Caroline and I had been together, on-and-off, for a little over 2 years. She was lovely. Warm, funny, loving and hot as hell. At 5’4″, she was not tall, but had a nice figure–sweet ass and shapely legs–coupled with a pretty face, long auburn hair, and a knockout smile. She was the woman I wanted to spend the rest of my life with; I just hadn’t got round to asking her that question yet.
The reason for this was not my (pathological) fear of commitment; rather, it was because over the last 2 years we had split on several occasions. Truth be told, it was these splits that made me realize how deeply I felt for her. It physically hurt when we were apart.
We stayed ‘friends’ during each split. One evening (during one such ‘split’), we were alone in Caroline’s flat, (that’s apartment for US readers). After a little too much wine she told me she had been seeing an old boyfriend. I was shocked and devastated.
“It’s Ok,” she told me having obviously seen the expression on my face, “it’s just sex.”
“What!” I screamed internally, who did she think she was — a man?
We talked for a long time that night. He was an ex who she had dumped, as he was also a bit of an ass. He was now married with one child and a second on the way. She had been horny as hell, and he was a good lover. Slowly, it emerged that we had serious problems in the bedroom. I (actually, Caroline), suffered from my premature ejaculation– it was a rare event for me to last more than 2 minutes inside her.
When we were together she would tell me things like, “It’s OK”, and I enjoy the intimacy”, but it wasn’t true. When it comes down to it every woman needs a good fucking– at least occasionally.
We talked long and it became clear that the underlying cause of our regular breaks was simple, sexual frustration. She loved me, but this was a serious problem that meant we could have no future. She wanted to get back together but had concluded it was over; the on-off-on-off nature of our relationship was too painful, for both of us. She was right.
The prospect of us being seriously ‘finished’ hit me hard. A thought passed my through my head, it was over my lips, before I had a chance to think.
“If it is just sex with this guy, ” I started, refusing to acknowledge his name. “What if you could keep seeing him? Do you think we could have a chance?”
I hadn’t considered the full implications of what I had just said. I gathered from the deafening silence, clearly Caroline was doing that now. It wasn’t as ridiculous as it may have sounded; We were finished and therefore had nothing to lose. Worst-case scenario, we were both pretty drunk and when the cold light of day led to a reassessment of the proposal, we could write it off to that.
Finally she spoke.
“No.” It was a socially correct answer, and the correct reply from what was basically a ‘good’ girl.
“No; we couldn’t… It’s wrong,” She queried.
“What’s so wrong?” I inquired.
“I love you. I need to be with you, and will do anything to make you happy. Ok, this isn’t exactly what I had in mind but if that’s what it takes then so be it.”
“We can’t.” She protested.
“Do you love him?” I asked.
“No. I’ve told you already, its just sex.” She replied.
“Then I can live with it, it’s like..” I was struggling for a suitable metaphor.
“It’s like going to the hair dresser, something you need that I cannot do for you.” I let the thought sink in.
“What do we have to lose? Think about it; I will. It’ll probably just sound crazy in the morning.” I ended with a chuckle, kissed her on the forehead and left.
* * *
3 days later text message arrived. “U serious?”
A simple reply was all that was required, “Yes.”
The next one arrived. “Can I come over tonight?”
“‘Course you can. 8pm curry?”
* * *
8pm–Caroline is always punctual–the doorbell rang out. She was standing there looking as hot as ever, clutching a bottle of wine. I enjoyed the view just a little too long.
“Aren’t you going to invite me in then?” she asked with a giggle in her voice.
It was uncomfortable at first, like a first date. Neither of us would raise the subject, although we both wanted to talk about it. We ordered the food (if you’d ever tasted my cooking you’d know why we ordered food!). It wasn’t until after the meal, and a few glasses of vino, that we finally got onto the subject.
Once we started talking, it was impossible to stop. We had both given it a lot of thought and once again we talked for hours. By 2 am, we had agreed the following guidelines:
1. Total honesty. Neither of us were in any doubt how difficult this would be, nor that deception/concealment would make matters much worse.
2. Caroline would answer any questions I had, which included what had/had not happened; she would tell me only what I asked nothing more, nothing less.
3. We would do this once, and then decide if we could carry on.
4. Anywhere but here. This was our home. Caroline had kept on her flat due to the fact we broke-up so often and for extra storage space.
5. Safe sex.
* * *
2:05: We were in bed making passionate love.
2:07: We, meaning I, had finished.
She moved back in the following day.
* * *
We were good for about a month. The conversation and agreement had been pushed to the back of my mind. It was not to stay that way.
One night after dinner Caroline asked me, “Can I go out next Friday?”
At first I did not realize what she was really asking, “Of course you can. Why are you asking?” It was only after the final syllable left my lips that I understood.
She blushed and stammered, “That’s not what I meant. I…” her words trailed away.
Relieving by her clear embarrassment, I interrupted. “Ah, think I know what you’re asking, and yes you can.”
It was a long week until Friday.
* * *
Friday I was at the office, in body if not in mind. When I went home, Caroline was cooking dinner. It was a vision of domestic normality. We both picked at the meal before she went to get ready.
I was padding around behind her like a lost puppy my stomach was churning. It was only now that the full implications of our arrangement were sinking in, and it wasn’t nice.
She showered, shaved and plucked. Hair was done, then make-up. Lingerie, skirt, blouse and shoes. She looked stunning. She also looked nervous.
“Are you sure about this?” She asked.
“No” I replied honestly.
“I’m not sure; I know I love you,” I could see her emotion but I continued, “I love you but I need you to be happy, I want you to be happy, and I know this is one area which I cannot do that for you. I also know that this is our last chance to be together, or we’re finished. Go, do this, I’ll be here when you get back. You look fantastic by the way.”
With that final comment the tears finally came. This was not something she was prone to; I hugged her. After a minute or so, she turned to the mirror.
“I look like shit!” She said reaching for a face wipe and scrapping the mascara off.
She re-did her make-up and left.
The next 4 hours were the longest of my life. I tried to watch TV. I surfed the Internet. I even drove to his house and sat outside for a while. Nothing could take my mind off what was happening. Nothing could remove the nausea in the pit of my stomach. I drove home, showered and went to bed.
It was a little after midnight when I heard the car pull up to the house. Engine died, key in the door, Caroline’s footsteps entered the hall, and headed for the living room. It was a good 15 minutes later that I heard her come up the stairs. Instead of coming into our bedroom, she turned and went in to the spare room; it doubled as a dressing room. I waited. I could hear her moving around, then silence. I waited another 5 minutes and realized she wasn’t coming through.
As I opened the door I could see Caroline was in bed. I got in behind her. She did not stir. Moving across the bed to her I put my arm around her, our bodies spooning together, gave a little squeeze, and kissed her shoulder.
“I love you” I said quietly.
At that moment, I just wanted to protect her. She did not reply, but I know she was crying very gently– trying not to be noticed. We remained in that position for the rest of the night.
* * *
The following evening, as agreed, we had the talk. She had gotten as far as the front door and after ringing the bell she stood there thinking, arguing with herself. She had just decided to leave when the door opened. She went in. The sex had been good but, on this rare occasion, she had not cum because she couldn’t completely let go. My instinct told me this was a lie, a lie to make it easier on me, a lie I could live with. I also modified the truth just a little; telling her it was tough but playing down just what a torrid time I had had.
* * *
It was a good 2 months later before her next ‘date’. Life had been good during that time.
Again I watched her get ready. Her routine was very much as before until, once again, she was looking fabulous. My stomach was doing somersaults again, not as bad as before, and for the first time, tinged with arousal.
She returned home earlier that night than she had from her first outing. I was waiting for her. When she came in, I literally pounced on her. I kissed her. It was not in a loving way but in a forceful, I’m going to have you–right now–manner. We had rough, almost violent, sex right there in the hallway. It was passionate, but very aggressive. Panties were pulled off – she was violated. It was animalistic, Neanderthal behavior, so out-of character but I had reclaimed what was ‘mine.’
“Where did that come from?” She asked once we were done.
“I don’t know,” I replied with an embarrassed laugh. “It’s Ok now, that madman’s gone.”
“That’s a pity!” She said in a humorous, slightly mocking tone, “I kind of liked him.”
We laughed, and got up. As I fixed us a drink, Caroline cleaned herself up.
“Tell me all about it.” I requested and she did.
The reason for the earlier start/finish was his wife. Tonight she (the wife) had been visiting her sister; the first time she was on a girl’s night out.
Caroline and her lover had sex twice. The first time had been a quickie. What’s known in the UK as a knee trembler– up against a wall. Skirt pulled high, panties had already been removed before she arrived. (When she was sitting in the car outside she had slid them off in anticipation of an early fuck.) She had cum with her legs around his waist, supported by the wall.
“It felt so good feeling him pulse inside me, and yet so strange not to be followed by cum filling my cunt.” She explained.
They had then gone upstairs; he slowly undressed her, laid her on the bed, and begun kissing and caressing her naked body. This progressed to a slow, sensual massage from her feet to her shoulders, carefully avoiding her pussy to build her anticipation. By the time his fingers had worked their way back down, over her breasts and down her sides, she was wet and aching for him.
They were kissing passionately as his fingers moved, with expertise around her nub, teasing it, gently encouraging it out from beneath its protective sheath. When the time was right, he slid a finger deep inside her. His thumb was working the external nub, while his finger circled her spot. She was cumming again. It was good but what she ached for was cock.
After She had cum and regained her composure, she had pleaded with him to fuck her. She pushed him over and moved onto her front, raising her ass into the air. He had not needed to be asked twice and entered her from behind. Although he had a good-sized cock, it entered easily. He pinned her head down onto the pillow and had her cumming another twice before his own orgasm. He unloaded in her. They collapsed in a sweaty heap. Satisfied, still tingling a little, she dressed and left.
Listening to her describe her evening, 2 things hit me. The first was her language. She was normally so prim; to hear her “getting fucked” and “aching for cock “was so unusual. The second thing was how hot it had made me. We headed to the bedroom and fucked twice. Her recollection of the evening had obviously got her hot as well, which explained the language, as she was soaking when we arrived in the bedroom.
* * *
It wasn’t until her next date that I considered myself to be in a cuckold relationship. Until now, in my mind anyway, this was more a one-sided swinging/loving wife type scenario. That was about to change!
It was to be another late night. Caroline had told me not to wait up; in fact she insisted I be in bed when she returned.
It was nearly 1am when she returned. This time she came directly to bed.
She entered the darkened room. Although I had tried, I had not slept; a raging cock had seen to that. The light flooded in as she stood in the doorway. Stilettos, stockings, no skirt or panties, her blouse open, breasts encapsulated by her lacy bra. Wow!
She moved slowly now, encouraging me to enjoy the view.
She came and stood beside me, then pushed my head back onto the pillow.
“Now,” she said assertively, “I have been fucked senseless tonight, my little cunt has taken a pounding and now you..” she paused for effect “You are going to soothe it.”
With that she got onto the bed, pinned my head between her legs, and lowered her pussy to my mouth.
Already hard in anticipation, and then from the “floor show” this new turn was almost too much. My cock was aching as her cunt approached.
The first thing that struck me was the smell. She stank of sex. The musky scent, mixed with her own arousal, added to the latex from the condom(s) was a heady mix, and my tongue was eager to explore.
Her clit was protruding as I cupped my tongue around it. Gentle and moist, I parted her lips and caressed the clit. She relaxed into it and began to tell me all about her evening. She told me about his cock, it wasn’t especially long about the same as mine, which was about 6.5 inches. It was thick though and would force its way in; pound her tight cunt expertly, in a controlled rhythmic manner, before accelerating and violently crashing into her before exploding.
As she was telling the details, she was obviously recalling the night’s events. Her pussy was grinding into my face, keeping pace with the memories. She had shifted position, taking my tongue from her clit into her slit. The taste was strong but good. I was licking and dipping trying to keep the pace she was setting. She was–in her story–just about to cum.
“Next time,” she stated, “I’m fucking him without a condom. He’s going to fill my cunt, dump his huge load deep inside me.” As she made the announcement, I felt her tense and cum on my face. A fresh gush of moisture came, and was eagerly devoured as she slowed.
When she was finished, instead of climbing off, She stayed there, a mischievous grin breaking out across her face. She brought her pussy back to my lips.
“It’s not clean yet!” She announced.
I went back to sucking, and licking her pussy and clit. She was maneuvering above me, and then it came. Just a tiny dribble at first, my tongue was right there and quickly licked away the bitter fluid. Then more, an acrid shot hit the back of my throat, and started to fill my mouth. Swallowing as fast as I could, it was still difficult to keep up. She was pissing directly in my mouth! It was something I had fantasized about, had read about, and once (long ago) mentioned, but nothing had ever come of it.
“You like that?” She asked. It was as much as a statement as a question. From my frantic lapping and the ache in my sack, it was impossible to answer her.
She supplied the reply herself, “Yes, of course you do. Get used to it, you’ll be cleaning my filthy cunt much more in future.”
With that She reached behind, and started tugging my aching cock. It exploded almost immediately, and was awesome.
She stopped peeing. Then she gave me a big kiss on the lips and climbed off.
That was the night I first considered myself a cuckold. Things were going to go further in future, but the groundwork was now set.