Daughters Boyfriend Serves an Ace
I was laying there in some very transparent red lace panties and Drews’ tee shirt. Head was really confused with my body and my spontaneous reactions to my conversations with this cute teenaged boy one bed over. Only hours before I was in a conservative night gown that more that covered me down to my knees. I felt both guilt and passion as I heard him sleeping on the next bed over from in our very upscale hotel room. I balled up in a fetal position with my mind on my wet crotch and very hard nipples. I am not sure when but I finally fell asleep.
So I am Anna. I am a 44 year old mother of an 19 year old girl and an avid tennis player. Last summer I started playing tennis with my daughters boyfriend, Drew, and we began to enter into tennis tournament and win at the club and state level. Drew is a great player we just seem to work well together on the court. I have kept playing regularly since playing in college but my skill has faded some with age and I do practice law.
Over the past two years we have played a lot and trained a lot together and I have become great friends with his mom, a single parent, and Drew. We have both had minor injuries and become a little closer and we have had to massage each other at different times and different parts of our bodies. Which have made for some embarrassing moments and I have caught glances of things most moms of teenage girls don’t see of their daughters boyfriends which is also why I became so focused on him in both curiosity and maybe some lust. During a pulled growing muscle injury I would help rub his thigh adn when you massage a teenaged boys thigh things do pop-up and boy did they.
That is when I first noticed that eh was really gifted and I don’t mean for a boy but foe a man. He has also helped me with a few sore muscles and his massages stirred things and caused some excitement that was more than just friendly desires. I also began to notice that he was checking me out as you would expect a boy to do. He would steal glimpses at my ass, crotch and chest. At first I would try to slowly change positions to remove the temptation but over time I began to wear more revealing tops and tennis skirts and panties rather than shorts which afforded more opportunities.
I was actually getting turned on by his checking me out and I would begin to give little shows and play it off as accidents especially bending over and showing him my ass or in front of him so he could see down the v of my top. I would even wear just a sports bra to practice in the summer and watch him try to sheepishly check out my rock hard nipples. I am a 5‘8’ tall and measure 32C (sometimes a D), 22, 31 with dark brunette hair.
Three weeks my daughter broke up saying that she wanted to go away to school, she is older than Drew, with out and attachments and about the same time Drew and I entered into the state tennis open challenge and surprised everyone, even ourselves, by winning through the first rounds. Since we had to travel across the state for the last matches, we left for the tournament on Thursday to be well rested. Drew’s parents are divorced and rather than have two rooms and the expense we just got one room with tow beds. I took the traditional mother type sleeping gown and just figured he would sleep in shorts.
That first night I was laying in bed extremely uncomfortable since I typically slept in a thin gown and panties and hated the material around my body. I noticed that Drew was stirring around so I asked him if he was ok and found out that he typically just slept in boxers, not shorts and a tee so I made a deal. He would give me his tee and then he could sleep in just his boxers. After all, we were in different beds. He took off his tee and tossed it to me and I heard his shorts hit the floor right after that so a removed my gown, the room was dark so I just sat up in bed and pulled it off over my head and chucked it on the floor, and started to put on his tee.
As I did, my body just froze there and I got so excited that my nipples got rock hard and I shivered and came or maybe peed a little. I glanced over and saw Drew was looking my direction but other than my partial naked silouette, it was too dark to make the details out, he couldn’t see anything ..did i want him to?
We chatted for a while about life, dating and I did my normal teasing him about girls, my daughter and that I knew he was a boob man and who he thought he should ask out, know he was a boob man, but coming from his former girlfriends mom that may have been strange even though I did know him well and he know I would keep it a secret. Secretly, I was glad he didn’t have plans. I knew he was a virgin but he and my daughter had gone to third base a few times and I also know that he has a sizable manhood both from seeing it pop-up as I mentioned before and overhearing my daughter tell her friend that Drew’s penis was larger than her wrist and really long and much larger than her dads. So when had she seen my husband Tim’s dick ..a question I wanted to ask but never could figure out how so I just assumed she had walked in on him changing or showering and let it go. I was actually getting horny laying there in bed.
Some background. I caught her dad Tim, a physician, in bed with a friend and tennis partner of mine. I walked in my living room to see her totally riding his cock as he sucked her tits. I actually saw him fill her bald pussy with his sperm since I was in shock and couldn't move to leave. She was a screamer, a squirter and he said he liked her shaved pussy and DD tits. I heard later she liked it in the ass too. if that wasn’t enough, I later caught him fucking a rather large, bbw, big tit latin intern in his office on his desk. Her pussy was hairier than mine and I watched her tits sway back-n-forth as he hammered her. She was a virgin when they met but was a pregnant slut when the summer was over and she returned to school. Rather than divorce, we decided to wait until our daughter had left home for school and he would just file for divorce and move out.
Back to my story ... Eventually I heard Drew sleeping on the next bed over and I too soon fell asleep all cuddled up in the fetal position with a wet crotch and very hard nipples.
I awoke the next morning and, believing he was still sleeping, walked over to the window to see the city and stretch to wake-up. As I stretched my arms over my head, which raised the tee shirt up to my waist, I gave a now wide awake Drew a full view of my 44 year old ass in tight almost transparent lacy red panties. My mind was somewhere out there thinking about my upcoming match and my growing attraction to my daughters former boy friend when Drew, said this is was sure a nice view! I almost jumped threw the roof! I turned around to see him up on his elbows looking at me.
I told him that he almost scared the pee out of me and as I walked across the room to go to the bath room his eyes totally covered my body and his complement about looking as good in the morning as I always do threw me so I had to ask to to verify that it was a complement. He did and asked if I had been up for a while to which I said no and that is why I have to go to the bathroom. He said don’t be long I have to go too and that is when I believe he caught me staring at the large lump growing larger under the covers. He looked down following the path of my eyes and was looking back at me when I turned the corner to the bathroom. I just said boys and the morning stiffey as I closed the door ..I couldn’t believe i said that!
I really had to go and just the though of him knowing I was peeing was erotic. When I was done I walked out of the bathroom and told the beautifully built and bare chested Drew who had an obvious morning erection that the bathroom was all his he wasted no time and with out even closing the door I soon heard the steady stream of his pee into the toilet. Without thinking, I walked to the door to initially see the back of him but turning to look at him in the mirror I saw the side view of him holding a very large penis and guiding a steady stream of pee into the toilet.
My knees weakened and I saw him catch me in the door but rather than say something like “can’t I pee in private” he apologized for leaving the door open. I went to sit on the foot of the bed and turned the television on to try to clear my mind as I heard the shower start and stop. As he came out of the shower with a towel around his waist, a nice bulge in the front and water still on his tan well-built body it was my turn to say nice view with a wicked grin and I watched him smile as he once again checked me out as i walked past him to take a shower and dress.
In the bathroom I took a long look at myself in the mirror and I was clear why my teenaged Drew was sporting a rock solid hard-on. His tee shirt clearly did not hide the shape of my rock hard nipples and it was not long enough to cover the bottom half of my panties, front or back. My exposed red panty 1/2 covered ass cheeks in the back and a bunch of my bush was escaping around the sides of my panties in the front and clearly visible through the lace. I was actually wet ... still wet or again yet to be determined.
We won both matches that day although Drew was much more off his game that normal. We were scheduled to play our semi final match that night under the lights.
After some dinner we went to the locker room they assigned us to change and prepare for our night match. It wasn’t too much more than a large single stall bathroom with an open shower with no door. After giving the room a once over, Drew said that he would wait outside but I told him it was fine and started to get ready to shower and change. I said I would go first and told him not to look as I began stripping down. My knees were actually shaking, my nipples once again stiff (the cool locker room didn’t help) as I wrapped a towel around my nude body and walked to the shower.
Since there was no shower door of curtain I have no Idea why I wrapped myself in a towel. I caught him looking and scolded him but it came across as a joke as we both laughed and he denied it .....but had no answer as to why I was looking at his face if he wasn’t looking at me. As I took a shower he stripped and I had a clear view for the first time of his very large penis. It was semi hard with a very large head. Its girth and length were much larger than I imagined and although it was long ..it was extremely thick. . Since there was no shower door I am sure he got a clear view of my C cup breasts with large dark red nipples, with tight stomach and firm ass from hours of aerobic and biking and my thick dark busk that, well let’s just say it is thick but trimmed only enough to wear tennis panties.
I finished my shower and told him it was all his and wrapped the towel around me to step out of the way so he could get in. He turned the water on and dropped his towel to reveal a very stiff and fat penis that was now sticking straight up at the sealing. It caught my full attention and when he saw i was looking he reminded me of my promise but I told that if he had kept his part of the promise he would not be in his present situation. In a motherly voice, the best I could muster at the time, I told him he might want to make the water colder as that might help. He didn’t laugh but did change the water.
Ok, it was now that I wanted to walk over and join him knowing fully that if I did I would surely have ended up on my back in the floor at some point with a teenaged penis thrusting in me .. which actually was appealing to me at this point. With adult reason, finally, I dried off and dressed but this time I was really not trying to cover myself and used little modesty. He completed his shower and dressed still sporting an erection that would have made any woman blush. He was quiet for a while and eventually the amazing erection he had went away long enough for us to play a very long match that we eventually won. After the match I gave him a big hug and a light kiss on his lips rather than the cheek which I usually did.
We found out that the final wasn’t until the following afternoon since the other semifinal wouldn’t be played until the next morning and left for the hotel. The ride was quiet and I was not sure what he was thinking but I was sure thinking of what I did and what I did to him in the locker room. l broke the silence but telling him that I should not have stripped in front of my daughters former boy friend but I just thought that he was old enough to be mature and this needed to be our secret. He said it was alright with him and he apologized for what had happened and but when I said nothing happened he referred to his erection and I told him that it was my fault and at some point and I should have expected that to happen and any way .. he had nothing to be ashamed of there either. he looked at me strange but then smiled and said thanks.
We both showered dressed and grabbed a snack when we got back to the hotel room. I tried to keep it light hearted as possible and reminded him of our secret when I turned out the light and started getting ready for bed. I asked for his tee shirt again and slipped it on after I had stripped completely nude. I felt so horny and so naughty as i slipped into my bed. I couldn’t believe i had just removed my panties and shorts both and now I could feel the clod sheets on my bare ass. So what would he say tomorrow if it was my bare ass he saw in the morning and not lacy panties?
We were talking when I asked him what color were his boxers and he asked me why and then said that he would tell me if I would tell him what color my were. I asked him if he liked my lacy red panties and he said they were nice but when i asked him why, he became quiet for a while, then answered that they were sexy. I cleared the lump out of my throat and finally got the courage to ask him if he liked what he saw in the shower this evening or what he saw this morning better. Once again got quiet before answering “this evening in the locker room but you also looked nice this morning”. I told him good, liked what I was too.
I reached over and turned the bed side light on which surprised him but what I did next surprised him more. I got out of bed to reveal that I had a bare ass and walked towards his bed. From his angle laying in bed, I knew he was looking right at my uncovered bush. I pulled his tee shirt over my head exposing my nude body to him and pulled up his covers and slid into bed with him.
Our bodied embraced and I would feel his warm body against mine as we kissed deep and I held him close. He took over and kissed his way down my neck, ears and to my breasts which threw me over the edge. He gently rubbed and tweaked one nipple as he sucked the other making sure he alternated frequently. I removed his boxers and drove my tongue down his throat as i grabbed his penis for the first time. He was over 7.5 inches long and so thick I was unable to get my fingers completely around it. The base of his penis as the thickest part of the shaft and his balls were large. Even more impressive was the large mushroom shaped head that, now coated and dripping in precum, was even wider that the base. My husbands penis was not near this large.
I rolled over on my back and puled him over on top of me and, as I hoped, he offered no resistance. I had intended to just fuck him but he surprised me again by starting to kiss my neck and work his way down my body again. After kissing my ears, neck, shoulders, chest, breasts, nipples, stomach and inner thighs, he found my dripping wet pussy and clit.
My husband had never gone down on me and, even though I was certain Drew was not experienced. His lips and tongue traced the lip of my vagina and clit and he would frequently push his tongue inside of me and run it around the inside of my vagina before sucking my clit and then starting it all over again. With my hands on his head, I held him tight and humped his tongue and mouth as my orgasm neared and I rewarded his efforts with an earth shattering orgasm that rocked the room and filled his mouth with cum.
He worked his way back to my lips and I told him that it was awesome but we both soon laughed as he began pulling pussy hair off his tongue and from his mouth. I apologized but he kissed me deep before responding that I was beautiful, I tasted great and he liked my sexy hair “down there”. So there I was ... my daughters teenaged boyfriend had just eaten my pussy and given me the first orgasm I had ever had other than through self masturbation and I was being told I was beautiful, sexy. He even liked my hairy bush and the taste of my cum.
I continued to taste my cum as we kissed, but I soon needed more and I raised my knees and reached down to guide his penis to the opening of my very wet pussy. I had never had such a large dick in my hand as my husbands dick is the only one I have ever held or fucked and it is shorter and much thinner. He took over and guided the large head of his penis back and forth across the wet lips of my vagina mixing my cum and his precum together for the first time, I was on fire. He slowly pushed and I began to feel the thick head of his penis stretch me open as he entered me.
His long thick penis was disappearing into my hairy wet pussy and God it felt good. Our tongues danced together as he began working deeper inside of me and I soon broke the kiss to tilt my head back and moan as his thick penis began stretching the lips of my pussy wider and the head of his dick was going so deep. His breath became shallow and he whispered he was sorry but he wouldn’t last and began picking up the pace and pushing deeper.
My head was spinning but I told him that I wanted him to cum inside of me, something that I had never verbally sever said to my husband, and with my hands on his ass, I pulled him deeper in me. He had his arms around me pulling himself deeper into me and my heels now firmly dug into his ass .. he let out a low moan and his penis began to pulse deep inside of me.
The pulses of his large penis were amazing and I too began to orgasm as I felt a warm douche like feeling as his hot cum began to fill my belly. I had never felt that feeling and it seriously rocked my world. The amount of cum he deposited into my totally unprotected pussy was incredible and it wasn’t until then that I remembered that I wasn’t on birth control but I told myself that I didn’t care.
I had just taken my daughters boyfriends virginity, I had orgasmed on his face, cum on his incredible dick, had two earth shattering orgasms, had my unprotected pussy totally filled with his cum and with all probobility just gotten pregnant. . We lay there for a while motionless until he began to push his still large 3/4 stiff penis into me again. He raised up on his elbows and pushed deep and soon the lips of my pussy were surrounding the base of that giant penis and his large hairy halls were bouncing against my ass. He lasted longer and began pushing hard and deep causing me to moan.
His cock became fully hard again as it pushed in my extremely wet vagina and with a few hard thrusts he orgasmed for a second time but this time he was in me balls deep and the head of his penis was shooting his load directly into my womb. Pulse after pulse of warm seaman flooded my womb as he moaned in my ear.
We lay in each others arms with the only movement being a sudden spasm of his penis or the muscles of my vagina as it still gripped his softening manhood. He eventually pulled out, rolled on his back and we fell asleep with his arms around me and my head on his shoulder.
The next morning i awoke still in his arms and felt a strange calm and peace about me. The light of day filled the room and I looked at his in a different light. I got out of bed and felt his cum begin to run out of me and down my inner thigh as i went to the bathroom to answer natures morning call. I jumped in the shower and eventually opened the door to see his naked tight cute ass as he peed into the toilet. He had a morning woody and looked so sexy for some reason. I stepped out of the shower and saw him look at me like I had always wanted to be looked at an our flesh against flesh daylight hug and morning kiss was amazing. I told him that if we won we might have to stay another night so he better be thinking about fuzzy yellow tennis balls and not my breasts ..
..well we won and I stuck my tongue down his throat right there in front of the world and that next night I got a second and third helping of his hot cum deposited deep in my pussy after coating his dick with my cum from a few earth shattering orgasms. I loved straddling him and feeling his large penis in me and his hands on my firm ass pulling me down on him. He said that he always wanted to feel my ass since he looked at it so much playing tennis and now it was all his.
He told me how he had masturbated many times thinking about it but when I asked him about my daughter and third base he said she liked oral (so that is how he was soo good) and she liked to lick and suck the head of his penis until he would cum. He said one time she had him cum on the crotch of a pair of my panties and I wore than the next day. Well, I wear Drew’s cum on my panties a lot now but that is because if leaks out of me. If my friends knew then I was fucking Drew they would never speak to me so we just kept it a secret.
My daughter figured it out when she came home and saw her four month pregnant mom riding her former boyfriends penis on the living room couch. At first he hated me but now i share Drew and she too is pregnant.
He is a great lover and gives the best kisses and massages I have ever had.
Hilary shows her grandmother that she didn't miss her chance to explore her sexuality after all...
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