Sierra is this amazing trans woman that I met in the mid 90's and had a wild relationship with. At first it was just lust and it turned out to be an incredible love in my life.
A few hours later, while I was at work, Sierra comes in and is dressed in one of her spring dresses that drive me crazy. Her ebony skin was radiant today and it had everyone in my office paying attention to her. My two buddies still whispered “fuck you” as I walked by them; I just laughed under my breath.
I asked her what she was doing here and she said she brought me lunch and she was going to the salon, she needed to relax, and then maybe some shopping. I laughed with her and she handed me my lunch and I tried to kiss her but she turned her head away saying “lipstick baby.” I heard my two coworkers laughing at me and she joined in with them.
When I got home from the gym, Sierra was there making dinner and looking amazing in her new hair, make up and nails. I loved her look when she went natural but the new make-over is what she needed today to help take her mind off of her ex in Orlando. She greeted me at the door still in her dress from earlier, but barefoot. I already knew the deal, I got a kiss but that was it until I had a shower. After my shower I walked back out to the kitchen in just the powder blue thong she bought me and she had that devilish grin on her face again. She told me to put some clothes on for dinner, which I did and then we ate dinner and had a drink. After dinner she told me to take my clothes off and wait for her to shower. I got undressed minus my thong and picked all the dishes up. About 20 minutes later, Sierra came out of the bedroom in new lingerie that matched the color of my thong, powder blue. Her ebony skin tone against the powder blue cloth was absolutely exquisite. She had bra, thong and thigh high stockings that matched, my jaw hit the ground and my cock stiffened immediately. I followed her to the bedroom where she had already lit some candles and turned some music on. She crawled up onto the bed on her hands and knees and seductively looked back at me. I smacked her on the ass like she had done me over the weekend and she let out a little whelp and a huge smile. Then I playfully bit the same ass cheek and she jumped forward giggling. I climbed up on the bed over her legs as she laid on her stomach. I took both my hands and ran them up her legs from her ankles to her ample ass cheeks.
Sierra’s skin tone to me was just so intoxicating, as I ran my hands up and down her thighs I just stared at her in amazement. I must have paused for a moment, because she had looked back at me and asked if I was ok. I just smiled at her and continued to run my hands up and down her legs. Whenever I would get near her cheeks she would slightly lift her hips up and I would hear a faint moan. After a couple times she began to spread her legs inviting me to go further. I climbed over her legs and began to kneed her cheeks in my hands and her moans picked up. I continued to sensually massage her ass and lower back before I laid over her and pressed my body to hers. I was careful with her new hair and moved it to the side and began to kiss her shoulder and the base of her neck. Sierra whispered “oh baby don’t stop” and ground her ass into my cock. I continued to kiss her neck, shoulders, and sucked on her earlobe as we ground our hips together.
In a whisper I asked her what she wanted, and she wantonly begged me to eat her pussy. I seductively slid and kissed my way back down her body. When I reached her ass I pushed her left leg up and pulled her cock out from under her to where it was behind her. I kissed the head of cock and up her shaft to her balls before I reached her pussy. Her cock was leaking like broken faucet, and her hips were bucking, begging for me to bury my tongue in her pussy. As she arched her back and lifted her ass, her cheeks naturally spread open for me and I buried my tongue into her her tight little pussy. Immediately, I heard her gasp and say “oh fuck baby, don’t stop” I had no plans to. I sucked and kissed and tongued her pussy until she was bucking uncontrollably on my tongue. After about 10 minutes of this she reached back and grabbed my head and pulled it into her, begging me to make her cum. I pulled her hand off my head and within a breath I had slid up her body and buried my cock all the way into her.
I could see her eyes roll back and she stopped breathing for a second before she gasped for air and thrusted back into me. Our bodies were locked together and as I ground my cock into her pussy, she couldn’t do anything but gasp for air. I ground my cock into her as hard as I could, I wanted her to orgasm like a female, hands free, and I wanted to breed her at the same time.
A couple minutes of this and I could feel the urges coming, I was getting close. Sierra was almost incoherent but I could hear her and feel her tighten up and to start to spasm. I continued pumping in and out of her for a few more moments before I wrapped my arms around her and filled her pussy with a massive load.
As I lay on top of her catching my breath, Sierra was silent and her body was shaking underneath me. I slid back down her body, looking at the results of our lust, and her pussy was leaking cum, and the bed was covered in come from her orgasm. I stood up and went to the bathroom to get a towel to clean up our mess. Sierra hadn’t moved when I got back so I just started wiping her body down and then her cock and ass, before wiping myself down.
Sierra finally showed some kind of life and reached back and took my hand. I laid down next to her and she crawled up onto my chest and passed out. The alarm went off at 630 the next morning and Sierra hadn’t moved all night.
I slid out from under her as quietly as I could and got in the shower. As I was washing my hair, I heard the curtain open and felt Sierra’s hands on my stomach. As I finished washing my hair, Sierra just ran her hands over my chest and stomach. Once I rinsed my head off. She just leaned in and held me. I wrapped my arms around her neck and shoulders for a moment and held her tight. I leaned down and kissed her deep and long. When I pulled away, I smiled at her and she asked me what I was smiling about, and I chuckled and said your new hair is wet and began laughing. She wasn’t too happy at first but the she must have figured it was already wet and she leaned back into kiss me. The feelings between us were so thick it was palatable. She already had confessed to be in love with me, and I don’t think I was too far away from saying it back.
Another week went by and it was back to life as usual. Sierra went back and forth from her place to mine a few times during the week and she even cooked for all my coworkers. But, the memory of what happened in St. Augustine was forefront in my brain.
Sierra – part 9 – the end of us
Sierra and I have been together for almost 10 weeks at this point and life was amazing with her. We had settled into each other and we were enjoying our relationship. We had an amazing sex life as well. Both of us in our early 20’s what did you expect, lol. I could tell Sierra had let her ex’s memory fade to the back of her brain. She seemed like she was letting go more and enjoying us. But, I couldn’t. After the night with Tim and Amy, I just had a gut feeling that something bad was coming, I just didn’t want to let her see that fear. I remember it being a Wednesday at dinner time, and Sierra asking me if I thought it would be ok to go see her parents in Orlando, since it had been about a month or so since the last time. She said that she had been talking to her mom for a week or so and had mentioned me. First, I would never stand between her and her family but I knew why she was asking, so I asked her if she wanted me to go with her. Her face immediately looked surprised and her eyes got big. I just looked at her and said that I didn’t have to, it was just an idea. She began to tear up and climbed onto my lap, straddling me. In a look of disbelief she asked me if I was serious. I said why not, it’s been two months, we are practically living together. She squealed and hugged my neck so tight I thought I was going to choke. She was like a teenage girl for the rest of the night, all excited and nervous, it was funny to watch. For the next two days she was so nervous about me meeting her family that it was funny. She said mom was excited and dad was going to be overprotective. I just told her that I understood.
Friday night, Sierra tossed and turned all night, excited and nervous. So much so that she woke me up at about 6am, rubbing my cock. She told me to get up and shower and clean up. I took that as she was horny. I looked at her and she gave me the look of do what I tell you. She pushed me out of the bed and said hurry because we weren’t going to have sex all weekend in her parent’s house. I did as I was told and when I got out of the shower, Sierra wasn’t in the bed and my black box of toys was out on the floor. I found Sierra on a blanket on the living room floor with the patio curtains all the way open, which didn’t bother me being on the 2nd floor.
I walked over to her and stood above her, and she began to lick my balls and cock. As she did I could see the double ended dildo and a bottle of lube next to her. Her lips around my cock and balls felt amazing. While she sucked my cock she began squeezing and playing with my ass.
I kneeled in front of her and laid her down underneath me. I leaned down and kissed her, our tongues danced and our hands explored each other lustfully. I could feel her cock touching my hole and it was as hard as stone. I reached over to get the lube and she said to wait. She pushed me back to where my ass was between her thighs and our cocks were rubbing on each other. As she opened the bottle of lube up I put our cocks together and stroked them. Sierra was very liberal with the application of the lube. She squirted it all over our cocks and lower bodies. We rubbed it into each other’s ass and all over our cocks. I lifted my hips in anticipation of her massive cock but she just told me to wait. She then lifted one leg over one of mine and we were scissored together . She reached over to the double ended dildo and drenched it in lube.
Sierra told me to lay back and lift my leg, I did as I was told and she began to finger my hole rubbing lube all into me. A moment later she pressed the head of the dildo into my ass causing me to gasp. This dildo was 18 inches overall length with a divider in the middle and about as round as red bull can. Sierra slowly worked it in and out of my tight hole until I was begging her to put it in. On command she pushed it all the way to the splitter into me, I let out an “oh fuck” and she began sliding it in and out of my hole. A moment later, she slid her ass close to mine and I repeated the process on her that she did to me, and slid the other end of the dildo into her.
We both laid back and ground our asses together before we started to pull apart and push back together again. Sierra reached down and took both of our cocks and held them together as we rode the dildo together. After a few minutes she pulled the dildo out and turned over onto her knees, I did the same and reinserted the dildo back into and we fucked each other doggy style for over 10 minutes, both of us were sweating and moaning, precum leaking everywhere to. Before I knew what was happening, Sierra pulled the dildo out of my ass and shoved her cock into me. She still had her end of it in her and put the other end between her feet to hold it, so she could fuck me and get fucked at the same time. This didn’t take her long, she grabbed my hip in one hand and my shoulder with the other, arching my back and fucking me like a wild man.
The arch in my back changed the angle of her massive cock and it was rubbing my prostate like crazy. A moment later it hit me, I was exploding hands free, it was such an extreme orgasm it caused me to get light headed. As I was cumming, Sierra was filling my boi pussy full of her cum. By the time we had finished cumming she had pushed me down and was laying on top of me, her cock still in me and the dildo still in her. I rolled out from under her and as her cock came out of me, her cum flooded out as well. We lay next to each other for a moment, me on my back and her face down. I looked down and could see the dildo still in her and I sat up. When I touched the dildo she begged me to be gentle taking it out. I straddled her legs and reached down and took the dildo and began slowly sliding it in and out of her pussy again. Her body and her mouth contradicted each other. Her ass rose up for more but her mouth begged me to stop. I kept sliding it in and out of her. I pushed her left knee up to her chest and pulled her limp cock back from under her belly. As I fucked her tender hole with the dildo, I massaged the head of her cock making her twitch uncontrollably begging me to stop. I told her to lay there and enjoy it. I picked up the pace in which I was fucking her and she began to moan heavily now and thrust her hips up each time I pushed in to meet the dildo. Watching this was making my cock hard again and after a few minutes I took the dildo out and slid my cock all the way into her. With my legs on each side of her ass, she kept her hips arched upward and met me stroke for stroke. I fucked her pussy as hard as I could until I filled it with my second load of the morning.
Both of us exhausted, covered in sweat and filled with cum we didn’t move for what seemed like forever. I eventually lay next to her on the floor and we both passed out. About an hour later, I woke up to Sierra kissing my cheek and her playing with my nipples. I just looked at her and she giggled at me and said we are late. I looked at the clock and it said 817am. We wanted to be on the road by 8am. We both jumped up and took a shower, loaded up the car and began the hour trip to her parents.
The entire trip was filled with anxiety, both for me meeting her parents and the fact that we didn’t know what her ex was doing or where he was. Sierra looked amazing as usual and was chatty all the way to her parents’ house; her nerves were getting to her. I could also tell as we got closer that her radar was on full tilt. I could see her scanning the each street we went by in her parent’s neighborhood, and we even circled the block a couple times to make sure her ex wasn’t watching.
When we finally arrived at her parents’ house, her mom met us outside and her father just stood on the patio measuring me up. I could see that Sierra looked just like her mom, and her mom was just as sexy. Her father was about my height 6’3 and a little heavier than me. Sierra’s looks came from her mother but her skin tone definitely came from her father. I asked her father if I could come up on the patio and he nodded, I reached out and offered my hand to him and introduced myself. At first he didn’t shake my hand, he just glared at me. Then I heard Sierra fuss at him and tell him to be nice and shake my hand. He shook my hand and then asked us to come inside. The first hour was awkward but pleasant, until her father asked me to join him out back. I did as I was asked. When we got into the back yard we sat a small round patio table with umbrella and a few chairs. He offered me a beer and said he wanted to talk to me alone.
The conversation went from him asking me questions about my past to Sierra, or in his case Sam. I never knew her birth name until then, but then again I never asked. Her dad asked me what I knew about her and her past. I told him what I knew and he just nodded and leaned back in his chair. He leaned back to me and in a dead serious look on his face he asked me if her ex ever found out where she was, what I was willing to do to protect her. I leaned toward him and with our faces a foot apart I told him anything. He stared at me and in all seriousness he asked would you give her up to protect her? I never considered that an issue. I sat back for a moment, took a swig of the beer and leaned back in and said yes, if that is what it took for her to be safe. He leaned back into his chair and stared off into the sky for a minute and took a swig of his beer, before he leaned back to me. I sat waiting patiently, but what he said took me back. He told me that he and his wife have an exit strategy to get Sierra out of the state if he ever found her. An open ticket at Melbourne Airport to a location that he wouldn’t tell me, and that if the day came, that I would have to make her pack and get on the plane. He looked me dead in the eyes and made me promise him that I would do it. He said her ex was crazy and came around at least once a week watching the house and that he was just there in the neighborhood two days prior. I looked at him nervously and he said that we could put my car in the garage and Sierra and I could sleep in the pool house for the weekend. I looked across the backyard and could see a small 10 by 20 foot pool house and the entire backyard was surrounded by an 8 foot privacy fence.
Just then I could feel eyes watching me and I glanced left and could see Sierra and her mom peeking out the kitchen window at us. They were giggling, and I told her dad that we had an audience, and he said that they were just trying to see if I was going to kill you, and he chuckled. I looked back at him and said that is easier said than done. He tilted his head to one side and saw that I was serious and he stood up and extended his hand to me. It was a gentleman’s understanding of what needed to be done. We then tilted our beer back and finished them off before we unloaded the car and put it in the garage.
Sierra was attached to my hip as I carried our suitcase to the pool house. She was desperate to find out what her father said to me and what I said back to get a legit handshake from him. As we entered the pool house, it looked like a hotel suite inside. It had a small kitchenette, queen bed, a love seat and ¾ bath. It was actually really nice. I placed our suitcase on the bed and Sierra grabbed my arm and turned me to her and playfully hit my chest asking me again about what her father said to me.
I told her about our conversation, minus the information about her ex being in the neighborhood two days ago. Sierra looked shocked about her parents exit strategy for her and didn’t know what to think about it. She looked at me and said that would mean us not being together and I looked at her and held her face in my hands and told her that if that is what it took for her to be safe than that is what would need to be done. She hugged me tight and I kissed the top of her head. As we unpacked, we heard her mom yell for us to join them by the pool for drinks and a swim.
I glanced out the window and could see her parents walking out onto the patio, her mom in a bikini and her dad in regular swim trunks. I glanced at Sierra and told her I see where you get your figure from; damn your mom sexy, lol and that got me a punch on the arm. Sierra helped me undress and stroked my cock a few times. I reached into the drawer and pulled out the blue thong she bought me and she gasped and told me heck no, not in front of my father. I laughed and grabbed my trunks. As I got dressed she was undressing and I decided to tease her a little bit. As she bent over to take her panties off I bit her on the ass cheek and she let out a little squeal and she smacked me again and told me to behave before kissing me. We walked outside and she grabbed my hand and we walked around the pool to where her parents were and sat down. Sierra sat next to her mom in the lounger and I sat with her dad back at the patio table.
As her father stood back up to get the cooler with the drinks in it, the sun caught the imprint of his cock on the front of his trunks; I thought to myself that size definitely runs in the family. As her father was in the house I could overhear her mom trying to whisper to her, that no wonder she liked me, I was young and very in shape and handsome. Sierra told her mom to behave and they chuckled. For the next 30 minutes or so the ladies sat next to each other trying to whisper back and forth and giggling. Her father and I both knew they were talking about me and we just rolled ours eyes and made small talk. I found out that we were both in the Army and served in combat. I could tell this knowledge made him feel more at ease with me.
After a while, he looked at me and quietly asked if I knew that he didn’t approve of Sierra’s choice to live as a female but he has learned to accept it and seeing her with me was hard but he was happy that she was happy. I admitted to him that I wasn’t looking for this type of relationship when I met her but she is an amazing person and I cared for her deeply. He looked at me inquisitively and I told him that I had experimented prior to being with her but never expected this kind of relationship, and he gave me that look of understanding.
We talked and swam the rest of the morning and had a few more drinks before a light lunch. Even with Sierra attached to my hip in the pool, I couldn’t take my eyes of her mom’s figure. She was in her early 50’s, 5’4 or 5’5 maybe 130-140 pounds perky c-cup breasts, flat stomach and ass that just stood up. Her mom’s skin color was a solid mocha color, nowhere near as dark as her husband or Sierra.
Every once in a while I would get caught looking a little too long at her mom and Sierra would pinch me under the water and tell me to behave. The feel of Sierra silky soft skin against mine made me horny as hell and I had a raging hard on under to water. Sierra knew it and turned her back to me and I wrapped my arms around her as we floated near the wall of the pool, my cock lying right between her cheeks, just as it was a few hours before.
Her mom watched us for a moment and told us that we looked good together and was happy for us. We both said thank you, and I told her mom that Sierra was very special to me and she was an amazing person. Her mom awed and did the pouty lips face and swam over to us and gave us a hug. When she did she pushed her chest against my right arm and her left arm went a little low against my waist. This was an awkward situation, my rock hard cock was in Sierra’s ass cheeks and her mom was rubbing her tits on my arm as she tried to grope me under the water. I wasn’t quite sure what to make of it so, I just let it happen. Then her mom in a very energetic way leaned back and said it was lunchtime and pushed away from us. Sierra got out of the pool first and then I climbed out, trying to keep my hard on out of sight from her parents. We went back into the pool house and as we undressed Sierra looked at my situation and dropped to her knees and gave me an amazing blow job and swallowed my entire load, which at the time wasn’t a lot after our morning escapades, but it did its job and I could face her parents again comfortably. I threw on the clothes that I came in and Sierra put a dress back on and we went back into the main house.
Her mom was still in her bikini and her dad left his trunks on and threw a t-shirt on. As her mom made blt’s for us, I couldn’t help but get a better look at her. I didn’t stare but glanced intently numerous times. I could see that her pussy was clean shaven and she had nice thick lips. Her nipples appeared to be about the same size as Sierra’s which I loved. As we ate lunch we made small talk and her mom kept glancing at my legs and I assume crotch as well. Non-saliently I opened my legs a little wider from time to time to tease her, two can play this game.
I wanted her dad to see how much Sierra and I cared for each other so Sierra and I sat close to each other and would wrap our arms around each other and show innocent forms of affection to each other.
After lunch Sierra and I went back to the pool house and napped. I woke up first, and went out to the pool area. As I was sitting there I could hear the sounds of her mom and dad fucking inside the house. I don’t know how long they had been going at it but from when I heard it, to hearing him finish it was about 10 minutes. It was a few minutes later that her mom came outside still in her bikini and very sweaty. I gave her a devilish grin and she lay down on the lounger and slightly spread her legs. I could see that the crotch of her bikini was drenched through with her husband’s creampie and her juices to mix. We never said anything to each other but the sexual tension was becoming palatable. Sierra joined us a little while later in her bikini and we all just relaxed and drank the rest of the afternoon. Her mom continued to be a tease all afternoon, which was funny to me, but Sierra was getting a little annoyed with it. I had to reassure her that everything was fine a couple times. Around 4pm her mom suggested that we go out for a steak dinner, and that made Sierra nervous. I gripped her hand tight and told her she was safe. Her mom noticed this and told us that we were going to Kissimmee for dinner and that she would be safe with her dad and me protecting her.
As we went back into the pool house, Sierra was still visibly nervous and I hugged her and kissed her deeply, telling her that she was safe. To distract her I told her that I had bought her a new dress, and it worked. She got all giddy and begged me to see it. I had hid it in the stack of my clothes. I told her to close her eyes and to put her arms out to the side. She did as I asked but she was fidgeting like an excited 2 year old. I chuckled at her as I took her bikini off her and gave her cock a quick stroke, that got an “oh fuck” out of her and then I pinched her left nipple and she told me to behave. I took a second and just stared her beautiful body before I told her to put her hands above her head and no peaking. I then pulled out this silk, spaghetti strap dress with flowers on it and slid it over her head. The feel of the silk on her skin made her gasp and I could see her nipples get instantly hard. I told her to keep her eyes closed and I turned her toward the mirror and told her to open her eyes. The look on her face was priceless, her mouth just fell open and nothing came out of it. Then I could see her eyes swell up with tears and she just said it was amazing and beautiful. As I stood behind her, I pulled her hair back off her neck and kissed her shoulder and whispered to her that I would do anything for the woman I loved.
A look of disbelief came across her face and she turned to me shaking and just asked “really?” I said I couldn’t hold it in anymore. I had to tell her that I was falling in love with her. It didn’t really hit me until her father asked me if I could let her go to keep her safe. When he asked me that, I knew the answer. I held her and asked her if it was so hard to believe that I did, and with tears in her eyes she just shook her head. I told her that she was an amazing person and that anyone would be lucky to be with her, but it was me that was lucky to have met her and for her to let me into her life was special. She began to cry even harder, she said that these were happy tears as I wiped them from her face. I told her if they happy tears then stop crying and tell me what you think of the dress. She giggled and said it was amazing and then asked me how I could afford it. I told her that I saved for a few weeks and bought it for the right occasion. She held my face in her hands and kissed me. I told her to get her butt in gear and get dolled up for dinner and smacked her on her ass. She stood in the mirror for another moment, looking at her dress from all angles. She was stunning. She looked at me and said that she was gonna have to tie up tonight or she would really show off.
When I finished getting dressed I walked over to the main house to get Sierra a glass of wine, her mom was walking around naked trying to get ready and didn’t know I had come in the house. I cleared my throat and her mom jumped and said “oh shit” I apologized for startling her. She then realized that she was naked. Her husband was upstairs, and she just gave me a devilish smile and put her hands on her hips and asked what I thought. I told her that I see where Sierra gets her looks, and that she looked delicious, as I returned the devilish smile. Her body was amazing for 50 plus. Her pussy lips were thick and clean shaven, her nipples were as I thought, just like Sierra’s. She turned her ass to me, which I had been staring at all day but fuck she was sexy. I grabbed the wine and some glasses and gave her another look and smile and returned to the pool house.
We rode in her father’s Cadillac SUV on the way to dinner, which was great due to the blacked out back windows. Sierra looked absolutely stunning in her dress and her mom wore a similar dress, neither wore a bra. Her dad and I wore dress pants and a polo shirt with some slip on dock shoes.
Dinner was great. We sat in the corner booth, which is one of those half circle ones. Somehow I got pushed to the middle next to Sierra’s mom and Sierra and her dad sat on the outside. The ambience was amazing, cozy and romantic with low lighting. Sierra had her hand on my right thigh most of the night and would brush my cock with the back of her hand when her dad wasn’t paying attention. What Sierra didn’t see was that I put the cock ring and splitter on with the blue panties under my dress pants. When her dad got up to use the restroom, Sierra sneaked a grope on my cock and felt it restricted and her eyes got big when she looked at me. I just gave her a devilish smile and went back to eating my dinner and talking to her mom. While her father was away we were laughing about something and her mom put her hand on my thigh and gently squeezed. Not sure what was happening, I didn’t stop her. I leaned back in the booth pretending to take a breath from eating and slid my hand onto Sierra’s thigh and softly ran it up and down her silky thigh for a moment. I wasn’t sure what was happening with her mom though, maybe it was the alcohol, but she kept her hand on my leg for a moment and when Sierra lifted her hand up, her mom brushed my cock with the back of her hand. I gave her a quick glance and she smiled at me. Not soon enough her dad returned to the table, with a different look on his face. He didn’t have to say anything to me, I knew. We finished our meal and didn’t stay for desert. On the ride back to the house her dad was quiet while the girls chatted away, I could see him checking his mirrors and looking in the rear view at me several times. It wasn’t until we got to the house and the girls went their separate ways that he said one of her ex’s friends was in the back of the restaurant. I told him that we would stay the night and leave after lunch, so Sierra wouldn’t freak out. Her ex had no idea who I was or where I lived so the plan would be to go to my house when we got back to Cocoa Beach. I had to act like there was nothing wrong for the rest of the evening.
As we said goodnight her mom gave me a little longer hug than maybe appropriate and grinned at me. Sierra and I went back to the pool house, and as soon as we were in the door she unzipped my pants and yanked them off asking me to explain why I was wearing my sub gear. I smiled at her and just shrugged my shoulders. She reached under her dress and untied her cock and let out a groan when it fell free. She looked at me with that devilish smile and told me to go clean up. I knew what that meant and did as I was commanded. A few minutes later when I came out of the bathroom, Sierra was standing there in her panties, which didn’t restrain that massive cock of hers to well. The lights were on and the curtains open in the pool house. She looked back to see what I was looking at and she said not to worry that her parent’s bedroom was on the front side of the house and couldn’t see us. Just then I heard a distance rumble of thunder and some sprinkling of rain on the windows. Sierra told me to drop my panties and get in the pool. As I walked outside to the pool my cock was hard as it could be. I knew what Sierra was about to do to me, but I was wondering what her mom was doing. I wondered if she was trying to sneak a peek. We floated in the pool for a moment before she pinned me to the wall and kissed me deeply. Her breast’s, firm but soft, were pressing against my chest and her cock pressed between us. My cock was gently resting between her cheeks, but she wasn’t having it tonight. She spread my legs and slid between them. At first my cock was between her tits as I floated in front of her. Then she pulled my hips down and like missile lock her cock found my hole the first time. I knew this was going to hurt, we had no lube and submerged in water, but she pushed anyway. I let out a silent scream and begged her to wait. She just smiled at me and pushed again. This time her massive cock slid into me about half way in and I gasped quietly. Then she kissed me and finished pushing into me. She just held me and held her cock still, waiting for me to adjust to it. After a minute or so, I began to slowly move my hips up and down it; this gave her permission to start sliding in and out of me. Floating in the water gave her full control of me, and she used it to slide me back and forth on her cock instead of her thrusting. My arms were holding my head above water on the edge of the pool as she slowly fucked my ass. As she fucked me I reached between us and played with her nipples, pulling and twisting them, making them even harder than they were. This extra arousal made her pump me even harder, I was moaning and grunting as quietly as I could as Sierra continued fucking me. At one point I thought I saw her mom in the upstairs window but when I looked back there was no one there. After about 15-20 minutes, Sierra put her hand behind my neck and pulled me to her as she buried her cock as far as she could into me. I couldn’t make a noise; I just had my mouth open in pleasure as I felt her cock twitch inside of me. She held there for a moment before she made several short strokes in and out of me. I leaned forward and kissed her hard and passionately, and her cock slid out of me. We stood there for a moment before I picked her up and carried her to the bed. We laid there kissing and caressing each other until she fell asleep. After I tucked her in my brain went to full protection mode. I quietly packed our bags and left out a set of clothes for each of us to wear and packed everything. I left my restrictive device on and slid my blue panties back on while I packed. Her cum would occasionally run down my leg and I would have to wipe it up. Never thought I could do it 3 times in one day but it was amazing.
After finished packing I check for any lights on in the main house and saw none. I turned off all the lights in the pool house and went outside to check the fence gates to make sure they were locked. As I went to the gate on the garage side of the house, I saw a figure in the shadows sneaking around to the opposite side of the house. He obviously didn’t see me or he would have ran. Now anyone watching would have laughed but, I very quietly snuck around the front of the house only wearing my panties and a restrictive device on my cock and balls. As I came around the corner, I could see a male figure standing next to the fence with a camera. I was able to sneak up behind him and knock him down. I told him if he made a sound I would dislocate his shoulder. I asked him who he was and he said a private detective. I asked him who he worked for and he wouldn’t tell me, so I dislocated his finger and covered his mouth before he could scream. While I kneeled above him with his arm bent straight back, I began to pat him down and check for weapons or anything else I could find. I found 3 rolls of spent film, his wallet, notebook and pen, and some business cards. I tossed the film rolls over the fence and took one of his business cards. I grabbed his camera and pulled the film out of it, exposing it all. As he laid there crying in pain, I told him that if I ever saw him or his no named client again, I wouldn’t stop at a finger. Then I realized I was only kneeling there in my panties, so I pulled my cock out and his eyes got huge, and I said why don’t we just make sure you never come around this family again right now. He begged me to let him go. I messed with him for another minute before he said he would tell his client he was done with him. Before I let him up I reiterated my commands to leave the family alone by resetting his pinky finger back into place. He let out a silent scream and lay on the ground for a moment before he got up and left. He ran to his car and sped away. As I came back around the corner of the house, I locked the gate behind me and double checked the street. As I entered the backyard, I saw Sierra’s mom lying on the lounger with her legs spread. I snuck up on her and she was rubbing her clit moaning. I stepped in front of her and began stroking my cock. Sierra came in me but I didn’t cum and I was swollen. Her mom finally opened her eyes and gasped and then gasped again seeing my cock in full form. She said quietly that she watched Sierra fuck me and she had just finished getting fucked by her husband and she was still very horny. I could see in the ambient light that her pussy was extremely creamy and her lips were very puffy.
She sat up and took my cock in her hand and began stroking me. I was so horny that I told her to stop that I was about to cum all over her. I stepped back and she looked upset. She then asked me if I was a sub to Sierra and I told her that sometimes I was, like tonight. She said good, then kneel down on the grass. I looked at her inquisitively and she smacked the head of my cock hard and said kneel again but in a commanding voice. I took the towel and laid it on the concrete and kneeled on it. She then stood up and grabbed my head and pulled it into her pussy. She told me to eat her husband’s creampie and to make her cum. I reached around her with both hands and grabbed her ass cheeks and pushed my face deep into her pussy. Her husband’s cum was running out of her and I eagerly licked it up burying my tongue as far as I could into her loose pussy. I sucked her lips and her clit with determination. All she could do is hold onto my head with both hands and moan. Her legs were shaking almost violently, but I was holding her up by her ass cheeks. When I sucked all her husband’s cum out of her, I attacked her swollen clit. I sucked on it and swirled my tongue around it until she squirted all over my face and chest. I was loving it. She pushed my head away and leaned down to kiss me. We kissed passionately, like Sierra and I did. As we kissed she pulled me up and grabbed my cock again. My balls were swollen and she pulled the ring off of them and took my cock to the back of her throat. Fuck what was happening, I thought to myself.
It didn’t take long for the sensation to build in my balls. As she was sucking me she began massaging my balls and running her fingers over my ass. I was still sore from Sierra, but I went with it. A moment later she was circling my hole with 2 fingers. She was using Sierra’s cum as lube to push her fingers into me. It only took a few seconds for me to explode into her mouth. I came so hard I became dizzy, and had to hold onto her for balance. She sucked me dry and stood up kissing me again.
We both looked at each other in a sort of shock and looked around but didn’t see anyone watching. We got into the pool quietly and rinsed off. I massaged her breasts for a little while and played with her clit again, commenting on how I loved her thick pussy lips. She said she wanted to fuck me all day, but had her husband do it, that’s when I saw her earlier today with cum filled panties. She said she knew I was interested with the smile I gave her. As she talked to me I slid two fingers into her pussy and pushed on her clit with the palm of my hand causing her to moan. I finger fucked her vigorously until she buried her face in my chest and I felt her hips buck back and forth involuntarily. When her bodied stopped moving I slid my fingers out of her and flicked her clit one more time causing her to pull away from me. I kissed her again and told her we need to separate before we got caught. She nodded and we went our separate ways for the night. Before I went back into the pool house I collected my cock ring and panties as well as the rolls of film and business card. I hid the film and card where Sierra wouldn’t see it and went to bed.
The next morning, Sierra was hungover and moving slowly. When she got up she saw the suitcases already packed and asked what happened. I just told her that I packed after she passed out. I helped her into the shower and washed her gently and helped her get dressed before we went over to the main house. I wasn’t sure what I was going to see when I went over there after what happened. But, it was safe, her mom was in a light dress and her dad was in a pleasant mood and just wearing some gym shorts. I could tell he had no underwear on cause his huge cock was swinging freely. We ate a light breakfast and as Sierra and her mom talked, I asked her dad to help me in the pool house.
As soon as the door closed he had an intense look on his face. I opened the drawer and pulled out the film and business card. He looked at me and asked what it was. I told him that I caught a guy, and handed him the business card, taking pics over the fence. As dark as this man was I could see him turn red in anger. I told him to calm down because I broke his finger and almost made him suck my cock, and chuckled. Her dad stepped back and let out a deep laugh. I told him that the guy wouldn’t give up his client’s name, but we both knew who it was. I told her dad that I scared him to the point of making him quit the case. Her dad got that very serious look on his face again and put his hand on my shoulder. His eyes began to tear up and he said that we both knew what had to be done, and that meant sending Sierra somewhere safe. He refused to tell me but we set a plan in place for 10 days out. We had to break it to Sierra the right way.
Sierra and I left just before lunch and unintended I was almost silent on the way home. When we got back to my place, Sierra grabbed my arm before we got out of the car and asked me what she did wrong that I wasn’t talking to her. I did my best to reassure her that she did nothing wrong, I just had a lot on my mind. When we got inside, she was like an insecure teenager thinking that I was mad at her. I held her face in my hands and told her that I loved her and she did absolutely nothing wrong. I knew I needed to lighten up my mood before she figured it out. So we started talking about the weekend, and I asked her if her mom said anything to her about me.
Sierra giggled and told me that her mom thought I was sexy and we looked good together. She also said that her dad whispered to her that he liked me and that he was proud of her and he loved her. This made Sierra tear up and she said that is all she ever wanted to hear from him. I was sitting in the dining room chair when Sierra walked over to me and sat on my lap. She said that whatever her dad and I talked about worked. I think it was the Army thing I said, not sure what else it could be, I said jokingly, while I started tickling her. We ended up on the floor wrestling around for a few minutes when I ended up on top and we kissed. My face went from playful to serious and I kissed her passionately. She reached up and held my face in her hands and asked what that was for. I just looked at her and said do I need a reason to kiss the woman I loved, and almost immediately there were tears in her eyes again. I sat up and asked what she was crying for now and she hit me on the arm, and chuckled under tears.
After dinner, I took her home and dropped her off, so I could get ready for work the next day. My mind was racing; I knew what had to be done but didn’t want to do it. Before I pulled out of her complex, I circled the parking lot several times looking for anything out of the ordinary and didn’t see anything. I didn’t sleep well that night; it was the first night in about 2 weeks that Sierra wasn’t with me. I called her before I left for work the next morning to check on her and she was fine and told me that she would bring me lunch today. When she got to my work she was wearing the silk dress I bought her. I almost fell out of my chair, and both of my coworkers said “fuck” at the same time and loud enough for her to hear it. Sierra giggled and handed me my lunch, salmon and asparagus. As I walked around my coworkers I purposely bumped into them and chuckling under my breath. I remember thinking to myself, how in the fuck did I get so lucky. I told her she looked amazing, and asked her what she was doing for the afternoon. She said she wasn’t sure. So I asked her if she wanted a massage and facial or hair and nails. She started bouncing up and down all excited forgetting that she wasn’t wearing a bra. I could see my coworkers staring at her, and I glanced sideways at them before they stopped staring. Sierra, decided on a massage and facial so I gave her some money for the afternoon. As soon as she left my coworkers got up and ran around the other side of the counter, commenting on Sierra’s tits and ass, and how lucky I was. I just laughed to myself, and thought only if they knew she had a 9 inch cock to, lol.
After work that evening I went to the gym and was chatting with the manager before my workout. He said he hadn’t seen me in a few days and asked if I was alright. I told him about meeting Sierra’s parents and what not. Before, I went into the locker room the manager warned me about some new members. A group of roid heads as he called them. He said 6 or 7 guys signed up over the weekend and they were competition bodybuilders and strongman competitors, and that when they were in the gym they can be a little intimidating. I thanked him and went and did my work out. As I was finishing my steam room session, one of these “roid heads” walked in butt naked. This guy had to be 6’2 -6’3 and 265-270 solid muscle. Since he was naked I did have to check him out. He wasn’t a bad looking guy, his body was clean shaven and tanned solid from head to toe, and his cock limp was only 2-3 inches and looked skinny. He sat on the end as I was on the right side. He just sat there with his eyes closed until I started moving around. Out of the corner of my eye, I could see him look at me up and down when I got up, I wasn’t sure what to make of it so I just left.
I was almost expecting Sierra to be there when I got home but she wasn’t, she had left a message for me telling me she was chilling at her house and thanked me for the spoiling today. On Wednesday, she came by my work again and brought me lunch. She looked amazing as usual, I told her I missed her yesterday and she assured me that I wouldn’t miss her tonight. She kissed me and left.
When I got home from the gym, she was at my apartment waiting for me in a nice dress again. I asked her what’s up and she said she wanted to go to the restaurant that I took her to the first night we went out. I showered up and when I got out of the shower I had a new pair of panties on the bed, cherry red, and it was another thong. There was also a set of tan linen pants and shirt laying there as well along with a set of new sandals. I looked at her and she said daddy gave me some money and you are always buying me things, I thought it would be my turn. I smiled and thanked her. Subconsciously I was screaming because I knew what was going to have to happen in the next few days.
The outfit fit perfect and if you looked really hard you could see my red panties under the pants. She smiled at me and then it turned into a devilish smile which I have seen before. I looked at her and asked her what else am I wearing tonight? She smiled and pulled out a leather cock ring with snaps and an even large spreader. I dropped my pants and pulled my panties to one side and she strapped it on me as tight as it would go. The pressure was really intense. My balls were stretched over and inch and they were starting to swell slightly. I pull my panties back over my cock and pulled my pants up. It looked like I had a massive cock. I lifted Sierra’s dress and her cock was freshly shaven and strapped to the inside of her left leg.
When we arrived at the restaurant the host took us to a table in the back and the waiter immediately sat a Jack Daniels and Coke down for me and glass of wine for Sierra. I looked at her and she just said “mom.” I chuckled to myself remember the night in the pool. I said to Sierra that your folks really liked me huh? She said that her mom really did but her dad didn’t say much. I chuckled and she asked me what was funny. I just laughed again and reminded her of how her mom was flirting with me, I found it funny. Sierra giggled and said that you may, but I didn’t. I just chuckled and the waiter returned a moment later and took our order. Sierra slid closer to me in the booth and kissed me. I looked around and there was no one in this part of the restaurant yet, which was strange but I went with it. Sierra slid her hand under my shirt and started rubbing my chest and playing with my nipples, which in turn made my cock hard. I could see the waiter, a young guy about our age, definitely gay peeking around the corner watching us make out. I glanced over at him and smiled. He shyly put his head down and took a step back behind the wall. I whispered to Sierra that we had an audience. She glanced up at me and I told her the waiter was watching us. She smiled, and kissed me again while she stroked my cock through my pants. I could see him peeking again and just staring at us. I smiled and this time he smiled back. A few minutes went by and I could see the waiter turn his head back to look at something and I told Sierra to sit up. A moment later our food arrived. The young slim waiter brought our food and as he walked away, Sierra said he had a cute tiny ass, and giggled. I looked at her and said I bet he has no idea about you and he is a bottom. She saw the look in my eyes and she said not tonight, that tonight was for us. I said ok, but we can still give him a little sneak peek, and that got a grin from her. After dinner, the entire restaurant was a little slow and we still had our side to ourselves. So we just relaxed and had a few more drinks and made out some more. As we made out I could see the waiter peeking again. He had a clear view of both of us and could see Sierra stroking my cock that she had pulled out of my pants now. The waiter’s eyes were glued to my cock and the spreader around my balls. Just then I leaned into Sierra and ran my hand up her leg and she moaned into my mouth. The waiter had no idea what was about to happen, he had no idea that Sierra was trans. I pulled her dress up slightly and ran my hand up her cock and she let out a soft moan. Her cock was rock hard but still tied up.
To the waiter, in the dimmed restaurant, and Sierra’s ebony skin it must have not registered that it was a cock I was stroking and not a thigh. I stroked it for another minute and told her that I was going to untie her. She buried her face into my neck and moaned as I untied her massive cock. When I did, it popped up almost vertical and the waiter almost fell over in shock. I smiled at him and continued to stroke her cock as we kissed. I could see the waiter rubbing his own little cock through his work pants. I could see the manager sitting down at the bar with his back to us, so I knew the waiter wouldn’t get caught watching us. As I kept a careful watch on the manager and other employees, I waived the waiter over and told him to taste her.
Sierra looked up at me kind of in shock, but she went with it. The waiter kneeled down in front of Sierra and I could see him shaking with nerves. I pointed her cock toward his mouth and he just leaned forward and began kissing the head of her cock and licking around the crown of it. Sierra squeezed my arm and then began stroking her own cock while the waiter did his best to suck her massive cock; mostly he just ran his tongue all over it and kissed it up and down. This went on for a few minutes and Sierra was really getting worked up. The excitement of this happening in full view of the public in a restaurant and his soft little mouth and tongue had her close to cumming already. Sierra’s grip on my arm was getting tighter, and I whispered to the waiter you either stop now or take it all. He looked at me and without any complaints he sucked the head of her cock in his mouth and did the best he could to make her cum. I could see his tongue swirling around the crown of her head and her grip kept getting tighter on my arm. A moment later her other hand reached down and grabbed the back of his head. A feeling I felt many times, and I knew she was flooding him with her hot cum. The soft grunts and involuntary bucking of her hips told me that it was intense. The waiter was stroking and sucking every drop out of her until she was done. The waiter released the head of her cock from his lips and gently squeezed and stroked any last cum from her shaft onto his tongue. Sierra looked at him and said you are such a good little cumslut, thank you for that. He smiled and looked around before he stood up. He returned a few minutes later with our check.
Sierra smacked my stomach, and then kissed me. I than reached down and tied her limp cock back up. As I was doing that she reached over and grabbed my cock and realized that I hadn’t been satisfied yet. I just looked at her and said lets go to our bench, and her face lit up.
I didn’t want to ruin the night by telling her about having to leave, so I needed to make the most of our time. I didn’t tell her but I had asked for Thursday and Friday off to maximize the time we had left.
As we walked down the boardwalk the ocean was at high tide and the waves were crashing hard and making a lot of noise. There was a half-moon out and lit up the beach quite well so I told Sierra to stop and I bent over and took her heels off and I flipped my sandals off and said lets go walk on the sand. We walked down to the wet sand to make it easier and we walked for a while and realized that there was no one else around or any houses. We stopped and sat and just watched the waves come in for a few minutes and I just held her between my legs with my arms wrapped around her. After a little while I said let’s get naked and go in the water. She looked at me like I was crazy but I stood up and pulled her up. I lifted her dress over her head and took her panties and cock wrap off her. The moon on her skin was exquisite looking. She helped me out of my clothes but left my new cock ring and spreader on.
We walked into the water and it was cool but comfortable. We got about thigh deep and I kneeled down into the water and she straddle me and wrapped her arms around my neck and we kissed and ran our hands over each other’s bodies for what seemed like a long time. My cock was rock hard and hers was coming back to life as well. As we kissed I massaged her breasts and ass cheeks causing her to moan into my mouth as we kissed. We floated in closer to the beach and we laid down in the break next to each other kissing and fondling each other. The sand had begun to irritate our skin so we stood up and ran back into the water and rinse off. I scanned the boardwalk for a freshwater shower head and found one about 50 yards down the boardwalk. With no one around we just picked up our clothes and walked naked down the beach. The shower head had a light pole about 20 feet from it and gave us enough light to see what was around us. When I turned the shower on, it was freezing cold water and we both looked at each other and said fuck it and got in. It was fun and playful but it was much colder than the ocean. When we were done getting the sand and salt off of us, Sierra smacked my ass and told me to kneel on the nearby bench. I did what I was commanded and kneeled on the bench leaning over the boardwalk rail for support, Sierra stood behind me, rubbing my ass cheeks and then spanked me hard, I looked back at her and she said that was for the restaurant. Her fingers were exploring my new harness around my balls and cock. I was swollen and needed to cum, but I wasn’t allowed yet. She moved her hands up to my ass cheeks and spread them wide and spit on my hole. She began rubbing her spit into me trying to lube me up. Her fingers would push the spit into my tight hole each time she spit in me. After a few minutes of this I felt her stand up and put her right leg up on the bench and felt the large spongy head of her cock on my hole.
Sierra had just blown a massive load an hour before, so I knew that I was in for a long ride. I felt the pressure begin as she pushed into my barely lubed hole and it was intense. She pushed a little bit and then pulled back again over and over until she slid into my tight hole. Once she was in, she stayed in. Her hips made little small pistoning motions in my ring until I relaxed enough for her to push into me all the way. She started slowly long stroking my hole, it was an amazing feeling. She slow fucked me for a while, her hands wondering all over my body. She pulled me up to her and I was able to turn my upper body enough that we could kiss as her cock slid in and out of me. She would cup my chest and play with my nipples as well. She then told me to lie down on my back and she pulled her massive cock out of me.
I lay down on the bench the long way and she said no, she told me lay across it with my head over the back and to hook my feet onto the boardwalk rail. I looked at her and she smacks the head of my cock for not listening to her. It took me a minute but I did what I was commanded. My feet were way over my head and my ass was fully exposed to the world. What I wasn’t expecting was my own cock just inches from my face. Sierra, without hesitation, buried her cock back into my ass making me moan loudly. Each of her thrust down into me pushed my own cock closer to my face. Sierra stopped her motion and then stood on the bench above me and continued her assault on my ass, this time she was getting full penetration into me. The sensation and pressure in my ass was amazing, and I didn’t want her to stop. She fucked me like this for another 15-20 minutes, hard and deep. She would bring me to the point of cumming and then back off. I had precum leaking all over my face and mouth. Finally, I could tell she was about to cum again because she was pounding me harder and with shorter strokes. These shorter strokes pushed me over the edge and I blew a massive load all over my own face. A moment later Sierra sank her cock as far as it could go into me and filled me with a massive load of cum. She long stroked my ass for a moment slowly and then pulled out of me and she pushed my legs down and straddled my face and pushing her cock into my mouth for me clean up. She also would take the head of her cock and push my cum into my mouth until my face was just glazed over. She got off of me and sat on the bench next to me for a minute, both of us trying to catch our breath. We both jumped back into the cold shower and rinsed off and got dressed. I carried her shoes back to the car and we went back to my apartment.