Saturday Night Sissy
- 2 years ago
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Saturday With Al free porn video
After a great night of sleep, I awoke Saturday morning thinking of spending the day making love to Al.
After coffee, I drew a nice hot bath and proceeded to spend the next thirty minutes getting clean and smooth. After drying off I applied liberal amounts of a lavender-scented lotion to keep me soft and smelling nice. I also made sure that my feet were quite soft as well, since that seemed to be his favorite place to start.
While I was deciding what to wear, I called Al to see if he had any plans in mind so I knew what to bring along. He hoped we could spend some time in bed but he also had a pool if we felt like swimming. He also said that since his house was on ten acres and surrounded by trees, clothes would be completely unnecessary. That last statement really got me going since I was hoping to wear some of my girly things to his place.
I told him that I had a few more things to do but that I should be to his house around noontime. Al replied that he couldn’t wait and even said that he hoped I would consider spending the night. I told him that I would think about it, but that we could decide that later. After hanging up I knew that I would definitely be spending the night!
The extra night changed some things so I went about planning how much to bring and how often I would want to change. I really wanted to make it an unforgettable weekend for both of us since we seemed to get along so well. Knowing that he was hot-to-trot for sex as soon as I got there made me want to look as sexy as possible right off.
I decided on getting quite girly, painting my toenails pink to match my press-on fingernails. I did consider a wig but decided against it since he had already accepted me as a guy. I just felt it wasn’t necessary and styled my hair more like a girl. Putting on some light makeup to soften my look, I also added some pink lip gloss.
As far as clothes were concerned, I chose to wear my purple and black lace corset with matching panties. The black thigh-highs and my five-inch heels were also added to complete the ‘ready for business’ look. Of course. I brought along several other items including my black see-though romper. Once I was all put together I pulled on a t-shirt and a pair of sweat pants for the ride.
Al’s house was out on a country road and his closest neighbor was about half a mile away. Pulling into the driveway, I realized that he wasn’t kidding about the house being surrounded. Other than an opening for the driveway, there was no way you could see the house from the street. With the house set back a few hundred yards you only got a fleeting glimpse as you came upon it.
Coming to a stop in front of Al’s garage I quickly removed my t-shirt and sweat pants. As he opened the front door and started heading my way I slipped on my heels and stepped out of the car. The outfit seemed to have the desired effect. His eyes got wide and he practically ran over to me. Wrapping his arms around me he leaned in for a very aggressive kiss and quickly began squeezing my ass with both hands.
A couple of minutes later we finally slowed down enough to talk and the first thing he said was, "Can we go to the bedroom now?" I pulled away from him long enough to grab my bag as we headed for the door. While we were walking he couldn’t keep his hand off of my ass. Entering his home, we never stopped moving until we walked into his bedroom, which had a king-sized bed. As we entered the bedroom I dropped my bag next to the bed and turned to kiss Al again. As his hands focused on my ass I had my right hand on the back of his head and my left between us to see if he was ‘ready’. I had actually hoped that he would still be soft so that I could perform some oral service before we got down to the deed.
Al was already quite hard so as our lips parted I removed my panties and lay back on the bed. He quickly removed his pants and stepped up to my ass while pushing my legs back to my chest. He started rubbing his pre-cum covered cock against my ass and slowly began to enter me. He took his time sliding in and out while standing. Soon he asked me to slide back further on the bed so he could lie on top of me.
Knowing that he enjoyed playing with my nipples, I pulled the corset down enough to expose them as I slid back on the bed. Al took the hint and began sucking and pinching them to my delight. He must have been really worked up because it wasn’t more than a few minutes in before he was grunting and cumming.
Al noticed that I hadn’t cum yet and gently squeezed my cock. He started pumping it while still moving slowly in and out of me. I just laid back and enjoyed the feeling and when I was really close I pulled his face to mine for a sexy sloppy kiss as I came between our bellies. We just laid there for a while kissing and talking as his softening cock slowly left me.
When we finally came up for air Al asked if I was hungry. I told him that I was quite hungry and needed to clean up a little. He got up and helped me up like the gentleman that he is. He showed me to the bathroom and after cleaning himself he headed to the kitchen saying he would get lunch started. I decided to remove the corset, as they can be uncomfortable over long periods, and got cleaned up too.
Since Al had said that nudity wasn’t a problem I removed everything else and just went with the black see-through romper, which left nothing to the imagination. Walking barefoot through the house, I took my time and looked around to try to get a feel for who Al really was. I got the impression from the extensive collection of photographs that he was well liked by friends and family.
When I entered the kitchen he nearly dropped the salad bowl that he was carrying to the table. He then blurted out how sexy I looked and that it was going to be a fun weekend.
While we were eating we had our first real conversation about sex and our preferences. We both admitted that as we have aged we have become much more open to things that we would never have done in our younger days. I told him that I had always enjoyed anal stimulation and penetration even when I was strictly heterosexual.
Continuing on, I also admitted that for most of my life I’ve felt more feminine than masculine. That femininity is definitely what led me to be open to homosexual encounters. I also told Al that I never aggressively sought sex with other men but that it just seemed to happen, like it did with us. Up until now it just seemed to be something that the other person needed at the time and it never went beyond a few dates.
Al admitted that since his wife had passed he started finding other women and men sexually attractive. He said that he just never really looked at other people sexually while his wife was alive. Although it hadn’t been very long since we first had sex, he didn’t really think of himself as gay just because we had sex. Since I presented myself as a female sexually, my masculine attributes didn’t seem to matter to him.
After we finished lunch Al led me to a couple of lounge chairs next to the pool. As I began to sit down he squeezed my ass and asked if I wanted a drink. Smiling, I asked him what he had. He said he had some beer, some wine or he could make me a mixed drink. I asked him if he was trying to get me drunk and take advantage of me, as I squeezed his cock through his pants. When he blushed I told him that I’d have a vodka tonic with a slice of orange, if he had it.
When Al returned with my drink he asked if I was interested in going for a swim. I told him that if he was going to skinny-dip I would be happy to join him. He said he needed to grab some towels and would be right back. When Al returned he dropped the towels on his lounge chair and kicked off his sandals leaving him completely naked. As he stepped into the pool I stood up and finished my drink in one shot. After removing my romper I followed him into the water.
Diving under the water, I swam about ten feet past him and came up to float on my back. Floating along with my eyes closed, I could hear Al getting closer and knew that he was up to something. I considered peeking just long enough to see where he was, but I really wanted him to surprise me with his first touch. He seemed to be circling me to get me worked up and I’m sure he could tell it was working.
The anticipation of his first touch had me so excited that both my cock and nipples were quite hard. I had a feeling that he would start at my feet and I wasn’t disappointed. But what I hadn’t thought of was that he would use his tongue and lips first. Al started on my left foot licking and sucking on my big toe. He took his time working on each toe in succession, sliding his tongue in between them and sucking each. His patience and thoroughness led me to believe that he thought he could make each one of them cum.
I can’t remember ever being that close to cumming without being touched in my genital region. As he was finishing up with my left foot he started gently pulling my right foot closer so he could move easily to that one. In that excruciating five seconds that it took Al to remove his lips from my left foot to my right, I realized that I had been moaning quite loudly. As he started on my right foot I opened my eyes and noticed that the pre-cum was flowing from my pulsing cock.
I’m sure Al saw it too, because when he noticed that my eyes were open and what I was looking at he really started working. Closing my eyes again, I focused on the exquisite sensations that he was producing on my toes. When Al started to lightly scrape the bottom of my big toe it sent me over the edge. As I started to cum I could feel it hit my belly and hear it hit the water.
As my orgasm subsided I could feel Al parting my legs and moving towards my crotch. I opened my eyes just before he started to lick my shrinking cock clean. I let him go for a minute or two and then told him that it was my turn to take care of him. While I was dropping my feet to the pool bottom, I asked him if he ever had an underwater blowjob and he said that he hadn’t.
Taking a deep breath, I dove under the water to find a very hard cock in need of sucking. Initially, I tried licking him and found that it was difficult to keep the water off my mouth. Taking him into my mouth made it easier to maintain a good seal and keep from drowning. I began sucking and pumping up and down but found that it was slow going under water. So I wrapped my hands around him and grabbed his ass for leverage which improved things tremendously. I still had to come up for air every minute or two which seemed to break the momentum each time.
Deciding that the underwater thing just wasn’t working for me, I slowly pushed Al towards the steps as I went under one last time. By the time we got to the steps I needed to come up for air anyway and I told Al that we needed to dry dock this blowjob. I lead him to the lounge chair and as he lay back I began again. This time I was able to lick him all over his cock and balls without drowning.
I could tell that I had him going now and as I started sucking him in earnest I also spread his legs. With his legs spread I was able to lightly run my finger across his asshole. Every time I did he jumped just a little and pushed his cock harder into my mouth. I took some of the spit that was running down his cock and balls to use as a lubricant to slowly enter his ass with my finger. Before I got it half way in he started filling my mouth with his cum.
When he was finished he pulled me up to his face and started kissing me again. As we were winding down Al suggested that we head to the bedroom for a little nap. Slipping under the covers, I backed up to Al, so that we could spoon while we slept and sleep we did. I woke to Al’s semi-hard cock pushing between my ass cheeks and his hands squeezing my chest and nipples.
Waking to the attentions of a very appreciative lover is always a plus and I never wanted it to end. As I could feel that his cock was getting harder I grabbed the bottle of lube that I left on the nightstand. Raising my free leg I squirted a little on my hole and his cock which made things much more fun. Suddenly he was balls deep and we were both moaning. Knowing that it would be difficult for him to go much longer in that position, I rolled on top in a reverse cowgirl and went crazy.
Alternating between crazy fast for a few seconds and slow and deep for a little longer had us both on the edge. Al didn’t seem to care for me facing away from him and asked me to please turn around. After turning I still kept alternating between the fast and slow fucking until I knew he was very close. Then I leaned down and started kissing him as he started cumming inside of me. As he came he thrust hard up into me which caused me to cum as well.
Al always enjoyed the aftermath even more that the actual orgasm which was fine with me. There isn’t quite anything as nice as cuddling with a lover with or without the orgasm. We lay in bed for the better part of the evening and finally got up only when our growling stomachs demanded it. We settled on some cheese and pretzels for a snack as we cuddled up on the couch like an old married couple.
Haven
- 01.10.2021
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- Category:
- Crossdressing
