.V. Jones and others. We got so engrossed in our conversation over dinner that we never made it to the movies.

So we ended our date by parking for a while. We kissed a bit and talked a bit more. As I parked by her gate, I told her I had a really good time and would like to do it again. She agreed. I was away on a sales trip for the rest of that week, so I made a date for the Saturday night. She liked to go dancing and as an exiled Scot in England I was a member of the local Scottish society and it was holding a Ceilidh that night and I suggested we go there.

Their dances were a mixture of Scottish reels, and Jigs, barn dances and what we called old time dancing. She had never done anything like that but she agreed to go. If you have never been to a Ceilidh (pronounced Kaley) then you will not be aware that it requires a great deal of energy to dance every dance. Dances like the eightsome reel and strip the willow and one or two others leave you exhausted at the end of them.

Once Carol Anne got into the swing of things, if it had not been that one or two others were keen to dance with her, I would have been worn to a frazzle. But when the others took the floor with her, I got time to catch my breath and watch her hooch and holler with the best of them. It was after midnight when the dance finished and when we arrived back at her house, all the lights were out. She invited me in and we had a cup of tea.

She snuggled up to me on the couch as we drank. When I put down my cup, I pulled her to me and kissed her. She responded and our kisses deepened. I pushed my tongue into her mouth and she responded and our tongues were dancing. She broke the kiss and drew back looked at me and said,

"That was my first Ceilidh and I really enjoyed it. I have never danced so much in my life as I did tonight."

"I don't think you missed a dance for a Sassenach (a Gaelic word for the English, ) you were amazing" I said. "I am glad you are so beautiful that so many of the guys wanted to dance with you or I don't think I could have kept up."

"Do you really think I am beautiful?" She asked

"Carol Anne," I said. "In Glasgow we have an expression that sums you up. In the parlance a guy would say, 'You are absolutely drop down dead Gorgeous so you are.'"

She giggled, "That's bad grammar and real mixed metaphor if I ever heard one."

"Yes!" I said but it has a real ring to it and somehow I think it says it all, especially when it is applied to you."

She laughed and said "flatterer."

"Not true," I argued, "Flattery is when you exaggerate someone's qualities, and that is certainly not the case with you. You are truly beautiful and you are a very nice girl into the bargain."

She Giggled and said, "I think I will keep you around, you are good for a girl's ego."

"You will have no difficulty with that," I said, "I am more than willing to hang out with you for as long as you want. I would have thought with all the attention you get from the guys on the sales team you would be confident about your ability to attract men."

That's when it all came out. She was not worried about attracting men. It was what they would want from her when she had attracted them. Although in her early twenties she was still a virgin and was not ready to put out until she was married. She had strong Christian convictions about chastity until you entered the married state. She wasn't a prude she told me and she and her fiancé had done some caressing and fondling but only with all her clothes on. She did get worked up at times but she was determined to keep her feelings under control and would call a halt if she felt in any danger of losing it.

The engagement had lasted for two years, because her guy had been training to be an architect and there wasn't much money in it until he qualified. She earned a decent wage but he would not consider marriage unless he was the one who was able to pay the bills. I thought he was a bit of an idiot for thinking like that and even more so for leaving her for a girl who was prepared to put out.

She said to me, "There you have it, the sad tale of my romantic past. So now you have heard that, do you still want to hang around?"

"As I said," I told her "I have no difficulty hanging around with you. We have only had two dates and I have really enjoyed being with you on both occasions.

So I see no reason to change."

"I know we have only had two dates and I have enjoyed both of them, but I felt I had to be open with you about my principles, because I like you and I don't want to get involved to the point where I get hurt again because you want more than I can give."

"Well I'm not a Christian Carol Anne and I'm not a virgin either. You are a beautiful sexy looking woman and I can't promise not to make a pass at you, but I respect a woman's right to say no and when she says no, I take it that she means no. So let's just keep going and see what happens"

"I would like that" she said and so we did.

Over the following months we dated as regularly as my job permitted. I got on really well with her mum and dad and I enjoyed Carol Anne's company, even if I had to go home and whack myself off after a petting session with her. But despite what she had said, things did progress. Her father and mother went away to a friend's silver wedding one weekend and we had the house to ourselves. We had been out shopping and I had dutifully carried the parcels. When we got home she had started making the meal.

When she had finished her preparations and everything was cooking, she was tidying up at the sink I came up behind her and slid my arms round her front and pulled her back into me and nuzzled and kissed her neck. I felt her relax against me and without thinking I slid my hands up and cupped her breasts. I felt her tense up and started to move my hands away but her hands came up and covered mine and placed them back on her breasts. I continued to caress her through her clothes, and I felt myself hardening.

As I did I pressed myself up against her buttocks and I knew she could feel me, but she did not move away. I slid one hand down to her crotch and cupped it so that it was pressing into her pussy and still she did not do anything to stop me. Encouraged, I start to rub her crotch through the thin cotton skirt she was wearing and she gave a little moan. She did not say stop, but she turned round in my arms so that we were facing each other and it was impossible for me to keep my hands where they had been. She gave me a passionate kiss and rubbed herself into me. We continued like this for some time before she called a halt and said I was distracting her from her cooking.

She was not tea total and we had a glass of wine with the meal and another afterwards as we watched the television from the sofa. She sat close up to me and snuggled in and it wasn't long before we were kissing again. I found myself lying alongside her on the sofa and this time I slid my hands up inside the loose top she was wearing, and fondled her breast on the outside of her bra. Our kisses became more heated and my other hand slid up her thighs and caressed them.

After a few moments I moved my hand over her pussy and started to rub it and she was giving out little moans I rubbed my thumb over her clit and rubbed in circles and I felt her body jerk and stiffen and I knew she had a small orgasm so I took my hand away and kissed her passionately and drew back. I gently disentangled myself from her and said,

"If we go much further with this, I am not going to be able to control myself and you might do something you would regret."

Her face and neck were flushed, and she said, "Oh my, I have never felt anything like that before."

I looked at her in amazement and asked, "Have you never masturbated?"

"No" she said, "I don't feel it would be right to do that."

"But you do not what happened there?" I asked.

"I had an orgasm" she said.

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