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Introduction:

The end of an amazing relationship
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.

The next morning we woke up late and ate breakfast and had some light talk. I did my best to not show her my concern and just to make the time we had left fun and loving. We talked about the waiter the night before and joked that he would never be able to handle her big cock in his ass. She said that his mouth was very nice and soft, and we both had a laugh at that. We lounged around after breakfast and finally decided to go to the adult store a few miles away. We showered and dress scantily. When we got to the store we walked around looking at the videos and toys, making comments about both. When we got to the bondage section, we took our time and really explored the displays. Lots of butt plugs of all sizes and shapes, cock rings, body harnesses, gags, paddles etc. While we were looking around the manager, who we knew, came over and asked how I liked my new restraint device, I glanced at Sierra and she just smiled and said he helped me pick it out. I just responded that it was a little tight but it was nice. I actually was wearing it, and Sierra just reached over and pulled my cock out and showed him. He was a little surprised but not bothered by it. He asked if he could look closer and I nodded. He bent over and lifted my cock and balls and inspected the device and then let me go. He said that he hadn’t decided on getting one yet or not and wanted to see it on someone else first. I just shrugged my shoulders and said no problem with a little chuckle.

I reached over to Sierra skirt and raised it up exposing her massive cock and said do you have anything for this monster. We all chuckled and he said that he had got some new merchandise in that he thought she would like. He walked us over to a side room that was like plush changing room. He went to the back and came out with a box of items. He was digging through it and then came out with a bag of what looked like underwear. Sierra stepped closer to the table and he said that they were a male thong with a built in leg strap or tuck strap that was soft. As he spread them out on the table I saw a deep purple one and grabbed it, and said try this one. She looked at him and he nodded yes. She slipped it on and there was a pocket in the front for her cock to fit into and then she strapped it to the inside of her leg and snapped the strap. She looked surprised and said it felt amazing, it didn’t hurt like the one she wore. She then unsnapped it and asked how it worked tucked up. The manager looked at me for approval to help her and I nodded yes. He stepped behind her and reached between her legs and took the strap. He told her to tuck where she would normally go and tell him when he can hook it. She tucked her cock back and said ok, and he took the strap and adjusted to fit right at the top of the G-string. He didn’t tighten it down but just snug enough that it held her and the string didn’t sag too much. He told her to walk around and see how it felt. She looked amazed and commented on how comfortable it was. I asked him how much and he said if she allowed him to take some pictures of it in the different positions he would give it to us. He said the company didn’t send him any marketing photos of it and as beautiful as Sierra is, she would be perfect to model it. Sierra and I glanced at each other and she had those please eyes. I said sure why not. He left the room and I walked over to her and ran my hand over the material and I stroked her cock a little bit making it really stretch the material. For the next 30 minutes he posed her and took multiple photos of the one she had on plus some other colors. As promised at the end he gave her the purple ones to put back on, which she did. We spent the rest of the day walking around the mall and just enjoying each other.

Thursday came and went. On Friday, I knew I had to tell her soon. We spent the day, Friday, at her place, cleaning and her doing her nails and stuff. Friday afternoon, we were lying on the floor watching tv when her phone rang. I looked at her and she said only her parents have her number. Now my brain was going a thousand mph. Sierra, Answered the phone and immediately said “Hey daddy” I could feel my heart thumping my ribcage. They talked to for a moment and then she looked at me and handed the phone to me. I said hello sir and he asked how we were doing. I told him we were great and then he told me not to react to what he was going to tell me. He told me that her ex actually knocked on their door and was raging mad that I attacked his private detective. He said he wanted his film back and he wanted to see Sierra, and now that he knew she was still somewhat local that he planned on finding her. Her dad said he called the cops and had a trespassing order put on him for their house but couldn’t do it for Sierra’s or my apartment. Her dad asked me if I still had the film and I told I did. He said good don’t lose it. As non-de*********** as I could I said I wouldn’t. He then told me that he would break the news to her on Saturday afternoon, letting us have the rest of the day to each other. I just responded, yes sir, and said good bye.
1 comments

ncbiguyReport 

2025-02-13 19:41:29
why the negative votes?

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