Been a while since I have posted a story! This one’s a bit long, but bear with me as I tried to capture all the details of this adventure. This one happened in April of this year, and I am just getting around to sharing it. Although we have played with other men, it has always been with someone we know (my friends, our trainer). We were planning a quick trip to Las Vegas in early March, and I proposed to her it would be a huge turn-on to have her get a massage in our room while we were there. Deb was reluctant at first, but at one point asked me, “how would we even go about finding someone I would be comfortable with?” – I quickly told her that I would handle that and to trust me to get someone she would like. She was hesitant but said she would try.
Fast forward to 3 weeks later, I had placed an ad on Wifelovers looking for an erotic massage and got several replies quickly – I landed on a guy (we will call him Steve) who was early 40’s, great shape, and an 8” cock. Told him that she was willing but nervous and that she would determine how far it went and could end it at any time. He said he had experience with this situation and there was no pressure.
We got to our hotel and spent day one just exploring, seeing a show, and having dinner – I had set up the massage for the second day. Deb had been a little nervous when I asked her about it but told her we would do a relaxing day at the pool, have some drinks, and then she could fully relax for a private massage. I purposefully avoided any sexual contact with her for several days as I wanted her nice and horny for the massage.
We woke up and went down for a breakfast and started the day off with a couple of mimosas. We then put our suits on and went down to the pool for the day – with great chairside service we were rarely without a drink, so when 4pm rolled around she was well lubricated and relaxed when I told her it was time to go upstairs for her massage at 4:45. She didn’t seem to have any second thoughts, and up we went. I suggested she might want to grab a quick shower before he got there, and she did that coming back into the room in a robe and nothing else! I kissed her and told her to relax and enjoy – which made her kiss me harder and grab my dick!
Steve call me at 4:40 and told me he was at the elevator banks, so I went down to bring him up. Seemed like a great guy, good looking and fit which I knew would turn her on. Went thru the rules with him again and we arrived at the room.
I introduced Debbie to Steve, and she greeted him with a big smile – he kissed her hand and told her how tanned and relaxed she looked…she blushed but know she was impressed with him. We had some small talk, and then I asked him what we needed to do to get started – he said he wanted to wash his hands and asked that Deb to lay on the bed with her robe untied but on her and he would be out. She laid down and I draped the robe over her nude body, and I could tell by her protruding nipples that she was already turned on!
Steve came back out in his sweats and a t shirt and told Debbie he would be using a massage oil and would start on her back, working his way down to her feet. She nodded and lay there with her eyes closed as Steve took off his shirt to get started (pretty buff guy with well defined muscles!). He started on Deb’s shoulders, and I could tell she was enjoying it, with an occasional sound as he hit the sore spots on her back and shoulders. Once he finished her back, he covered her back up and then moved the robe up from the bottom to massage her feet and legs. He worked her feet and calves and worked up her legs, stopping to pull the robe back up over her ass – this was a “moment of truth” and Deb did not move or protest. Steve rubbed up her leg to her thighs, gently pushing her legs apart more as he worked up. He then moved up to her ass and started some deep tissue motions on each cheek – Deb moaned a bit, letting him know she was enjoying it.
I was sitting in a chair at the end of the bed, and I had a straight shot view of her pussy – and I could tell as he was rubbing her ass, he was getting a close-up view of her pussy lips and asshole. As he moved back down to her legs and thighs, I noticed he told her to relax as he slowly brushed her pussy lips with his hand on each move further up – Deb moved her legs a little further apart, which was a sign to both of us that she was in a good place!
Steve stopped and cupped his hand over her pussy, slowly moving his hand in circles – I even saw his finger slowly move up and down her slit, and she was not protesting at all. Steve stopped and asked her how she was feeling, and she mumbled “really good”, to which he smiled at me. He then said, “I’m going to lift your robe toward me, when I do roll over on your back”, which she did. She opened her eyes and saw him kneeling there with his shirt off and all she said was “wow!”. He had a light sweat glaze on his neck and chest from the work and asked if it would be ok if he took his sweatpants off as he had compression shorts on underneath. I said I was fine, and she said sure, so he pulled them off. I could see the bulge of his cock thru the shorts and could tell he was enjoying the massage as much as she was.
Steve moved up above her head to start massaging her there, and worked her head, temples, ears, and neck – Deb had her eyes closed and seemed to be enjoying it – he moved from her neck down to her shoulders, and from her shoulders to her upper arms and upper chest. I was surprised how quickly his hands moved to the side of her boobs, and then up over her breast and nipples – Deb twitched for a second but did not open her eyes or resist. Steve slid the robe down below her tits and rubbed oil on her firm and erect tits and nipples – Deb moaned very lightly as he touched her sensitive nipples with each motion. After what seemed like forever massaging her breasts, Steve pulled the robe up and moved around to her side to massage her feet and legs – he pushed the robe up to just below her upper thighs and worked each foot and leg pretty well. I knew what was coming and was already incredibly hard myself!
As he worked his way up her inner thigh, I saw Deb move her legs further apart, giving him a bird’s eye view of her pussy – he moved the robe up to her waist, and worked her hips and lower stomach with her bare pussy in full view. I was loving this as much as she was, and it got even hotter as he pulled the robe covering her breasts down so that both she was fully exposed. He put more oil on his hand and began gently massaging around her swollen lips, running his middle finger up and down her pussy and slowly rubbing as he touched her clit – Deb shuddered when he did this and he moved his other hand up to her titties, slowly massaging around her nipples as he fingered her pussy – he asked her if she was ok and if it felt good and she just said, “uh huh” as he continued. Pretty quickly I saw his middle finger disappear and know he had it deep in her…moving it in and out while he used his thumb to rub her clit. I could hear Deb’s breathing get heavier and I had to pull my cock out and begin stroking it as he was fingering my wife.
Deb laid there with her eyes closed and moved her hand up to his leg as he started moving his fingers quicker in her pussy – she moaned, and almost seemed to arch her back a little for him to access her. She turned her head towards him and said, “what about this?” as she reached over to his extremely hard cock and took it in her hand thru his shorts. He chuckled but moved a little close to her as she stroked him. I was busy watching him put two fingers in her pussy and did not realize that she had reached in his shorts and pulled his dick out, stroking it pretty good! Steve asked her, “I’d love to use my tongue instead of my fingers on you if you are ok with that”….and Deb didn’t even open her eyes…just said “yes!” as she let go of his cock. Steve quickly moved between her legs, and kissed her thighs right up to her pussy, where he slowly used his tongue to part her pussy lips and flick her clit. This droves her crazy and she grabbed his head and pulled it into her pussy….and came very quickly as he flicked her with his tongue to climax. She seemed cum forever, but eventually pushed his head away and he moved back to her side, rubbing her leg and arm slowly as she came down from her high.
Deb reached back over to his cock and was stroking it again (he was fully erect now and excited. To my surprise, Deb turned on her side and moved her head down to his cock, where she kissed his head and then slowly started sucking on it as she stroked him. Steve was really enjoying it, and I very quickly came all over myself watch her suck his dick while she was fully nude. It did not take too long, and I saw Steve start to stiffen up and push his cock into her mouth – as he started to come Deb pointed him towards her breasts and he came all over her boobs…I had never seen so much cum from on orgasm! She laid back down and Steve told her he needed that, to which she replied, “so did I!”, which we all laughed at. Deb got up and got cleaned up, and Steve did as well. We all said goodbye and he told us to call him anytime – I walked him out as Deb hopped in the shower – my fantasy, and her first erotic massage, now a reality!!
Fast forward to 3 weeks later, I had placed an ad on Wifelovers looking for an erotic massage and got several replies quickly – I landed on a guy (we will call him Steve) who was early 40’s, great shape, and an 8” cock. Told him that she was willing but nervous and that she would determine how far it went and could end it at any time. He said he had experience with this situation and there was no pressure.
We got to our hotel and spent day one just exploring, seeing a show, and having dinner – I had set up the massage for the second day. Deb had been a little nervous when I asked her about it but told her we would do a relaxing day at the pool, have some drinks, and then she could fully relax for a private massage. I purposefully avoided any sexual contact with her for several days as I wanted her nice and horny for the massage.
We woke up and went down for a breakfast and started the day off with a couple of mimosas. We then put our suits on and went down to the pool for the day – with great chairside service we were rarely without a drink, so when 4pm rolled around she was well lubricated and relaxed when I told her it was time to go upstairs for her massage at 4:45. She didn’t seem to have any second thoughts, and up we went. I suggested she might want to grab a quick shower before he got there, and she did that coming back into the room in a robe and nothing else! I kissed her and told her to relax and enjoy – which made her kiss me harder and grab my dick!
Steve call me at 4:40 and told me he was at the elevator banks, so I went down to bring him up. Seemed like a great guy, good looking and fit which I knew would turn her on. Went thru the rules with him again and we arrived at the room.
I introduced Debbie to Steve, and she greeted him with a big smile – he kissed her hand and told her how tanned and relaxed she looked…she blushed but know she was impressed with him. We had some small talk, and then I asked him what we needed to do to get started – he said he wanted to wash his hands and asked that Deb to lay on the bed with her robe untied but on her and he would be out. She laid down and I draped the robe over her nude body, and I could tell by her protruding nipples that she was already turned on!
Steve came back out in his sweats and a t shirt and told Debbie he would be using a massage oil and would start on her back, working his way down to her feet. She nodded and lay there with her eyes closed as Steve took off his shirt to get started (pretty buff guy with well defined muscles!). He started on Deb’s shoulders, and I could tell she was enjoying it, with an occasional sound as he hit the sore spots on her back and shoulders. Once he finished her back, he covered her back up and then moved the robe up from the bottom to massage her feet and legs. He worked her feet and calves and worked up her legs, stopping to pull the robe back up over her ass – this was a “moment of truth” and Deb did not move or protest. Steve rubbed up her leg to her thighs, gently pushing her legs apart more as he worked up. He then moved up to her ass and started some deep tissue motions on each cheek – Deb moaned a bit, letting him know she was enjoying it.
I was sitting in a chair at the end of the bed, and I had a straight shot view of her pussy – and I could tell as he was rubbing her ass, he was getting a close-up view of her pussy lips and asshole. As he moved back down to her legs and thighs, I noticed he told her to relax as he slowly brushed her pussy lips with his hand on each move further up – Deb moved her legs a little further apart, which was a sign to both of us that she was in a good place!
Steve stopped and cupped his hand over her pussy, slowly moving his hand in circles – I even saw his finger slowly move up and down her slit, and she was not protesting at all. Steve stopped and asked her how she was feeling, and she mumbled “really good”, to which he smiled at me. He then said, “I’m going to lift your robe toward me, when I do roll over on your back”, which she did. She opened her eyes and saw him kneeling there with his shirt off and all she said was “wow!”. He had a light sweat glaze on his neck and chest from the work and asked if it would be ok if he took his sweatpants off as he had compression shorts on underneath. I said I was fine, and she said sure, so he pulled them off. I could see the bulge of his cock thru the shorts and could tell he was enjoying the massage as much as she was.
Steve moved up above her head to start massaging her there, and worked her head, temples, ears, and neck – Deb had her eyes closed and seemed to be enjoying it – he moved from her neck down to her shoulders, and from her shoulders to her upper arms and upper chest. I was surprised how quickly his hands moved to the side of her boobs, and then up over her breast and nipples – Deb twitched for a second but did not open her eyes or resist. Steve slid the robe down below her tits and rubbed oil on her firm and erect tits and nipples – Deb moaned very lightly as he touched her sensitive nipples with each motion. After what seemed like forever massaging her breasts, Steve pulled the robe up and moved around to her side to massage her feet and legs – he pushed the robe up to just below her upper thighs and worked each foot and leg pretty well. I knew what was coming and was already incredibly hard myself!
As he worked his way up her inner thigh, I saw Deb move her legs further apart, giving him a bird’s eye view of her pussy – he moved the robe up to her waist, and worked her hips and lower stomach with her bare pussy in full view. I was loving this as much as she was, and it got even hotter as he pulled the robe covering her breasts down so that both she was fully exposed. He put more oil on his hand and began gently massaging around her swollen lips, running his middle finger up and down her pussy and slowly rubbing as he touched her clit – Deb shuddered when he did this and he moved his other hand up to her titties, slowly massaging around her nipples as he fingered her pussy – he asked her if she was ok and if it felt good and she just said, “uh huh” as he continued. Pretty quickly I saw his middle finger disappear and know he had it deep in her…moving it in and out while he used his thumb to rub her clit. I could hear Deb’s breathing get heavier and I had to pull my cock out and begin stroking it as he was fingering my wife.
Deb laid there with her eyes closed and moved her hand up to his leg as he started moving his fingers quicker in her pussy – she moaned, and almost seemed to arch her back a little for him to access her. She turned her head towards him and said, “what about this?” as she reached over to his extremely hard cock and took it in her hand thru his shorts. He chuckled but moved a little close to her as she stroked him. I was busy watching him put two fingers in her pussy and did not realize that she had reached in his shorts and pulled his dick out, stroking it pretty good! Steve asked her, “I’d love to use my tongue instead of my fingers on you if you are ok with that”….and Deb didn’t even open her eyes…just said “yes!” as she let go of his cock. Steve quickly moved between her legs, and kissed her thighs right up to her pussy, where he slowly used his tongue to part her pussy lips and flick her clit. This droves her crazy and she grabbed his head and pulled it into her pussy….and came very quickly as he flicked her with his tongue to climax. She seemed cum forever, but eventually pushed his head away and he moved back to her side, rubbing her leg and arm slowly as she came down from her high.
Deb reached back over to his cock and was stroking it again (he was fully erect now and excited. To my surprise, Deb turned on her side and moved her head down to his cock, where she kissed his head and then slowly started sucking on it as she stroked him. Steve was really enjoying it, and I very quickly came all over myself watch her suck his dick while she was fully nude. It did not take too long, and I saw Steve start to stiffen up and push his cock into her mouth – as he started to come Deb pointed him towards her breasts and he came all over her boobs…I had never seen so much cum from on orgasm! She laid back down and Steve told her he needed that, to which she replied, “so did I!”, which we all laughed at. Deb got up and got cleaned up, and Steve did as well. We all said goodbye and he told us to call him anytime – I walked him out as Deb hopped in the shower – my fantasy, and her first erotic massage, now a reality!!
