Dirty Weekend With Cuckoldress

I had been with my beautiful girlfriend for about a year and we had a very interesting relationship. Of course I worshiped her as the gorgeous, dominant woman she was and we did lots of things together as a couple. But, I was her cuckold, giving her the freedom to have sex with other men. One night stands, regular lovers and sometimes, old flings.

This particular story starts on the run up to our one-year anniversary. I had arranged for us to go away for a nice weekend, booked a hotel with a spa and a gym, had nice dinner reservations for the Saturday night and was looking forward to spending some time with my wonderful girlfriend. She had been teasing me all week on the run up to the weekend, not letting me have an orgasm but playing with my excited cock each night for hours and edging me to the point of ultimate frustration but eventually denying me and telling me how waiting for the weekend would be worth it.

Of course this didn't mean that she was going without. I spent lots of time between her legs, pleasing her with my fingers, tongue and some of her many toys. She hadn't had a lover for a couple of weeks and was extra horny on the build up to the weekend too.

I had taken the Friday off work so we could have a relaxed drive to the secluded hotel and enjoy some of the countryside. However, the drive wasn't quite as relaxing as it could have been for me. She had insisted on me putting on my chastity cage Friday morning before we left, something we often did to raise the teasing level. She then spent the entire journey trying her best to tease me and make sure that I was uncomfortably shifting in my seat the whole way. She whispered in my ear about how horny she was, told me that her pussy was already wet with anticipation of the steamy weekend (a fact she proved by slipping a finger inside and rubbing her juices across my lips) and naturally knowing my weakness for her sexy feet, she had them up on the dash, in my lap or occasionally up to my face for me to kiss. In any event, my idea of a relaxing weekend wasn't quite going to plan so far.

When we arrived I took the bags up to the room while she had a look around the facilities, particularly the gym and spa. She was in terrific shape herself from years of good diet & exercise and had helped me get back into reasonable shape since getting together. Naturally she drew lots of male attention when working out in her tight lycra outfit and she was never short of an offer to help her with weights or anything else. Although we often worked out together, she was always partial to flirting with some guys in the gym.

We met back in the reception area where she told me she was very pleased with the facilities and wanted to see the room. I led her upstairs with a bit of fear, hoping she would really like the room I had booked. I needn't have worried, she loved the room, especially with the view and the balcony and she attacked me, saying thanks and showering me with kisses. Soon the kisses became more passionate and she began rubbing her lithe body against mine, causing plenty of discomfort to my caged cock.

She made me lick her to three orgasms right there as she lay back on the bed before we headed out to explore the local area a little on Friday afternoon. Needless to say, my cock remained untouched, unlocked but sore and swollen for the entire time.

The local area was really nice and we enjoyed seeing some sights and found a nice cozy little put for dinner before heading back to the room fairly late. In a move that was slightly out of character, my girlfriend suggested that we head to bed early and rest up for the Saturday. I was a little shocked when she said that as I expected her to take another opportunity to tease my caged cock and enjoy my oral skills. I ready for bed first and busied myself on my phone while she finished up in the bathroom. When she came out my jaw dropped, she was wearing a silky nightie with lacy sections that clung to her beautiful curves and made her look amazing.

As she slipped into bed I lent in to kiss her, placing a hand on her hip thinking she had changed her mind about the early night, but she said.

"Slow down there cowboy, no naughty stuff tonight, I'm tired and need my beauty sleep". She then patted my caged cock.

"You'll just have to wait for tomorrow for some fun."

She then rolled onto her side, flicked the light off and snuggled back against me to spoon. I lay down in a state of surprise, she normally took every opportunity to tease me and pretty much never went to sleep without a little 'good-night' orgasm.

After a few seconds in the dark I tried to forget about it all and take my mind off the fact that I was still wearing the chastity belt. We played around with the belt quite a lot but I didn't often wear it for long periods of time and rarely overnight as it led to very uncomfortable sleep. Just as I was starting to think about this I felt her hips shift a little as she rubbed her sexy ass directly against my caged cock. It was only for a second and I assumed it was just instinct, but then it happened again, and again.

Thinking this was more like it I moved my hand from her stomach up to her breast, squeezing and feeling her nipple harden. She grabbed my hand and replaced it on her stomach, firmly telling me she had said no. This happened again twice and I heard the giggle in her voice the second time. She was always messing with my mind and tonight was no different. After about 15 minutes of this uncomfortable teasing I heard her breathing unmistakably quicken and realized that she now had her hand between her legs. She gave herself a quick orgasm while constantly grinding back against my poor imprisoned cock and then drifted off to sleep.

My night was very restless, trying to keep my mind of the beautiful Goddess sleeping beside me was tricky enough but all of the teasing that week had done the trick, I was going out of my mind with excitement and was eager for the treats that Saturday would bring. But the constant ache in my balls from the unyielding plastic cage was close to unbearable.

I finally managed to drift into a fitful sleep a couple of hours before dawn but it seemed like second later that I was woken up by a sharp pain in my privates. It took me a few seconds to focus and see what was going on. My beautiful girlfriend was between my legs and was giving my caged cock a blowjob. I couldn't feel anything except a bit of warmth from her mouth but the pain was intense as my desperate cock tried to escape.

She giggled at my discomfort and said "morning sleepy head, don't you just love a good play in the morning?" in a breathless voice and then I heard the sound of her vibrator which she was clearly enjoying. She shuffled up my body and told me to make myself useful and please her with my mouth, which of course I happily did.

We had a leisurely breakfast and went for a gentle walk in the surrounding countryside before heading back to the room and getting ready for the gym. Of course all eyes were on her in her sexy little workout clothes as she stretched and sweated her way through her session plan. I did notice one particular guy that seemed to catch her eye, although it was a bit more discreet than usual I definitely saw the signs that she was keen and every time I looked over, his eyes were on her.

We finished our workout and were upstairs in the little café having a drink and some light lunch when I spotted him come in and grab a seat not too far away from us by the window. My heart sank a little when I saw my girlfriend bite her lip and stare at him. She was clearly keen and judging by the flirty glances he was too. After a brief discussion where I moaned that this was supposed to be our weekend, she put her foot down and gave me my orders.

I slowly walked over to the gentleman and hovered by his table, he looked up at me with a confused expression on his face. I turned a deep shade of red and stared intently at a napkin on the table as I said to him

"My girlfriend would like to know if you're free for dinner tonight." He stared at me speechless and clearly not sure whether I was being serious.

"If you are, this is where we have booked for dinner, she hopes to see you later" I dropped a napkin on his table with a time and the name of the restaurant we would be eating at, sealed with a kiss from her cherry red lips. I hurried back to our table embarrassed and a little excited about what I'd just done. I sat down to a "good boy" from my girlfriend and we then moved on to discuss other things.

We went out again to see a little bit of the town before heading back to the room to get ready for a special anniversary dinner I had booked. I had brought a nice blue suite and I knew that my girlfriend had bought some new, very sexy lingerie for the weekend and I was looking forward to seeing her in it and hopefully having some fun too.

We have a tradition wherever possible that I help my girlfriend get dressed before she goes out on her dates with other men. It adds to the teasing element and she always gets me so worked up by thinking out loud about what her date is going to be like and what they would be doing.

This time was no different and I saw the beautiful seamed stockings she laid out on the bed, the matching satin bra, panties & garter belt set, accompanied by a deep red figure hugging dress which was conservative enough to not draw open criticism but did nothing to hide her fantastic figure.

I was shaking as I helped her into her underwear, then carefully rolled the stockings up her long sexy legs. Helping her slip into that beautiful dress before finishing off the outfit with a pair a gorgeous classic black Louboutin stilettos. She made me place a kiss on the tip of each shoe when she was ready and added a little anklet with a chain on, an advertisement to those in the know that she was available.

All the time she was dressing she wondered out loud about whether the guy from the gym earlier would actually turn up or not. She had purposefully put the time on the napkin 30 minutes later than our booking.

"Wouldn't it just be so deliciously humiliating for you if he turned up part way through our starters and made you leave so he could take over?" she mused. "What do you think people would say when a tall handsome man comes in and takes your place?" I couldn't manage a response and was desperate for him not to turn up. I really wanted to enjoy our anniversary.

I quickly got dressed and we headed out to the restaurant, of course she turned heads everywhere she went and lapped up the attention with a big smile on her gorgeous face. We settled in, having a pre-dinner drink and I had forgotten all about the other guy as we enjoyed our starters. She toyed with me in a low voice, telling me how naught she was feeling and couldn't wait to get back to the room. She ran her sexy high-heeled foot up my leg and tapped my caged cock with the tip of her heel, causing me to moan.

I saw her shifting around a little in her seat and thought she was uncomfortable for a moment but she just smiled and I thought nothing of it. She reached across the table and placed something next to my wine glass and said "I don't think I'll be needing these tonight anyway" with a huge grin on her face.

I looked down and saw her panties in a ball, quickly grabbing them and shoving them into my pocket I was not surprised to feel her wetness on them. And I brought my fingers up to my nose to smell her scent as I grinned wildly back. It really was going to happen, I was so excited... and then I felt a big hand on my shoulder...

To be continued.