It was clear after our first two months that we needed to plan our sex challenge much better. We already had a heavy bias for vaginal sex at home, so we needed to balance things up to complete the challenge. So, before the March challenge, we planned all the remaining anniversaries (in outline form) to ensure we got the balance right.
There was only one anniversary in March, and that was our first anal sex. I had offered him my ass to fuck a little over six weeks after we got together, and that first time was tentative and gentle. The anniversary anal was far from that. He was huge and confident, so he could vigorously drive into my asshole with his long hard cock. We were staying with a friend, so we had to excuse ourselves for a while so that he could give my asshole a thorough workout in her guest bedroom.
There was also only one anniversary in April, and that was our first outside fuck (which was vaginal and was originally in a field by the layby we were parked in). That layby isn’t there anymore, so we decided on another layby close by. In a mirror of the original event, we laid out a blanket in the field behind a hedge, he lay me down on it, lifted up my skirt to above my waist and fucked me right there. I was already sopping wet at the thought (and he was already hard), so his entry was fairly easy. He managed to make me cum before he exploded, and we got back to the car fairly quickly afterwards. I spent the rest of the car journey oozing (as he likes me to be) and he only cleaned me up when we got home.
There were four anniversaries in May, first was the anniversary of the first time we fucked in a car. It was the early hours of the morning and we were parked in a car park high on a ridge overlooking a city. This was a popular spot with locals during the day but was deserted in the middle of the night. So, in the case of the original act and the anniversary celebration, we flattened the back seat and fucked in the boot, my cunt getting a good pounding from a very excited (and therefore rock hard) husband.
Later that same week, we celebrated the anniversary of our first fuck at his parents’ house (which was anal) by again having anal at his parents’ house. They are used to us fucking now, so it came as no surprise when we slipped off for a bit of us time. This time though, I was feeling able to stand for anal, so he pinned me to the wall and drove his cock into my ass, the unyielding wall meaning my asshole was the recipient of every millimetre of his drive. I’m not often up to this our most invasive anal fuck, but today I was and the fact it was at his parents’ house made it even more naughty.
A couple of weeks later, we celebrated the first time we had anal somewhere other than our house by having anal on a friend’s sofa. She had to pop out for an hour, so we convinced her to be out at the time we needed so we could have anal at the right time. I spent the rest of the evening with a slightly lubey ass crack as a reminder of my ass fuck, and I didn’t wash until I got home.
Finally in May, we celebrated the first time I pegged him with an audience by pegging him in front of our friends Laura, Nikki, and their husbands.
In June, there was my birthday, so we again did anal in a friend’s house. She knew of the challenge, so was happy to oblige. As she lives in a one bedroom flat, we had to use her bed, and we’re fairly certain she sneaked a look while he was impaling my ass.
In July, we celebrated our first fuck in someone else’s home by having anal in that same friend’s flat. This time, she just asked if we minded her watching and masturbating whilst we did. Of course, we didn’t mind, and this time, we put a cushion under my belly to raise myself up and to give her a good view of my cunt and asshole, as it was being impaled. We all seemed to enjoy ourselves.
In August, we had the anniversary of our first outside pegging. We originally did this in our garden, but we’ve since moved and no longer have a garden, so we had to borrow Laura’s garden to achieve this.
In September, we celebrated the anniversary of having sex in my graduation robes (I was a mature student, so this was only three years ago). I originally settled on anal, as I thought my outfit might have been compromised by having vaginal sex at the time. So, the anniversary was again anal in my robes. We originally fucked in a quiet place on campus, so we went back, loaded me into my robes (and only my robes this time, and he anally fucked me in a similar place). I love the juxtaposition between my robes for my first class degree and anal penetration in a very practiced manner.
October was the anniversary of our first watersports. This was our first anniversary at home for some time, and indeed all the remaining challenges were at home (a combination of it being colder outside and people being busy in the run up to Christmas). So, we had an evening of watersports, and he fucked my cunt in the wet room at the appropriate time whilst my ass was in a puddle of my piss.
We concluded October by us again having vaginal sex in front of other friends to celebrate the anniversary of having vaginal sex in front of those same friends (and others).
November was the anniversary of our first pegging, so Victoria and I spent the whole evening pegging his poor ass (at home) and spanking him a bit in between. At the right time, I was pegging him, but Victoria did most of the hard work, as I wasn’t up to pegging him for as long as I wanted to.
In December, the first anniversary to celebrate was the first time he drank my piss, so as well as drinking my piss regularly throughout the day, he fucked my ass at the appropriate time.
The final anniversary was his birthday, so he had the now traditional birthday pegging, only this time because I was feeling quite good, I pegged him a number of times over the course of the day.
We ended the year with a vaginal fuck over Big Ben’s bongs as we always do (although we haven’t counted that, as we counted the one at the start of the year).
So, we successfully completed the challenge. We had sex in our home 8 times, inside but not in our home 8 times and outside 4 times. We also had vaginal sex 8 times, anal sex 8 times and pegged him 4 times. The challenge took quite a bit of organisation, but it was great fun.
2019’s challenges are not so prescriptive. They are to increase the amount of anal and pegging that we do. I want to get to 50% anal 50% vaginal (ideally without reducing the amount of vaginal I have), and I’ve been wanting to train his asshole to take larger toys, and you can only do that by regular and thorough pegging. Yes 2019 is the year of the penetrated asshole, and I’m looking forward to it!